Interviewed in April 2026. This conversation has been edited for clarity and brevity.

 west & ease is a space for conversations with creatives, insights on design, and the moments that bring community to life. I’m Leslie Luo, and I’ve always been fascinated by how we interpret the world. And west & ease is where I explore that through conversations, design, and community.

Today I’m talking with Eric Li, a self-taught designer, developer, and co-founder of Versive, a YC-backed AI user research platform. Eric started his career in investment banking, then made a deliberate pivot into product, designing at Bread as their first designer, at Uber Eats, and leading product and design at Vareto before starting his own company, Versive.

Recently, he built Scratch, a free open-source markdown notes app, all in a weekend using AI coding agents and watched it blow up on GitHub, LinkedIn, and Twitter. We get into his actual workflow with Claude Code. Why design taste is still the hard part, even when AI can ship working software in minutes, and what building in public looks like when you’re already running a company.

To learn more about Eric and his work, visit www.ericli.io or follow him on Linkedin and Twitter.

You can also read our first conversation, where Eric shares more about his creative journey.

west & ease is part of & luo studio, where I do fractional design consulting, design coaching, and host creative community events. If you’re a brand, team, or creative partner interested in collaborating, I’d love to connect. You can learn more and reach out at www.andluo.studio.

Credits

Music by lsaudio from Pixabay

Meet Nirupa Konijeti, founder and host of Bazaar Supper Club and Bazaar Butter, a monthly supper club held in her Brooklyn apartment, where she gathers ~18 people for a delicious family-style feast and deep, intentional conversation. With a 10,000+ person waitlist for her dinners, Nirupa’s dream of creating a community she envisioned stemmed from a pivotal moment in 2023, when she got laid off from her job, a day after manifesting freedom in a vision board exercise. From scrambling to finding a new job to getting creative with tapping into her childhood dream of working with food, Nirupa shares how she experimented to see what would stick to continue to grow and evolve what became the initial versions of what would eventually become Bazaar Supper Club in 2024. Above all else, she’s learned that being her authentic self, showing up with her why, and welcoming folks of all walks of life to build intentional community not only instills confidence but also enables her to become a better villager. After all, in Nirupa’s words, to build a village, you must become a villager.

Interviewed in January 2026 | This conversation has been edited for clarity and brevity. Heads up, the interview contains some explicit language that may not be suitable for all audiences.

Tell us a bit about yourself. I’m Nirupa. I’m in my thirties, and I work in food. A second part of me works in finance, but I primarily want to be seen as someone exploring her creative pursuits and trying to make her inner child happy. That’s my only mission in life right now.

I grew up in South India for 20-ish years and spent the last 10 in the States. These last 10 years have been me building my life from scratch, and as a child of immigrants.

2025 has been my most transformative year. I want to tell the story of how you can truly change the trajectory of your life if you throw your all at it.

Let’s start by picking a moment in time to help us understand why 2025 was a super transformative year for you. Three years ago today, I was working as a Product Manager at a tech startup, and I was so miserable. I was not happy, and I also felt very trapped doing what I was doing. I had made a vision board, and one of the messages was a woman sitting on a farm with a dog. It was alluding to freedom. And the next morning, I got laid off. The universe handed me what I was hoping for, but I was not ready for it.

On the surface, my focus was survival. Find another job. Stay in the country. Keep things moving. But underneath that, something much deeper had started to shift.

That period changed how I saw everything, especially the idea of “community.” I started to notice who showed up, how they showed up, and also where things felt misaligned. It was more of a quiet realization that the version of support I needed didn’t always match the relationships I had built up until that point.

And as an immigrant, that realization hit differently. When you build a life far away from home, you place a lot of meaning on the people around you. You want that sense of chosen family. You want a village. What I learned was that a village isn’t something you just find. It’s something you build. And if you want a village, you have to be a villager.

So I started there. I began looking beyond the circles I had known, staying open to new people, new spaces, new ways of connecting. I didn’t fully know what I was looking for, just that I was ready to build something that felt more aligned with who I was becoming.

And that search ended up changing the entire direction of my life.

When I was growing up in India, I had a strong inclination towards food. I just never had a chance for it to take off when I finished college in 2014. I went to my dad and told him I wanted to be a pastry chef, and he basically said, “Absolutely not.” That dream got killed right there. I didn’t have enough background to support the ask, so I just let it slide and never picked it up.

I came to the States, built a career in tech, and I’m very happy with what I did with that. But I always felt like I had something I never fully explored sitting in my backpocket.

And so, when the layoff happened, I had about six months of free time between jobs that I could truly use the way I wanted my days to look. My time was all mine, and that was when I was asking myself, “What do I want to do?” I have this deep idea of community, and also this dream of food that I never got a chance to explore fully. How do I bridge these two things together and try something out?

That was also when I started noticing a big shift in third spaces within New York. I did a lot of research for a month or two, looking at all the different third spaces, and I noticed there were not enough. I wanted to create one. That was the first pivotal observation I had: to create a third space with food and people. And specifically, how was that going to shapeshift dinner parties? That was the idea where dinner parties came to me.

Now, onto execution. Like, who the hell is going to come to my dinners? I’m just an average cook living in New York. So, I started FaceTiming my mom and made her teach me all her recipes, and I retrained myself as a cook because I had time in my day.

I also started looking into what platforms I could use to host dinner parties. I tested out a couple of third-party platforms, like Airbnb Experiences. I did that for a while, hosting tourists visiting New York. But they weren’t grounded in New York. Correct. But I needed to exercise my skills.

I bought foldable tables, plates, and glasses, and I started by teaching cooking classes. I even went up to my building management because they sometimes host events for residents. I noticed that they could do more. So, I went up to them and said, “I live in the building, and I have this idea.” They said, “Do it.” Wait, I love that! And so, they were paying me to throw events for the building community. It was also a great way for me to practice. I did that for a couple of months, and it was me throwing stuff at the wall and seeing what stuck.

Bazaar Butter

My Entire Dinner Party Collection — What I Actually Use for 18 Guests

Hi friends…

Read more

5 months ago · 19 likes · 1 comment · Bazaar Butter

Then, I decided to pivot to dinner parties. I wanted to take it back to people sitting around a dining table with no end time. With dining in New York, you typically get 90 minutes. I wanted something in my house, curated by me. When you cook something with your hands, there’s already so much love in it. When you put people around that... add a lot of warmth, play music, let people be themselves, you’re creating an environment that is very hard to come by.

I started doing the dinner parties around July 2023. I tested three a month, and I was nervous. I was shaking in my legs! I thought everything was going to go wrong. But you know what? They worked out fine. And, I got excellent feedback. That helped me get better and better and better.

So all of 2023, I was hosting test concepts through platforms like Airbnb Experiences, Dinner with Friends and I never had any social presence the entire time. I was doing everything behind the camera. You were experimenting and getting experience. I was very shy about showing my face and telling my story.

But 2024 came by, and that was when I thought, you know what, I need to put my face and a name to this. I went word searching for a bit. For some reason, I had the word “Bazaar” somewhere in my head. A bazaar is a spice market. We use this word a lot in India. There’s always someone saying, “Oh, I’m going to the bazaar to pick up stuff.” And so, I said, let’s go with that.

I created my first Instagram page in February 2024, and it had zero followers for a very long time. I was mostly taking pictures of scenes from the dinner table and of people at the dinner. I did that for a couple of months, and the page was very stagnant.

I used to post on Reddit, and people would flag me down and say, “You can’t promote your business.” I’ve had some dinner guests come from Reddit from seeing those posts. They thought it was a total scam, but they actually came and loved it.

Then I noticed: how would it be if I were actually to tell my own story in a 60-second format? And I was terrified of doing that because we’re all very judgmental about how we sound and look on camera, and cringe about our own voices.

I went through that whole phase for about 6 months. Beginning in February and all of 2024, I was experimenting with making content behind the scenes of my dinner parties, scenes, and nights of the dinners, and the page was slowly growing and reaching a very small audience, but not at the pace I wanted.

Here I was, thinking about how to spread the word in New York. I was under the assumption that if some publication discovers me, they’ll feature me in a newspaper, and that’s how the word spreads. I was reaching out to a lot of publications to see if they’d be interested in picking up the story. No one did.

Then I reached out to food content creators. So many of them... but didn’t hear back. One or two people said yes. I had my first creator come and recap her whole experience in New York around November 23 or 24, and that made a bit of noise, which was good and helped. That’s when I was like, “Oh shit, you know, like if you tell a story in a certain way, people will start observing your story.”

And I just didn’t know how to story tell the whole time. I was very uncomfortable. I tried to put my face out there even more. The more I did it, the more I noticed that people wanted to connect. People don’t want to connect with a tablecloth, a placemat, or a plate. I noticed a reaction from the audience: “Oh, she’s a real person behind the screen... so let me see what she has to say.” I kept building and tried content for a whole year, and it didn’t really stick.

But, enter 2025. April 2025 was when I made a scrappy video while I was having a really bad day (it was a bad anxiety attack), and I was trying everything to take my mind off of it....and just hit post on the video. You’re just powering through it, it’s wild! And that video was the one that went crazy overnight.

This reel was me explaining what happens when I convert my apartment into a restaurant. I invite 18 strangers in, cook all this food, and do it because I want to find out who I am outside of my nine-to-five. And that this is me challenging myself to build a life. There was a lot of audience resonance. And I’ve gotten hundreds of messages from people across the entire world saying, “This is me right now. I’m glad you’re taking this risk, and I want to do it too.” There was something emotional about the message that hit people. This is all of us on a regular day, thinking about all these things. We never say them. This was my first video that went viral. I was very lucky, and it doesn’t happen to everyone. I’m very thankful.

It feels like that was the universe’s biggest slap in my face, saying, “I am pushing you in this direction. Pursue it now. Go do it now.” The universe was literally, metamorphically, pushing me out and saying, “You’re done with that shit. Be yourself. Explore!” To me, that was the explosive overnight growth. I had maybe 2,000 followers, and the next morning I woke up to 10,000. It was crazy. Oh my god! What world does that happen in? Your world! Whoever is up there was pushing me in a different world, saying, “I’m putting you on this path. Now go do it.” And the fact that you answered and said, “Ok, I’ll do it.”

Something changed in my brain when that happened. I was like, there’s something here. I’m going to give it my all and keep pursuing that, sharing a lot more content.

Honestly, people love stories. People love seeing people figure things out in real time. They actually want to see someone going through the process. They don’t like anything where it’s just a beautiful aesthetic video. None of that matters.

I’ve tried making content of all kinds. I’ve tried making content with a very expensive camera and with my phone, which has a shitty, smudgy screen. The one that always works is telling a very, very authentic story from your own voice. And it’s genuinely something that you want to share and be a part of the conversation. Yes, and the more you talk about it: the things you’re uncomfortable about...people will find you real because we’re all uncomfortable to some degree at our core.

People don’t talk about it online because they don’t want to show the uncomfortable parts. Instagram is just a highlight reel. You don’t want to show the “non-highlights.” Why not? If anything, that’s the only real part of what’s left behind, so why not embrace it? I’m still figuring it out. I still feel like this whole world of being seen by so many eyes is fairly new to me. It happened less than a year ago, but I am so thankful that it happened and it came my way. It’s putting me on my path, and I have to give it my all to see what is out there for me. That’s why this last year was so instrumental.

I met so many people and made some solid friends through Bazaar. One of them was a guest from a dinner party in December 2024. She and I are very tight right now, and I would’ve never met these people if that didn’t happen. That is the power of female friendships.

As you evolve as a person, you meet people who are also feeling and going through the same. It’s just so beautiful to find people who are evolving as you go. I had to see that for myself to have a different perspective on life. Hopefully, it’s something that continues to last, because we were talking about this beforehand: we’re on a journey where we’re trying not necessarily to find ourselves, because we know who we are. It’s more about whether we answer “yes” or “no” to the path ahead.

It’s more about continuing to open the door for our inner child and our current selves to meet us where we are, in this older version of ourselves. And to genuinely connect back with ourselves, to then share that with our community.

What was last year [2025] like for you? What were a few highlights? I worked with some of my dream brand partners in 2025. My first dream brand partnership was with KitchenAid. Since I was 18, my dream has been to have a KitchenAid stand mixer in my kitchen. I was obsessed with that shit. I used to watch every cooking show, and they all had KitchenAids.

Fast forward to 2025: someone behind the screen saw me and said, “I want her to talk about KitchenAid.” Wow! That is, one of the biggest pieces of proof in my entire life. I started working on brand partnerships last year and earning revenue, which I didn’t know existed. I broke my first six figures with brand partnerships last year, which is insane. That’s amazing. Holy shit! That gave me so much confidence that, number one, the money aside, brands are even looking at you to say, “Let’s have Leslie tell our story. Let’s have Nirupa share our story.” It’s just so fun. And that was from June to the end of 2025.

I worked with a handful of brands, but KitchenAid was my first, and it’s my dream partnership. That to me is still like a pinch-me moment. And I worked with them twice. The second time was the recent dinner I hosted with them. That’s amazing. I remember, as a guest at that dinner, seeing how that partnership connected for you and the joy you got from being in that space. There was a full kitchen, and so you were truly physically able to “walk into” a dream partnership because it was a space that you could cook out of, that you could host people out of, and that wasn’t in your apartment, but a third space for you outside of your own. It became a third space for a community you already manifested and created, which is really, really cool to see. Absolutely. So that’s highlight number one.

Highlight number two was becoming my most confident self. There’s no way to measure this, but last year, a lot of people asked, “How are you so confident?” I am not an innately confident person at all. You also get confidence by action. Last year, I put myself out there so much, and it gave me so much back.

I grew a lot as a person last year as well. All this work I put into building a community led to a very close group of female friendships that have evolved, and I’ve matured with them. I’m very happy and hold them dear to my heart. And I am at my most confident version right now and it’ll keep getting better. That’s one of the biggest highlights that I could talk about that I can’t put a number behind.

Would you say the confidence came from proving to yourself that you can do it? Correct me if I’m wrong, but I feel like you’re competitive with yourself. You want to be the better version of yourself in any way possible. And it’s never been about,” I want to be better than this other person or this other thing.” You’re more like, “I know I’m good, but I’m not sure yet. But let me try, put some action behind it, and prove that hypothesis for myself. And if I can see it, it can happen.”

I’ve never said these words out loud, but that’s honestly the truth behind it. My life changed so quickly in such a short period of time that sometimes I have to take a minute to think, “Oh, wow... like all of that unfolded in less than 12 or 15 months.” There’s a lot of being prepared to receive luck in the world, but at the same time, you have to embrace it. Just go for it. I just did it, and I did it in a very messy way. In truth, that is the most real thing that I have said out loud in my entire life.

And you’re right, I’m a competitive person, and I get very competitive with myself. The sad part about it is that when you work in social media, you always see highlights. It’s very easy to feel like, “Am I doing enough?” You have to battle that fear every single day, and it’s not easy. You can choose to ignore it and focus on enjoying life. I want to document the process, and I’m going to work hard. I’m going to make money. I’m going to help people and build this container (community) in the process. Those are my goals.

I also want to enjoy myself and not feel like it’s a job. And... make money if I can. And build a really, really powerful community because I came from not having one, and I really want that. That’s my constant north star.

I love it. I see the vision, and I see it happening in real time for you right now. You and I sitting here came out of that north star and vision! Yes, because you and I put ourselves out there.

Bringing it back to what you said about being open and receiving luck, is that by being open to focusing on just doing the thing and letting it happen, it allows the universe to connect you to your path. I’ve personally always been very resistant, and lately it’s been about slowly unlocking it for myself. Let me do the thing, and if it happens, it happens. Great. If it doesn’t, it doesn’t, and that’s fine. But when it does happen, let me embrace it.

You’re a great example of being open to it. As much as you might not think you are, it’s actually manifested in so many great things so far and will continue to do so—which is a very hard thing for, maybe a blanket statement, but immigrants and children of immigrants to embrace, especially for those of us who have had parents who live really hard lives and try and give their children, like us, good experiences in the future.

Sometimes luck can seem scary because it doesn’t feel real. What I realized is that now, in our lives here, it’s up to us to decide which path we want to take. Because so much of our parents, our ancestors, and our families have given us to be able to arrive at this point...it’s now up to us to say, “Yes, I want to take this opportunity. Yes, I will receive this luck. Yes, I’m going to do this thing.”

To honor what and who has come before us, we also need to honor what’s ahead of us. I very much see that it’s in the path you’re on, and I hope for me too.

You’re already on it, girl! Sometimes it takes someone else to actually observe and say it because something you said was that you’re not trying to prove anything wrong. You’re trying to prove yourself. I never said that to myself, but seeing you actually put that in words, I’m realizing that’s probably what’s happening.

Confidence comes from action. But also, that nothing is truly out of reach for any of us. That’s another mental shift that I’ve had in my brain over the last year. I can sit here and have the most absurd dream and think it’s totally in my reach. Call that being delusional, but I’m just operating that way from last year. And when you operate that way, your brain gets rewired to look at the positives and look for opportunities in every little corner.

What are you most excited about in the next 3 to 6 months? One big tactical change is that I’m going to quit my job. I’m quitting my job! I’m going to keep saying it until my brain gets rewired. That’s going to happen. That’s going to be a big career change, working full-time in the creative space, which I have never, ever attempted. That’s going to be a big change. You’re already doing it half the time! Half the time.

I feel a lot more comfortable now that I’m doing a version of it, but now I get to do so much more. I’ll have all this time now to do all the things I just never had the time for, and to let my brain live creatively, fully.

I’ve always had thresholds to it, but now this is the year where I’m going to do some wild shit. You’ll see it unfold, but I’m going to do it this year, and starting with quitting my job. I don’t know where it’s going to take me, but it’s going to open a lot of doors for me to experiment, and who knows what’s going to come out of that? So many great things.

At the end of the day, why does doing what you’re doing matter to you? The decision that you’re making to focus on your creative career, the way you’re doing it? It’s important to me because, looking back, I was always a kid who wanted to pursue a creative path. But where I came from, I could never do it because I grew up in a family that didn’t have a lot of money.

I grew up in constant scarcity my whole life, and I really wanted to build a life for myself surrounded by abundance. It took a lot of hard work.

It took a lot of years of me busting my ass. And what does that lead me to? It leads me to creatively pursue this thing I’ve shut down for most of my life because I had to keep refilling my scarcity bucket. And now I’m filling up my abundance bucket. The time for scarcity is done.

Now I’m running towards abundance and building it. A big part of that is really bringing out the inner child in me, the one that always wanted to do creative shit that never had a chance to see the light of day. I am seeing myself more and more waking up and realizing that I want to do something I’ve never done before and go down that path because I want to see where it leads me. I’ve never fully had a chance to explore that, and now I’m going to do that. You are now, and that’s exciting! I’m going to do that, and I know that something I’ll get is meant for me.

This is the complete opposite of what I’m doing in my nine-to-five job. I’m good at the job, but it’s not something that I wake up looking forward to. And when you know that’s the case, I don’t want to be in that gray area for too long. And now that I’ve done some experiments and they’ve worked out fine, I’m going to take a full plunge.

Are there any common misconceptions about you or the work that you’re doing? Some of the content that I put out is obviously throwing dinners in my apartment. It’s a nice space, don’t get me wrong, but people who are out there watching my videos probably think, “Oh, she’s just probably rich, throwing dinners, and this is all she does.” The truth is, that’s not the case. I have a nine-to-five job that I wake up for and do my best every day. While I’m at it, I’m looking at how to build this creative life out there for me that fulfills me...the thing I’ve been trying to do for 30 years.

I’m a normal person living my life and entering a new era. At the same time, I’ve seen myself grow and change so much over the last three years.

As I’ve evolved, so have the people and relationships around me. I’ve found myself stepping into new friendships, and also naturally drifting from some that once felt like home. I’m learning that not everything is meant to come with you into every version of your life. And that’s not a bad thing, it’s just part of growing. Letting go of certain things hasn’t been easy. It’s something most of us go through at different points in our lives, but that doesn’t make it any less hard.

I’ve felt the weight of that over the past few years. It’s been challenging, uncomfortable, and at times, lonely. And when you feel like you’re not being chosen in certain moments, it can really stay with you. But going through all of this has made something very clear to me.

If you want a village, you have to be a villager. So I’m building myself into that. Through hosting, creating spaces, bringing people together, and treating people the way I want to be treated. And in doing that, I feel like I’m becoming a little better every single day.

I feel more deeply now than I ever have before. And for the first time, I’m actually allowing myself to express it.

Do you have any advice or something you’d share with a younger version of Nirupa? What would you tell her? This is something that’s very out there and not something I’m making up myself, but what I’ve learned in the last two years and with what I’ve experienced, is that done is better than being perfect. Go make it first, and then figure out how you can make it better later. Because the worst thing you can do to yourself is convince yourself that you will be ready one day.

Nobody is. Nobody will ever be. So when you put something out there, it’s going to automatically instill more and more confidence in you to keep pouring into it. For someone who is feeling trapped or someone who is feeling like, “oh, you know what, I want to make this change, but I don’t know how to...” I would say, go jump at it, and then you can figure out how to swim, which sounds a little scary, but that’s exactly what I did, and it has, if anything, transformed my life in the best way possible.

So my advice is: done is better than perfect, and just try.

Which Nirupa would have loved or hated to hear this advice? Every single version up until two years ago. But again, for me, it was like a major life moment that happened, which woke me up one day, and I said, “ What the fuck are you doing?” It takes that for some people. Some people, you know, it might never happen.

So my advice is don’t wait for that to happen. If you feel like you know it in your gut, trust your gut. By the way, your gut is 99% right. Trust your gut, and if you feel like something is not meant for you, it’s not meant for you. There’s another path.

Younger Nirupa didn’t know what she was doing. She didn’t know who she was. And it’s crazy because I grew up in an Indian household, and it was a very, very strict household. So, I never really understood life outside. I was a frog in a well. I had to build myself up when I came to the States. I had to understand how people talk, behave, and present themselves. How do I do a good job at work? All these things. I literally was reborn when I came here because I didn’t know what I was doing before that.

I was very sheltered in the household, where all they cared about was getting good grades: no social skills, none of that. I had to build all of that over time by observing other people. I feel very deeply, and I also observe a lot. Over time, that made me who I am, and it’s only going to get better.

Share a list of three things you’d like to recommend. You decide the topic.

1. Live alone by yourself. It teaches you a lot. It’s very easy to be around people all the time in a city like New York. You learn a lot about yourself when you are alone. It almost forces you to thrive and enjoy your alone time. That’s very important because we’re so good at having our brains occupied. Let yourself rest and reflect on the day. How do you make your space feel like home? How do you evolve in an environment that is yours? If you can live alone, it’s great. It’s the best thing.

2. Get a pet. I am a cat mom for two cats, and they have made me a better person. When you’re alone and living by yourself, and let’s say you had a bad night’s sleep... imagine you were waking up in a house of no pets. You wake up, and you’re like, “Oh fuck...” But with my cat, she’s sitting in front of my face, and automatically dopamine and serotonin, or whatever you call it, hit. It’s rewiring my brain the first thing in the morning, and you can’t start your day on a bad note. Get a pet; they bring out the best of you and your caregiving side. It’s done that for me, even though I was never a cat fan. I have a cat now, and I love love love coming home to her.

3. Take yourself on solo dates. A lot of people are very uncomfortable being alone, especially in New York. How funny is that? It’s a city filled with people, and you must assume that it’s easy to make friends. Go take yourself on dates. Go sit at a coffee shop, go to an old diner, and order a drink, observe people, strike up conversations. You’ll end up having a conversation or two that night. Who knows what comes out of that? That’s how you meet people and how you have conversations that will sometimes challenge the way you think. It’s very important to do that.

The most dangerous person on the entire planet is the one who assumes they are always correct. That their opinion is the right opinion. You need to go out there and meet people with different points of view. That’s what happens at the dinner table all the time and at the dinner parties [I’ve hosted].

I’m bringing 18 people with such diverse POVs and walks of life. I put them at a table together for six hours. One of the things I also do is shake them loose with a lot of deep questions. I love those spicy questions. And people love it when they can actually share something. That’s how it becomes a living and breathing table. I love seeing more and more of that throughout the night.

What song do you currently have on repeat?

Suddenly I see by KT Tunstall

Every single morning when I’m going to work, I play this song. It’s the opening song of The Devil Wears Prada, which is one of my favorite movies of all time. I have never been so excited for Devil Wears Prada 2! Miranda Priestly is such a badass. That’s if you can look past the facade she carries. She is an incredibly powerful woman, but she’s also human. That’s why her character resonates with me as well. And Anne Hathaway’s character...she comes into New York, figuring out her role where she wants to be a writer...when I came to New York, I was Anne Hathaway’s character. And I see myself evolving into Miranda over time.

I love that movie, and when you listen to the song, it’s just so uplifting. Listening to it first thing in the morning brings a fresh burst of energy every day when I get off the train for work. I play that song, and it’s like I’m living that life in New York. How lucky am I to be here?

As an immigrant, I watched that movie when I was maybe 14 years old, living in India on a small TV, and now I am living that life in New York.

Enjoyed the Conversation with Nirupa Konijeti? You can find her on Instagram @bazaar_nyc and on Substack @BazaarButter.

Nirupa is also passionate about giving back to World Central Kitchen

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Meet Kimmy Wu, a New-York based licensed psychotherapist and sex therapist, writer, and founder whose work centers on community and creating safer spaces for humans to live and exist in. As a third-culture kid raised between Taiwan and Florida, Kimmy shares how her upbringing shaped a lifelong awareness of emotional safety and the presence of being seen, held, and accepted. After beginning her career in hospitality and corporate marketing in Washington D.C., COVID-19 created an unexpected opening in her path, one that led her back to being in service of others through mental health care. This path led her to pursue her degree at Northwestern University and becoming a licensed psychotherapist and sex therapist helping individuals and couples navigate shame, sexuality, identity, and the work of becoming. Kimmy also explores the liminal space of becoming through her Substack, Between Living and Dreaming, blending personal reflection with cultural critique. She is also the founder of Thirdspace, a platform designed to help people build real, emotionally grounded relationships in an increasingly disconnected world. Across therapy, writing, speaking, and technology, Kimmy’s work is unified by a commitment to care, autonomy, and the belief that safer worlds are built through intentional connection.

Interviewed in August 2025. | Conversation has been edited for clarity and brevity. | Also heads up, there’s some explicit language in this conversation.

Please introduce yourself. My name is Kimmy. I’m just a girl with a wide range of ambitions who wants to help make the world a better, safer place in many ways. Safety is one of those concepts that I often think about, as a woman, in all kinds of contexts we find ourselves in. It’s important to understand that the world is a dangerous place, and the only thing we can truly do is try to create safer spaces for others.

Professionally, I’m a mental health therapist. I specialize in working in sex therapy, but also do trauma work and help folks with all kinds of backgrounds and struggles. Specifically, I love working with people on identity formation, learning about their pasts, and how that past informs who they are today. And dreaming about who they want to become.

I also write about this liminal space of becoming in my own Substack newsletter, Between Living and Dreaming. That’s a passion project that I hold very dearly. Although the intent was to write about that liminal space, I’ve also slowly found myself incorporating cultural commentary into my writing, discussing the things I notice in my work and as a human being navigating the modern world. For example, sharing some of my own critique about how we need to resist the urge to make things easier, even though, yes, of course, I wish people’s lives were easier

Before becoming a mental health therapist, you had a background in corporate marketing and hospitality. You also grew up in Taiwan and immigrated to the United States at a very young age. Were there any moments in your past lives that were important in shaping who you are now, if at all, especially to your passion around safety? I really appreciate this question. I’ll start from the beginning: I was born and raised in Taiwan, and I moved to the U.S. when I was about 13 or 14.

My observations of safety started when I immigrated, but it was always present, even when I was in Taiwan. Not to flatten the narrative of this being the immigrant experience, but my parents were immigrants. I’m a third-culture kid. My parents moved to Taiwan from Hong Kong, and they’ve been there for 30-40 years to this day. My dad still speaks Mandarin with a slight Cantonese accent.

Even though I was born and raised in Taiwan and very much identify as a Taiwanese person, I knew there was always discrimination towards my parents as immigrants in their workplace, even though they are not a visible minority. That brought on a hyperawareness about what being different meant, and it wasn’t always safe to be different.

From my own experience as an immigrant, I don’t want to say people were malicious or mean to me in any particular way. Teenagers in general can be bullies. There’s a naivety that I didn’t think about. Not that I didn’t think about what safety meant at that time, but it’s more of where I didn’t really know how to define what safety was like. I wanted to be with people all the time. And to this day, I still feel that, but a lot of it came from insecurity about not knowing where I belonged. There was a deep yearning to be known, held, and accepted. To me, that is what safety is. Of course, there are more basic levels of security and safety. This is your own experience. Exactly, and for lack of better words, the definition of safety for me at that time was as a teenager.

So when I say safety, what I really mean is more than just the obvious. I don’t want violence to happen to us. It’s also the emotional safety that is just as important, but folks don’t necessarily think about it as much.

Between Living & Dreaming

When "Safe" Feels Boring: Reconciling Security with Desire

“I’ve finally found someone who makes me feel safe,” they say. “He’s kind, he listens, I don’t feel like I have to shrink, perform, or chase…

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10 months ago · 9 likes · Kimmy Wu

When you immigrated from Taiwan to Florida, did you come on your own? I moved to Naples, Florida, to live with my aunt and uncle. My dad stayed in Taiwan, and he never moved to the U.S. My mom would be the one who came to Florida for six months at a time and went back.

This is something I really appreciate, especially now as an adult, looking back at how much she had to give up for me and my brother to be here six months at a time. And having a new perspective on what that must have been like for someone who really takes my career seriously. I can imagine it wasn’t easy for my mom to decide to give up her career as a physician to become essentially a stay-at-home mom when she was in between two countries, and suddenly, my dad became the sole breadwinner of the home. I hadn’t really thought about how much pressure that must have been for my parents until I was more mature.

There’s a weird dilemma: I wish my parents had shared with me the ways they struggled, but at the same time, I’m grateful that they never really put that pressure on my brother and me. I grew up quite blissfully unaware of the ways my parents struggled, but at the same time, there’s also a lot of mixed messaging that made things very confusing.

For example, if I ever wanted to learn something, my parents would not think twice about paying for lessons or allowing me to pursue any interest. But then, if I wanted something nice, my parents would be like, “Nope, you can’t have that.”

It definitely shaped my value system in many ways. Not that I don’t like nice things, but I absolutely value the education and all the interests that I’ve pursued throughout my life. That’s what I hope to pass on to my children as well.

I’m reminded that my parents were also similar in that, if it were for education, they wouldn’t hesitate to pay for it. My mother was also big on life experiences, and, with limited funds, we would take Chinatown bus tours that brought us to many places, in the safety and familiarity of a Chinese tour guide and guests. It was all about how we could make this work even without the frills, because my parents valued life experiences, and that has also really shaped my values.

As someone who is a pleasure activist and a sex therapist, I very much believe in human freedom to indulge when it’s necessary and also when it’s appropriate. Hopefully, I’ll have the means to buy both experiences and sometimes frivolous things for my children in the future, of course, within reason.

Moving forward in your timeline, how did we arrive at pursuing hospitality and therapy from when you first immigrated to the U.S.? I realized I’ve never identified as a “doer,” but looking back, anything I ever said I was going to do, I actually accomplished. Becoming a therapist is one of them.

In terms of my timeline, I ended up going to college in Orlando at Central Florida. I loved my time there. It was really fun, but I definitely could have taken my academics more seriously. College was the first time I got a taste of what freedom was like—making my own decisions and coming into who I wanted to be, or at least having the space to really think about it. I started off as a pre-med student because I thought wanted to become a doctor, like my parents. I realized organic chemistry was going to be the bane of my existence. And it was. It’s the class that weeds most people out, and I was like, “Nope, I don’t think this is for me.”

Then I just started to go to different lectures on campus, wherever the professors allowed it. I stumbled upon a hospitality class. There’s a warmth in the way [the professor] presented the ethos of hospitality. And as someone who likes to take care of others, that really stood out to me, and I started doing my own inventory of, why did I even want to be a doctor in the first place? Some of those reasons included wanting to be with people, to work with people, and to serve people. There are definitely certain ideals that carried through, even as I decided to then go into business and the hospitality industry.

And I remember, after a semester or two of being a hospitality student, I recall having second thoughts. I was like, “Oh my god, am I making the worst decision of my life, giving up medicine to come into this?” It’s a hard decision, and it would mean a very different kind of life and tax bracket. Real. Yep, and I remember there was a moment where my mom actually was like, “Well, you have to think about this. People like ‘us’, aka doctors, also need vacations. So when you do your job well, and specifically, being in the hotel industry, then that’ll help [doctors] do our jobs better. That’s the moment I was like, “Yeah! Crap, are you my mom?! Like, who are you?”

My mom has nuggets of wisdom that sometimes really surprised me because I love my mom to death, but she sometimes can be quite critical of me. But that was one of the very positive moments that remind me how much she cares—though I’m not even sure if she even remembers that conversation. To me, that was a pivotal and radically self-accepting moment, one in which I felt she gave me permission to have.

And so, I kept pursuing it and ended up having a career in the business of hospitality. However, a few years into my career, COVID hit, and all my hotels were shutting down. While that was happening, I was also confronted by a moment of realization that something felt missing. I came into this career with a lot of interest and curiosity, but I realized that I’m not a good fit for the corporate culture and lifestyle. There are many moments when I feel unsatisfied, like a tiny screw in this big machine.

And not to knock anyone who wants that, because there’s a level of stability and safety that I definitely miss now, as an entrepreneur. But at the same time, there weren’t the kinds of opportunities I wanted to learn more and do more that were freely given to me. Was it also the way you were learning and how you liked to do things was different from what corporate culture was affording you? Yeah. Exactly. And that’s why, when COVID all of a sudden hit and hotels and trips started shutting down, it was really stressful because I was waiting for news of being fired or furloughed. I really appreciated my team and company for doing everything they could at the time to keep me on board for as long as possible, but it was actually a very clarifying moment for me when I was furloughed because despite the financial stress of paying rent in DC, I felt a sense of relief. That felt like an opening for new possibilities and potential. That relief definitely grew over time. As soon as I started coming out of the phase of panic and not really knowing what’s next, I started taking a break for myself.

When you’re in a corporate culture, you’re chugging along. You’re doing everything you can to prove to your bosses that you deserve more opportunities and whatnot. But that was the first time in a long time that I gave myself time and space to read all the books I wanted. And to take care of myself and my body.

Several things have happened since then. I started thinking, obviously, about what I want to do next. Do I really want to stay in this work environment, or is there something else I can do? There’s a part of me considering even business school because, in undergrad, I was intrigued by entrepreneurship.

That’s when I figured maybe I should try opportunities that allowed for more creativity. I started looking into nonprofit marketing, and ended up getting a job at the National Register of Health Service Psychologists, an organization that supports health service psychologists through membership with benefits.

That was one of the stepping stones. And what ended up happening was that I realized I was reading a lot of books that were written by therapists, which I didn’t really register at the time. I was heavily invested in my personal development at that time, and I really wanted to find my own therapist—but I could not find an Asian therapist who was taking new clients or available in my area.

And then I had a life-altering conversation with a friend where he shared all the very tough things he was struggling with at the time. I listened and provided support in the best ways that I could. And, at the end of the call, he said, “I don’t know if you’re going to take me seriously, but I think you should consider being a therapist. I know you’re looking for a new career, and I think you could potentially be a really good fit for that.” And I immediately shut it down because I think there was a part of me that’s like, “Well, I left the medical field to pursue something else, why am I going back to that?”

Another reason was that I didn’t want to go back to school for seven or eight years. I thought I had to get a doctorate degree. I had this misconception that I also had to be fully perfect. I have my own perfectionistic stuff that I’m still working on. I was like, “I’m not stable enough to be a therapist.”

A few weeks went by, and I really could not shake the thought. That’s when you know it’s real. And potentially a really good idea! And that’s when I was like, let me do my due diligence and some research. I decided to start volunteering for the Crisis Text Line because there was so much demand during COVID, and that felt really meaningful. I wasn’t getting paid, and I was feeling really fulfilled. So, maybe there’s something here. Not that I ever doubted my friend, but again, he’s a jokester, so I didn’t really take his suggestion seriously initially.

So then, that’s when I decided I’ll apply to school and we’ll see what happens. If I get in, then great, I’ll do it. I’ll take it as a sign. If not, then I’m just back to where I was anyway, and it’s not a big deal.

I ended up getting into two out of three schools I applied to. That’s incredible! I ultimately chose Northwestern, and I have no regrets. It’s a very rigorous program, and it really prepared me academically and clinically in ways that made me feel very secure going into my practice.

What stands out is that you took an idea and gained more information through smaller achievable tasks to help you make a firmer decision without overwhelming yourself. And each decision helped answer or dispel any assumptions. Yes, there were a lot of actions being taken, and it’s part of the doer identity that I’m slowly identifying in myself. There’s a part of me that needs to make informed decisions. I sometimes like to allow life to happen to me, but in reality, there’s a lot of thoughtfulness to try to put into all the decisions I make in my life. And that’s what living intentionally really means to me.

The rest was history. I graduated from Northwestern and decided to leave DC. It was very bittersweet, but I pursued my dream of living in New York City. Now I’m here, sometimes thriving, sometimes struggling, and meeting a lot of amazing people like you. And really genuinely loving my life. That’s amazing.

Could you explain to folks who may not be as familiar with therapy what a psychotherapist does, and also what a sex therapist does? A psychotherapist is someone who practices talk therapy. We could be broken down into counselors, LMFTs (Licensed Marriage and Family Therapists), or social workers, and most likely have a Master’s. Psychologists have a doctorate degree, and they are also therapists. So I’m a counselor because of the degree I received.

Psychotherapists work with a plethora of different issues. People usually find their own niches within that, but sex therapy is much more niche.

For sex therapy, we only do talk therapy. That’s the part I think people often are like, “What does a sex therapist do?” They also wonder if a sex therapist gets physical with their clients or anything like that. And the answer is no, it’s strictly professional and talking only.

To become a sex therapist, there’s a lot of specialized training and certifications that you have to go through. The certification part is not required, but there are specific training programs that you don’t get in regular grad school. So it’s in addition to what you’re doing.

Why did you choose to pursue sex therapy? Personally, I think sexuality is one of those topics that we don’t really talk about, but we really should. That’s my personal opinion. I can’t pinpoint a specific moment when I decided to be a niche sex therapist. Throughout my career, I’ve always been very curious about the topics of sex.

For some context, I come from a religious family, so it was a pretty sex negative space, which is ironic because my mom’s an OB/GYN. It was always like, “no sex until you’re married” kind of thing. I realized, personally, I had a lot of shame around sexuality and a lot of misconceptions throughout my life that informed my curiosity. My mom says certain things, the church says certain things, but I don’t know that I believe in that.

I am also someone who likes to do things that other people don’t want to do or haven’t done yet. It’s not about being original; if no one else is doing it, I’ll do it. Pursuing sex therapy was kind of the same, knowing that sexuality is such a taboo, along with mental health being a taboo in the AAPI community. And so, I decided that’s where I need to go.

I don’t want to lump Asian or Asian American culture in one, but I do know that discussing sex or the topic of it isn’t openly taught. Maybe we’re similar, but what I’m picking up is that you and I both like to have more information, and thus we want to ask questions to learn more. Because there is freedom in having this level of epistemic curiosity to be able to form my own thoughts, opinions, values, and principles. Other people are telling us, and we’re just taking the word as it is, like, “oh, I’m supposed to do this now,” but, innately, for you and me, we’re like, “no wait, I want to understand more as to why.” And then I want to make my own decisions and form my own point of view.

Now that it’s been a couple of years into your career as a therapist, have there been any interesting surprises or any lessons you’ve been learning along the way? Where do I begin! There are so many layers to this.

I have learned so much about myself through this work in reflecting on my clients and how my way of interacting with them has shown me who I am in different kinds of contexts. It’s shown me my own limitations as a human being, which is extremely humbling and freeing at the same time. And my capacity for love and for care, and also this undying tenacity with me to want to bring more freedom and love to the world.

This is also a part of why I think sex therapy is a big piece of activism I care deeply about. There’s a lot of freedom, historically, in the way we fought for sexual freedom that is both political and personal. And as someone who is a radicalized healer, I would say, this is one of those spaces that isn’t just a personal thing. Sexuality is connected to our bodies, and our bodies are now under attack by the current administration and by many of the social systems we live under. Something that I learned about myself is that I will not rest until change happens or until I feel like I’ve done enough to contribute to a safer and freer world for the next generation. That’s a big part of why I do the things that I do.

Then there’s the interpersonal piece: being able to really connect with these amazing humans who sit in front of me week after week to talk about some of the most difficult and most beautiful moments in their lives. It’s such a privilege.

We started this conversation about what humanity is, and I witness it every day. I don’t want to give a specific definition of what humanity is, but we are human, and there’s something really beautiful about that. To be two humans facing each other and seeing each other in that.

From the therapy side, that’s very one-on-one interactions. I have personally witnessed you as a speaker at two forums: as a moderator for Dr. Stacey Litam’s book launch and as a speaker at the Asian American Film Festival’s conversation on “The Mind Behind the Lens - Navigating Mental Health in Creative Fields.” And from our own conversations, I know you want to continue to do more speaking engagements. What are your hopes or goals for expanding through speaking engagements? And, what have these engagements taught you? It’s been an ever-evolving thing for me to try to understand what my message is to the world. There are so many that I could touch on. As someone who just started writing publicly, I’m realizing that the kind of information I want to share with the world is about empowerment for personal autonomy. And not allowing systems to control and oppress. In many ways, that touches on the work of moderating for one of my mentors (Dr. Stacey Litam) and her book, and on advocating for the framework she’s developed and the intergenerational healing she stands for.

And on top of that, working with the film festival was really particularly meaningful in supporting other AAPI storytellers who also have their own messages that they want to share with the world. At the end of the day, they’re the biggest realization that I am just one of many voices. I can both hold importance and dignity in the words that I share and, at the same time, realize that there are so many people out there trying to do the same. There’s something just really beautiful about that nuance. And, as I get to know more people in the film industry, I am realizing that storytelling is an important part of humanity.

As someone who practices narrative therapy, I believe in writing our own stories and endings that are not doomed to fail from the beginning. There’s a freedom in deciding that even though I know I’m figuring out and have certain patterns, we’re not doomed to keep repeating them.

I actually wrote a song about that, and it's a little bit of an acknowledgement to my own trauma in the past and how that's informed different kinds of patterns in my life. But there's a very hopeful ending that alludes to this self-choosing and radical self-acceptance, which allows me to really step into my own power and make different decisions that go against the grain. That has also allowed me to meet other people who have been supportive and holding me when I feel it's difficult to go against my own brain in my own personal healing, which makes me feel really safe and really loved. That's a lot of positivity in the message of, “you get to write your own story, and we're not doomed.” We don't have to be.

A phrase that keeps coming to mind is that you want to be “part of the conversation.” That, and you are finding ways to be an active participant in conversation. Because everyone can chime in on something, but it’s about how you do it with a lot of intentionality that can help touch another person. That, and they can do the same for you. Whether that is in your one-on-one therapy sessions, the talks, or writing for your Substack.

In addition to speaking and writing, you’re also a startup founder, right? Yes, and all that I do is very much connected.

My startup started as a random idea where I woke up one day last fall and was like, “What if I built an app to help people learn how to be more empathetic towards each other?” Because there are so many ways that we are so focused on our own needs and egocentric ways of being, especially in modern society. We’re so focused on our own survival that we forget about other people and forget to witness other people’s humanity and their struggles.

The idea started snowballing into my startup, called Thirdspace. It’s not a literal space, but hopefully becomes a tool that helps us learn to connect better with each other. The premise is that it’s meant to be an AI companion/guide that enables you to reflect a little more on your relational patterns, and to be scaffolding for the ways we can show up for each other.

I want to preface by saying that [Thirdspace] is not meant to replace therapy in any way. It’s a tool that helps you connect with yourself and, in turn, connect better with other people. I’m building a curriculum for some skills development, and the framework I created focuses on community roles.

Between Living & Dreaming

Building Thirdspace: A Founder's Manifesto

TL;DR: We’re more connected than ever, but lonelier than we’ve ever been. I built ThirdSpace to help us remember how to be with each other—starting with how we show up in community…

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10 months ago · 5 likes · Kimmy Wu

We talk about belonging in such an egocentric way: “How do I belong?” Or, “how do I get other people to accept me?” Which is important, but something that came to me in the past few months is,” Why don’t we ever talk about what roles we take up in community?” Some people are naturally better at noticing others’ needs and therefore at caring for them. These are the caretakers. Then there are some people who are natural leaders and are unafraid to say, “Hey, I noticed we’re a little stagnant. Here are some of the things we can do right now.” Then, certain visionaries are incredible at seeing what’s possible. These are just a few examples.

I started mapping out [the framework] based on the people I know. I explored which qualities help them shine in the community. I created 12 roles, and that will inform the framework and what Thirdspace will be doing.

It’s not meant to be a regular personality assessment where you take it once and never think about it ever again. You use it, talk about it, and then connect theory to practice. Now that we know this is what makes us who we are, how do we operationalize this information? We’ve spoken about Thirdspace before, and in addition to the framework, it’s also not meant to be rigid. Exactly, it’s dynamic. You might identify with one role, but in different context and seasonality in life, you can become something else as well. It doesn’t mean you’re only one or the other.

At the end of the day, why is all that you’re doing important to you? It’s important to me because I genuinely want people to live more connected lives. I love people and humans. As someone who has seen a lot and dealt with a lot, I have never ever gotten to a place where I was ready to give up on humanity. There’s a part of me that radically loves humans and our capacity to love and be with each other.

Now that I’m saying that out loud, there’s definitely a part of me that knew what it was like to not understand what belonging felt like, and that deeply lonely yearning part of me wants to make sure that other people don’t have to experience that if I can help it.

As a therapist, there’s one-on-one support. The startup [Thirdspace] is more about finding a scalable way to deliver greater impact than I can as an individual. Writing and speaking engagements are also the same—just really hoping that people know that there are people out there working actively to make the world a safer and better place for everybody. Selfishly, I want to build a world where hopefully my future children can also safely belong.

That’s very hard to do, but incredible to do it and keep pushing on everything you’re doing. It’s very clear to me that, throughout my life, I’ve started thinking more about why I do the things I do. There’s a huge part of me that’s really big on wanting to contribute to the world so that the next generation can live better lives than we do. Maybe it’s because I watched a lot of Naruto growing up! Laughing

Are there any common misconceptions about you or the industry you’re in that you’d like to dispel? I’ve definitely thought about this before and never really tried to confirm with anybody if that’s an actual misconception or something I made up in my mind.

I have a tough exterior, at least I think I do. As women, we’ve had to survive so much. And as an immigrant, there are so many parts of my story that made it so that I had to be very independent, strong, and tough in my own ways.

But, there’s also an incredibly gentle and tender part of me that doesn’t always get shown as easily. I wouldn’t say I’m not vulnerable, but my vulnerability has always seemed prickly because, again, it has its own built-in protective mechanism. So, maybe a misconception is that I’m just a tough person, which is so contradictory to the softness that I try to bring into my therapeutic work.

Totally, and earlier today, we had chatted about wanting to be in our “soft girl era.” There’s a perception of who you are and then what people perceive you as. You know who you are deep down, and it’s like, how do I help others see that version of me as well? It’s not required, but it’s nice that you know that about yourself and can share it with others.

I don’t see you as someone with a hard exterior; instead, you’re really passionate about what you care about and want for the world. Some people think that’s very scary because they don’t know how to do that themselves. Oftentimes, especially if the perception of an Asian woman is that we’re supposed to be soft and submissive, the moment we have an opinion or point of view, it breaks a sort of mental model people might have about us. And we often operate on a spectrum where people can only understand if you’re “this” or “that”, not maybe somewhere in between or both.

And finally, do you have any advice for a younger version of you? If there’s one thing, it would be to let a younger version of me know how loved she is. Like how deeply loved and cared for she was. I’m getting emotional when I think about that.

There’s an existential loneliness I’ve carried throughout my life that’s been so overwhelming. As humans, we’re born alone and we die alone. There’s something really scary about that to me, but it’s also something natural.

There are so many micro moments in my life when I thought I had to be really perfect to be accepted, loved, and cared for, when in reality that was already given and true. But I didn’t really know how to accept it or how to even see it. I don’t blame her. That’s the kind of environment she was in. That’s how I reacted to the world and the people around me,, but there’s a part of me that recognizes that I was really, really loved.

To this day, there’s still a tiny part of me that feels like I have to earn love, belonging, and care that probably will forever be there. But there’s also been a lot of healing over the years, where I’ve learned to love myself in ways I didn’t before. That level of permission we give ourselves and the space to choose to react differently to the parts of us are critical. Not that I would wish my life had happened differently, but I wish I had realized sooner.

Would you tell your younger self she is loved? Yeah, she is so loved and exquisite.

I’m planning a podcast called “Exquisitely Human” right now. It’s a term that my therapist gifted me. She would say, “Well, Kimmy, that’s just exquisite.” It just really stuck with me since. It’s like making space for not just the black and white but everything that goes in between.

Thank you for sharing that. I love this question in particular because, especially for folks in this later stage of life, they’re often asked about their life experiences, but in reality, we’re still learning. All I know is what I experienced before, and it’s lovely to take a moment to think back for ourselves because there’s a lot of life ahead of us, but there’s also a lot of life that was lived before. How do we still love ourselves as we continue moving forward? Because it’s not a new journey each time, we’re building on our current one. Exactly, there’s so much wisdom in taking inventory of all those moments that we’ve survived and lived.

What’s a song you currently have on repeat?

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This was a song I knew as a teenager. There’s something about lyrics in Chinese or Taiwanese pop songs from the past that has this whole narrative and something very lyrical and poetic. There’s so much meaning in every word.

The core of this song says,” I want to hold you, and I’m also fearful of letting you see the tear that’s about to fall.” It’s very emotional, and it’s a really pretty song.

What are three things you’re really enjoying right now that you want to share with other people?

1. Traveling. I recently went on a trip with our friends, Alfred and Justin, and it was freaking amazing, which I wrote about in my newsletter. There’s something deeply nourishing when you’re in a foreign country or city, just a place you’re so unfamiliar with, and it can be both uncomfortable and extremely revealing. The first thing I do when I get somewhere is always ground myself with a cup of coffee.

2. Reach out to a friend. Reach out to somebody, even if you are not good friends yet. I’m all about leaning into your curiosity in life, whether it’s a random topic you’re passionate about or a friendly person you know, like an acquaintance. Then find out what it is that they are really about. That’s something I wish more people did. Looking at the relational landscape, not just the romantic one: we’re so in our own world sometimes. There’s something really nice about having the technology to reach out to anyone and DM them about what they do. Or even learn a little more about them and show that, “hey, I know we’re not close, but I’m thinking of you and wanted you to know that I see you.” Some of my best friendships only happened because I was like, “I don’t know you, you seem pretty cool... can we hang out?” And that’s how it all happened. Then, of course, there’s the follow-through piece. And that’s the doer. You have to keep reaching out, keep hanging out to really build a relationship. Often, I notice you only see people in specific contexts, such as parties or group hangs. But friendships are multifaceted. If you only see someone at a party, that’s your party friend, but that’s not your friend who, when shit hits the fan, is there for you. Are they going to walk your dog for you if you can’t make it home? Part of it for me is about resisting a lonelier world, and we’re all culprits of breeding that kind of dynamic.

3. A repair after a rupture can be very powerful. For example, I was recently in a dating “rupture,” which is a strong word. He used the word “friend,” and I was really heartbroken by that. After going no-contact for a while, we had a conversation that was initially difficult and frustrating until I finally shared my worries and struggles in my personal life that he didn’t have context on. The vulnerability allowed both of us to soften and realize, “Oh damn, it’s not me versus you.” We started the conversation fighting for ourselves, and eventually we were able to face the thing together. It showed me that I have the ability and capacity to fix things between us. This is also important in friendships. Any ruptures we don’t attempt to repair are lost opportunities for more connection. And in many ways, this is both the part of me that loves deeply and part of me that knows how lonely life can be.

There are so many people in the world, and yet we’re sitting next to each other. To me, that’s not a coincidence. That’s a miracle and I want to treat the relationship as that. There’s so much dignity, love, and respect that I have for people who I get to orbit around and who I allow in my life. There’s a seriousness that I wish people could see. It’s not “if you don’t work out, I’ll find someone else.” In so many ways, modern society has taught us that we’re expendable to each other. My interpretation of what you’re saying is that it’s important to try together. Yes, whether in romantic, friendship, or family. There’s a lot of value in trying.

Enjoyed the Conversation with Kimmy Wu? You can find her at www.kimmywu.com, @asiansextherapist on Instagram, and on Substack, Between Living and Dreaming.

Kimmy Wu is also passionate about giving back the American Civil Liberties Union (ACLU) because, in her words, “fuck ICE and fuck this administration. No amount of therapy can fix human rights violations. We need system reform.”

The ACLU’s mission is to create a more perfect union — beyond one person, party, or side. And to realize this promise of the United States Constitution for all and expand the reach of its guarantees. As part of this Conversation, a donation was made to the ACLU.

You can support the ACLU by donating directly.

west & ease is part of & luo studio, where I do fractional design consulting, design coaching, and host creative community events. If you’re a brand, team, or creative partner interested in collaborating, I’d love to connect. You can learn more and reach out at andluo.studio.

Interviewed in May 2025. This conversation has been edited for clarity and brevity.

west & ease is a space for conversations with creatives, insights on design, and the moments that bring community to life. I’m Leslie Luo and in this conversation, I’m catching up with Sam Ray Lee—a creative and part of the Brooklyn-based music collective Umami House.

We first spoke in 2023. Since then, a lot has happened. In this recent conversation, Sam reflects on what he’s been building over the past year and a half — from learning how to create the right atmosphere for live music, to finding that sweet spot where energy, space, and sound all come together. But it wasn’t until he came up with the idea for Jam Battle, a one-v-one musical improv showdown featuring talented artists, that he saw the full potential of what this could become.

Also heads up, there’s some explicit language in this conversation.

To learn more about Sam and his work, you can follow him on Instagram @raytheidea, @umamihousemusic, and @jambattleofficial.

You can also read our first conversation where Sam shares more about his creative journey in 2023.

west & ease

Sam Ray Lee on how creativity can be a full-circle journey

Meet Sam Ray Lee, a musician, singer, songwriter, UI/UX designer, freelance photographer, and one-half of the musical duo Umami House based in Brooklyn, NY. Sam's creative journey starts from an early age. It morphs into an integral part of his identity, with each new pursuit growing and adapting to particular periods …

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2 years ago · 3 likes · Leslie Luo

west & ease is part of & luo studio, where I do fractional design consulting, design coaching, and host creative community events. If you’re a brand, team, or creative partner interested in collaborating, I’d love to connect. You can learn more and reach out at andluo.studio.

Credits

Intro and outro song: Friends by Umami House

Umami House’s first song, Move Along

Audio from the first Umami House Experience recap

Audio from the second Umami House Experience recap

Audio from Umami House x 12 Pell collaboration

Audio from Umami House Presents Jam Battle 1 recap

Meet Ka Yee Chan, a Hong Kong-born, Brooklyn-based maker and third-culture kid whose creative journey is rooted in curiosity, care, and community. What began as childhood art classes grew into a lifelong exploration of thoughtful design and accessible creativity. While her path from coffee shops and plant stores to hospitality and events may appear nonlinear, it reflects a deep commitment to aligning her passions with her daily life. Over time, Ka Yee found her voice in event production, where logistics meet genuine human connection. Whether she's shaping clay, curating experiences, or designing community spaces, her work centers on bringing people together. At the heart of it all is a long-term vision to build a retreat upstate where people can slow down, make, and reconnect with themselves and with one another. Ka Yee reminds us that growth doesn't have to look conventional; growing differently is still growing.

Interviewed in May 2025 | This conversation has been edited for clarity and brevity.

Please introduce yourself. My name is Ka Yee, not "Ka." My first name is two words, and a lot of people get that wrong. I'm a third-culture kid. I was born in Hong Kong but came to America when I was nine and was raised in Brooklyn.

I've always been a maker, and I love creating things. Currently, I'm an event coordinator producing cultural events.

How did you become a maker? My journey to becoming a maker began when I was nine, after moving to America. I became very shy since I didn't know the language, even though I was the same noisy kid from Hong Kong.

I learned to speak English in Hong Kong, which has given me a distinct accent and a unique way of speaking. And so, kids would laugh at me. They weren't being malicious, but it made me hesitant to talk because I didn't want to get made fun of.

My elementary school teacher introduced me to art, which became my escape as I looked forward to creating art every day. I realized I had a talent for drawing and crafting. That same teacher later recommended that I apply to a junior high school with an art specialization. Later on, I also applied to an art high school. And that's where it all started.

Do you think art is a way for you to connect with the community around you, or has it always been a solo activity? Both. I enjoy it as a solo activity because I appreciate having time to think through the process alone. It was definitely a solo activity when I was a kid because I was trying to escape from my new environment, where I had an official reason not to talk to the other kids. As I'm older, art has become more of a community thing. I enjoy sharing what I do and collaborating with others to create things.

It's incredible to see how it's transformed and to see how you've integrated art into your day-to-day life. I personally never attended an art school — what was that like? Were you into specific types of art, and was there anything that shocked you about the experience along the way? That was also my first experience when I was in junior high school. I didn't know what to expect. I didn't think much about what was taught, as art was just one of the classes offered. However, that changed when I entered high school. Everyone was so talented in their own way because that particular art high school had students who were focused on art specializations.

I realized more of what I lean towards in high school: 3D and sculptural work the most. I love collages. Painting is not my strong suit.

Most of the time, I have a big picture of what I want to achieve. Then, I will start making it and will have a plan. Over time, I began to enjoy the process without worrying about the outcome. That's why I never call myself an "artist"; I don't think my brain thinks like an artist. I really like to design things. I love making things functional, even if they're a bit funky. And I usually have an end product in my head and find creative ways to take it all together.

What's your definition of an artist versus a maker? I'm unsure if I have a definition for it, but I feel cringey about describing myself as an artist. Artists are also a way of life, influencing how they think and live. It's not about producing a certain "thing." When I studied design, we often talked about function and form. Aesthetics is part of design, but it is almost secondary because the design needs to serve a purpose. Is there a problem that it solves?

I like to call myself a maker because my mind is more like a designer's mind than an artist's. To me, artists figure it out as they are in the process because there isn't an "end product." They have a vision of what they're trying to create, but it's not like one product they're trying to make functional. It's almost like their diary: a form of expression.

The word that keeps coming to mind when we speak is "moldable." Is the way you create by molding something? For example, the 3D work you do, such as ceramics, and even the present day, where you curate and host events and workshops—these are all formats where you're molding something towards a functional vision rather than having it be the canvas itself. Would you say this is how you approach being a maker or some of your work?

It may be similar to my personality, as I'm not one to express or let out my feelings. I visualize a painter with a canvas expressing themselves. That's not me; I don't think that's what you need. That's not my personality. My personality is more about play and form. Everything has a step, but I'm not strict about it. There's a process in my mind that I need to do first, so I'm going to do that. And do I have enough time to do all of this together?

For example, when creating ceramics, I realize I'm impatient because I don't have enough patience for hand-building [technique] versus the wheel. The wheel begins with a structure, and you continue from there. Once you finish the clay, you're done.

What about tools? Personally, I don't like to use a lot of tools. My art practice is pretty straightforward and simple. I feel art should be accessible. I share similar views on accessibility. One of the main reasons I dislike being categorized is that I wonder what would have happened if the teacher hadn't asked me to join the art club without seeing any talent. Then, I would never have been in it. I believe everyone should have the chance to express their creativity, whether it's creating a collage with a magazine or crafting a small air-dry clay sculpture. You don't have to be an "artist" to do crafts.

In previous conversations, we've chatted about how you started building your community in New York many years ago. Could you share how you started? For the longest time, I never really knew what I wanted to do. When I was in high school, I wanted to be a fashion designer, so I studied fashion in college. But then I realized I'm not that passionate about fashion. I love clothes and the construction of them, but I wasn't as enthusiastic as other students about this designer or that designer. What's trendy? I don't know and don't think I am interested.

That's when I realized that what I thought I would be was not really what I wanted to be. Even after I graduated from college, I didn't work in the fashion industry. I did a freelancing gig, and I really did not enjoy working there. From then on, I started eliminating what I didn't want to do.

I figured I'd try something else. I love coffee, so I started working as a barista. From there, I took on managing the coffee shop's social media and developed other skills I never thought I had.

I was also very lucky to learn social media as a skill at a time when it had just started growing. After that, I bounced around to work at shops that were mostly customer-based jobs with products that I liked. After being a barista, I worked at the plant store. I loved learning about plants and how to take care of them.

From there, I ended up in a hospitality group focused on food because I loved one of their restaurants. When I used to go, I became friends with the manager. It evolved into a role where I assisted them with social media, and then I handled brand marketing for that group.

Overall, I focused on doing jobs that combined my passions for coffee, plants, and food. The hospitality group job allowed me to wear many hats, including social media management, PR, and hosting soft openings. This job helped me realize I wanted to do events.

I feel I'm very lucky, and I don't want to jinx it. Knocks on the table. Honestly, I wasn't actively looking for any of these jobs. I always wanted to give myself a break. For example, after the coffee job, I would be walking around Williamsburg. I stumbled upon a plant store that I loved, and when I saw they were hiring, I casually dropped off my résumé. For the social media job at the hospitality group, I wasn't actively looking, but I said, "Why not?" when I was asked, since I knew how to run social media anyways. My experience evolved from there.

I've always admired your tenacity, your eagerness to enjoy life, and your willingness to learn, which has led you to form genuine connections with people. At a recent workshop that you hosted with Haco in Williamsburg, you shared with me that you met the owner because you used to walk by her shop during your breaks working at the plant store. This is another beautiful example of how your long-term connections sparked from being yourself!

To me, it also seems like you're a big people person, especially as you seek to build community. Could you share more about the ways you find to connect with other people? So when you say I'm a people person, I'm actually not. It's weird because I want to be alone most of the time. It's a funny joke with all the hospitality group friends, where we hate people! Laughing Well, we don't actually hate people, but sometimes there are just people who are tricky to deal with. No matter how solo you are, at some point, we need work and humans.

Does making connections with people matter to you, or does it just happen to you along the way? I can never work a job that I don't like. It doesn't matter how much money I earn; I would die. I think I would actually die, which is why I've ended up in jobs I genuinely enjoy. If it's something that I absolutely have no interest in, every day would be a drag. I would have absolutely no motivation—like I can't do it. Sometimes, I admire people who can actually shut that part of their brain off and go and do it. I think it's amazing, but personally, I cannot do it because, for so long, I've been free to do whatever I want and have been so lucky to be able to.

Even at my current job, of course, there are a lot of ups and downs, but in general, it's still something I very much enjoy doing. I appreciate the balance between working on production and logistics, and on event days, I also get to connect with people. I feel a lot of satisfaction when my production and logistics plans work. That, and everyone is happy, having a good time, and understands the message of the event.

Were there any career moments, projects, or experiences that you've had that really resonated with you? Perhaps something that made you feel like you had a great time and that this is the right path for you? Yes, I curated an event called "Hungry" with the hospitality group. The hospitality group itself was most focused on opening restaurants, so there was always a focus on food. The event combined food, art, and performing arts.

The idea originated from my boss, whom I really liked working with. Back when he opened his first restaurant, he noticed he had a lot of international student customers. He aimed to create an opportunity to give back to the community by providing a platform for these international students to showcase their art. To apply for a visa, international students needed to have had their art featured in an exhibition, but realistically, many of these student artists without money would face challenges doing so. We wanted to make this easier.

As a food hospitality group, we also wanted to include a food portion. In my mind, chefs are also artists, so they can curate and create food. This would also be a platform for chefs to think outside the box. We asked chefs to present their signature dishes interestingly. For example, one of the restaurants was Take 31. We created a wooden box made of plywood with holes to hold paper cones, displaying the fried chicken, which was their signature dish. We gave them a "canvas" to think outside the box that wasn't just about working in the kitchen and their usual service.

Since we weren't a gallery or in the art world, we accepted artists of various standards and levels. Again, our goal was to provide a platform for people to showcase their art and encourage them to continue creating while connecting with a live audience. You can talk about the food and your artwork. It's hard to find a platform on your own outside of your friends.

I'm very proud of that project, which took place in Chelsea with over 300+ people for an all-day event. I'm very thankful for that boss because it's all trust. I didn't apply for an "event coordinator role" because I was focused on social media. But he asked, and I said, "Sounds great." This connects back to your desire to make art accessible. In this case, you provided a platform for creatives who might not have been able to do so on their own. You ended up forming an environment that facilitates those connections happening more naturally.

At that event, you also drew all the structures yourself and designed every single piece of it. Your boss then helped elevate you in your career because he saw your potential and trusted that you could figure it out. I honestly thought working at the hospitality group would be my last job ever because I really aligned with the boss's vision and his ideas about where he wanted to do well. And you can definitely continue to carry on that message as you grow in your career.

Where do you see yourself headed next? What's the not "grand goal" but the overarching thing you want to do? Earn money? laughing So I know obviously money is important. I loved being a freelancer for three years. I felt like that was the freest I've ever been in my entire life as a freelancer as an adult. Even though, of course, it has its own struggles.

There were times that I was like, "I don't even know what I'm making this month." But you really grow and learn a lot in a short period. So, first, I'm very proud of myself for doing that. Second, I have met so many people who have become my close friends during this period. And I really value and treasure that.

I often self-reflect to think about what I'm doing now and what I'm trying to do next. I ask myself if what I'm doing now is still serving me. Or is it at least working toward something that I want?

For a long time, I've really wanted to own a space to create a retreat or workshops while being my own boss. I aim to combine the skills I've gained from working in coffee, ceramics, and plants. Ideally, this space is located upstate, easily accessible by train, and serves as a place for people to truly relax and think, or not think, about life at all.

I love New York City, and it's hard to leave, especially since my family is here. But I think the city can get a bit suffocating because there's always so much going on. I want to create spaces where people can really relax and not have to plan.

I want to create and host my own workshops. I want to bring together my musician and artist friends and help create organic connections. That would be my dream. If I could save enough to make this dream a reality, that would be amazing.

I can see that all your experiences, whether freelance or in-house, bridge together your genuine curiosity, love, and interests, as well as your connection to people. I can see all of these things converging into the following hypothesis: creating and curating a space for people to continue forming those organic connections. It's very exciting as your friend and supporter to see you continue on in your journey. Maybe 10 years later! Ten years isn't too bad—this dream will come true more quickly than we realize.

At the end of the day, why do all the work you do and the future you are aiming for matter to you? From personal experience and feeling, I know there are a lot of different communities going on right now, but I feel like there can be more. I don't want these types of communities to die. Technology is advancing rapidly; people are always on their phones or watching TV. There's nothing wrong with that, but we're not really connecting and socializing with people unless we're being forced into that setting.

The goal for the upstate space is to make it a reminder for people, me included, that you can come, stay a few days, and slow down. Relearn what is important to you in life. There are so many things that we cannot control in the world, so we really need to look into the little things and the people around us. Perhaps we can go for a walk by a field with the person you're closest to, but haven't talked to in a while, because you're always busy with something else. I want to create an environment that supports and encourages that re-connection.

Do you have any advice for a younger Ka Yee? "You did a good job."

I would tell myself that it's fine to be where I'm at right now, where I'm freelancing and doing these random jobs. While it can be tricky because I'm not "technically" building a career in the same industry, and to others it may seem like I'm just "hopping around." I would remind myself that I'm simply growing differently.

When I think back on how I would put myself down at certain times because I felt like I wasn't really doing anything or growing... I would tell Ka Yee, "You did a good job. Give yourself some grace. And honestly, you work hard! Things will align once the right time is here."

I can also see how genuine you've stayed to yourself and how that has driven you to where you are today. I also have a lot of power to think the way that I do because I learned a lot from my mother.

My mother is one of the most curious people I have ever met in my life. She's so active that sometimes I think she needs to calm down. I'm very happy for her because she's doing all the things she loves. When she was younger, she didn't have the chance to do the things she wanted because she was always working and making money for someone else. Money for her family, including her parents and cousins.

So she would always give me the power to say, "You can do whatever you want." She always told me that even though you studied fashion, you don't have to be in the fashion industry. Even though sometimes she questions my freelancing jobs, which is very understandable for traditional Asian parents, she also likes to encourage what I'm doing. She's also very supportive. Even though she might not completely understand what I'm doing, she'll always say, "Do whatever you like."

That's why I always have a mindset of, "I just need to do things that I won't regret" and "I'm just going to do it."

That's awesome when parents can encourage us. That's especially hard culturally for both of us, who grew up in traditional Chinese households and are third-culture kids. There's so much that comes from our parents' generation that they grew up in and have either learned to embody or not. My mother also doesn't let tradition dictate the decisions I make. She realized a long time ago that for her and her children to have a better future, they needed to be allowed to figure things out on their own, which is quite rare. Yes, I'm super grateful as well.

Share a list of three things you'd like to recommend. You decide the topic.

These are habits that are great to have.

1. Wake up slightly earlier than your work time. Just try it once, and if it works for you, it works. If it doesn't, it's okay. When you wake up, don’t look at your phone. Get up, go make a coffee, a matcha, or a good breakfast. Give yourself time to rest your mind and then roll into your day.

2. Play with your closet. Dressing up is fun, and now that I'm an adult with money to buy stuff, I have more freedom to try new things and have fun. Little things really add to your life. Since I work in coordination and production, I always try to dress as comfortably as possible, which can lead to wearing sweats or starting to look a little sloppy. It didn't make me feel good, so I started looking into my clothes and playing with the pieces that I had. It really adds to your life to be excited.

3. Take a walk. Take a walk between your days. A walk is so important. Try to take a walk while you're on a call.

Everyone is different, but these are things I'm trying, and they have been helping me build healthier habits, and I love it. This is advice I take for myself.

What song do you currently have on repeat?

TOO BAD by G Dragon ft. Anderson Paak

Back in high school, I was obsessed with Big Bang. I've recently been looping G Dragon, specifically the song he made with Anderson Paak. I really like G Dragon as an artist—and he truly is an artist through and through.

With the recent comeback album he launched, he also created a show called "Good Day" that he works on and, in some ways, has inspired me. He brings old friends and invites new friends into the community—some are chefs, some are in the acting world, and some are painters. And it's cool because they come together to make a song, and he doesn't have to do something like that. But because he has the money and power to do it, he can, and this is what he wants.

Enjoyed the Conversation with Ka Yee Chan? You can find her on Instagram @kaayeecc.

Ka Yee is also passionate about giving back to Heart of Dinner.

Heart of Dinner’s mission works to directly address food insecurity and isolation experienced by Asian American seniors in New York City. As part of this Conversation, a donation was made to Heart of Dinner.

You can support Heart of Dinner by donating directly.

west & ease is part of & luo studio, where I do fractional design consulting, design coaching, and host creative community events. If you’re a brand, team, or creative partner interested in collaborating, I’d love to connect. You can learn more and reach out at andluo.studio.

Meet Laura Sandoval, a Chilean and Peruvian designer and creative based in Brooklyn, NY. Laura moves through life with a deep curiosity—grounded in culture, community, and a constant openness to possibility. She reflects on growing up in the Chilean countryside, adapting to city life in Santiago, and how YouTube and filmmaking first sparked her creative drive. A short stint at film school in Peru eventually led her back to Santiago to pursue design, where she learned from niche-obsessed mentors and balanced her studies with professional work—often out of financial necessity. By graduation, Laura had already launched apps, joined startups, and found herself at Cornershop, a leading grocery delivery service, just weeks before its acquisition by Uber. That moment kicked off a whirlwind: leading design, scaling a team, integrating two companies, and ultimately relocating to New York—always following what felt possible.

Interviewed in April 2025 | This conversation has been edited for clarity and brevity.

Please introduce yourself. I'm Laura. Everyone calls me "Lau," which is short for Laura. I'm a product designer and human being. I just moved to Brooklyn from Santiago, Chile, which I'm so excited about. I would describe myself as curiosity-driven because that's what ultimately drives me.

Let's go back in time—perhaps your childhood in the countryside. Was there anything you'd like to share that stuck out to you? I really remember growing up in the countryside as a "free era." We used to live with my parents on this giant piece of land, we weren’t farmers but we did have chickens, dogs, and cats. I remember everything feeling…possible. I’d go out in the morning, explore through the fruit trees, play with rocks and sand… I remember exploring the hills around the area and having this vivid sense of freedom, which was very inspiring.

Did you grow up with many siblings or just your parents? It was mostly me and my mom. I was born in Peru—my dad is Peruvian, and my mom is Chilean. They divorced when I was around one year old, then my mom and I moved to Chile, and she married another man while my dad was still in Peru. Somewhere along the way one of my brothers, Andrés, moved with us from Peru for college.

My step dad and brother, who we lived with in the countryside, were always in Santiago —the capital city— for work and college, so it was mostly my mom and me in the countryside during the day, and they’d return at night. I did have a lot of friends from school, but because we were in a remote area, it was hard to meet people sometimes, or it'd have to be in a very arranged setting. So I spent a lot of time by myself.

What did you gravitate towards doing when you had so much alone time? I had a lot of imaginary friends, though I don't remember any of them, but my mom always reminds me. I would always be out and around exploring and "inventing" new things. Anytime I had a crazy idea, I would ask my mom, "Do you think this is possible?" and she'd say, "Yes!"

We moved to Santiago from the countryside when I was nine. My grandparents and extended family were also in Santiago, so it made sense for us to move. Moving was a big cultural shock. Moving from an environment where it was just us and nature to this huge city with a subway system and all these people and the roughness of the day-to-day, whereas the countryside was a bit more free flow and peaceful.

What was that transition from a smaller community to being immersed in the city as a nine-year-old like? What was your first impression? It was both exciting and frightening at the same time. I really struggled to fit in at the beginning, and there was a lot of bullying as well. Me being “the weird kid from the countryside” was a thing I remember. But at the same time, there were so many possibilities waiting to be explored within the city that it was also very exciting.

How did you begin to tap into those possibilities? This era was marked by the start of having internet access. At age 10, we started having internet access at home. It wasn't the internet we have today, where it's easily accessible at any given time. Wait, was it like where you'd get a CD in the mail and you put it into your big ol' computer? It was the kind of internet where you had to choose between the internet or using the phone where if you picked up the phone while someone was using it, you got the "eeeerrreeeeezzzzz" sound! Yes!!! Laughing

Since I was struggling to make friends in school, I ended up trying to find a place on the internet where I started to make a bunch of online friends—which, in hindsight, feels dangerous but turned out fine. I also leveraged a lot of the "freedom" I had when my mom would let me go, for instance, to the park by the corner near the house, but in reality I’d be taking the subway. I was a very irresponsible child, going to meet up with my online friends across the city. More than a decade later, I still keep in touch with these friends.

At the same time, I was also finding my place on the internet. I’m going to age myself here, but I loved the show iCarly. I loved the idea of having a web show, so when I discovered YouTube, I went crazy. My first neighbor in Santiago showed me that anyone could upload anything to YouTube—at first I thought only an agency could do it. It's like the one episode in The Office where Michael Scott says, "I've got to make sure that Youtube comes down to tape this."

I started uploading videos to YouTube, like stop-motion Legos and me talking to the camera. I was also trying to find a community on the internet. Were you learning how to do this on your own through the internet? Yes, and googling a lot. A lot of folks had similar experiences when the internet was coming up, and we were all really young trying to figure out things online if we didn’t know how to do something.

Did you notice if there was something you were learning that you also really enjoyed doing? The stop-motion stuff was really fun, especially spending two or three hours doing it and then seeing the final results. Not only it brought my toys to life, it also taught me how to adapt things like timing or how drastic to make the moves for it to look good. Having that quick iteration cycle going was really fun.

I was also playing with Microsoft Paint and trying to learn how to do frame-by-frame animation, which was a bit slower compared to recording with an actual camcorder but also really fun.

Wow—this reminds me of the video you created and shared about the Chilean money system. From how you confidently spoke to the camera to the editing and script, you were spot on. It came from your experience doing YouTube! A hundred percent. It was so fun for me to make because it was like a reunion for that side of my life. Like a good excuse to go into Final Cut Pro, color grade, and even experimenting with new filming techniques. I always love it when I get to overlap all the different past versions of myself.

During this time in your life, as you were transitioning into city life in Santiago and making friends online and offline, what and how did your friendships evolve? During this YouTube era, I started forming all kinds of friendships. Most of these friends were a lot older than me. I was 12, while many of them were 17 or 18, some already in college. Looking back, I have no idea why they hung out with me, but I love them and I love that they did. Back then, we’d smoke cigarettes together and go on trips for meetups with local YouTubers, trying to build community. I tried to attend every meetup, which started in local parks where I’d go by myself, but once I started having a more established group of friends, we'd travel around Chile to go to larger meetups together. Those were my first times traveling without my parents, which was scary but also exciting.

I remember going to Concepción —a city in southern Chile— a lot. I still have many friends there, and now that I’ve moved to New York, one of my besties—from Concepción—came up to help me with the move. I keep going back to this city and have such an emotional connection with it.

Concepción was also the first city I traveled to on my own. My friends and I eventually started making more friends over there and I even started dating someone, so I was always visiting. It was so much fun. With this more established group of YouTube friends, we launched our own projects, including a parody account of one of the biggest Chilean YouTube channels at the time, based in Concepción. You're just drawn to this city over and over again!

I was only 14 when we posted a parody of one of the biggest Chilean films at the time, and the film director actually reached out. All of a sudden, TV producers were asking if we wanted to work for them, and all these doors swung open toward a possible media career—it was incredibly exciting.

Were you seriously considering this career path in film? What was it like hearing about this at such a young age? It was weird, to be honest. We weren't expecting it. I was just having fun with my friends, but seeing that we could put something out there and people would find value in it, whether intended or not, was eye-opening. We’d even get stopped on the streets sometimes, especially when we went to Concepción. It was quite a niche experience.

I continued to be an independent Youtuber into my adulthood. Somewhere along the way, my friends and I ended our side project, but we continued being friends, collaborating, and traveling together.

But then, I decided to move to Peru and somewhat doubled down on YouTube. In Peru, I had a very similar experience—growing my channel independently, producing more and better quality content and seeing more people find value in it in return. It again got the point of some people recognizing me in certain places, but thankfully it always remained niché as well. It did scale to a point where it started being a bit uncomfortable for me, though. Well, yes, you're a normal human being. Exactly.

I remember this one time when I was 17 in Peru. I was unhappy with a few things in my life and thinking about moving back to Chile. I was walking down the streets of Lima, about to cry, when a girl recognized me from the internet and asked if we could take a picture. Oh no!

I did also receive so much love, which was really special. People would sometimes offer to buy me coffee or dinner if they saw me out and about by myself, and I got so many letters from younger kids in my high school who watched my videos when I graduated. I still keep and cherish all of them, and brought them with me to New York.

I moved from Chile to Peru in 2014 because I wasn't very happy there. I really liked Santiago, but I didn't like my high school. I felt it was very uninspiring. Any time you tried to do anything outside the books, the entire school vibe was to repress it in some way.

I also just hated school. I always did terribly in Santiago. In Chile, high school lasts four years, but in Peru it lasts three, so I thought it was perfect. That meant I could move and, as a bonus, do one less school year, so I left for Peru and moved in with my dad.

Moving to Peru really helped me explore my creativity more. In Chile, the school was more about getting your academics done and maybe some traditional extracurriculars like sports, whereas in Peru it was more freeform. For instance, I had some very basic knowledge on how to make and publish websites (using Apple’s old iWeb app and some YouTube tutorials), and while in Chile that was considered a distraction, or even something to make fun of, my Peruvian high school was really great at celebrating those qualities, and creating the space for students to explore them. Is this a cultural thing? I think Chile has a very strong culture of preserving the status quo. Change can be very challenging and everyone is sort of expected to do similar things, I feel like. Another example is that being a YouTuber or having side projects was very encouraged in Peru but a reason for laughter in Chile, so it was a refreshing change.

So, as you double down on being a YouTuber in Peru, what happens in this era that makes you consider moving back to Chile? It's all connected to filmmaking and design, actually.

Of course, I had an amazing time in Peru and made many good friends with whom I still keep in touch. I also made some really special connections with my teachers, who became mentors, which is very nice since I didn't really have the chance to find them in Chile.

Also, because I had these very chaotic preteen years of smoking, partying, and being out and about, I was no longer as interested in that side of things in Peru, so I really got the chance to become more professional with my side gigs. I became better at coding websites or making YouTube videos, and I started to think of those things as a potential career, especially as I was approaching adulthood at that time.

After high school, I had a booming YouTube channel at its prime. I also started working as a freelance photographer and videographer when I was 17, through a made-up “studio” I created. I coded a website for it and built a portfolio with some of my work, and called it a studio so it’d look more professional, but it was actually a one-woman operation. My older brother, who always had a business mind, really saw the value in what I was doing, so he helped me a lot.

My brother Andrés shaped a lot of who I am today. He gave me endless frameworks to think through life’s challenges, took me to New York for the first time, and back in Lima he helped me connect to people interested in my work, as well as how to charge for it. I always wanted to do everything for free because I didn't know what value I could add, but he kept me grounded and even helped me invoice when dealing with larger clients. It's great that you had someone look out for you and teach you to charge for your work at a young age. Totally, and his guidance continues to be useful today, many many years later. I’m extremely grateful to have him in my life.

So, after high school, I decided to study filmmaking in Peru. My plan when moving to Peru was always to return to Chile, but I had made such special connections there that part of me wanted to stay, so I decided to give it a shot but then quickly realized that while intentions were good and people were eager to set you up for success, the infrastructure just wasn't there yet. Film school was very cool but also very limiting. The school had only been around for like 2 years, and the Peruvian filmmaking industry wasn't as big or disruptive, so it started feeling a bit uninspiring.

When did you start to notice this? About two months into film school, I remember having too much free time and generally feeling like I wasn’t being intellectually challenged. They would teach us how to use basic software and make us do written exams on how to use stuff like Adobe Premiere—I kept thinking, why can't we figure this out on our own? It felt like we were investing a lot of time, energy and resources to learn how to use a hammer instead of how to build a house.

I also realized that, even though I loved filmmaking, I was a terrible cinephile. I haven't watched many classic movies, to be honest, and I’m not as drawn to them as I feel like I was expected to be. That's how I feel about design sometimes.

What happens next after you realize that filmmaking and film school in Peru weren't the path to go down? I got into a fussy moment career-wise. Filmmaking had been such a core part of my life at that point that without it I wasn't really sure what I wanted to do next. And so, my brother, once again saving the day, said “let's think about where you’d want to go, and then we can reverse engineer which career path could take you there.” Jamming with him about this made me realize I ultimately love creating, and putting things out there into the world that hopefully add value to people’s lives—filmmaking was one of them, but it wasn’t the only one. We arrived at design cause it felt like the most flexible path forward. I could still design a film or a media piece, but I wouldn’t be limited to one format. I started looking into design options in Peru, but they were basically non-existent, so I ended up going back to Chile, which has one of the best design schools in LatAm.

I didn't really learn about design until I got to college. I wasn't exposed to the career nor knew it was a viable option until maybe then. When did you know doing design was a career? I was always very interested in technology growing up. In parallel to this YouTube era, I’d always be mocking up graphics, websites, and eventually even basic apps on software like Keynote or iWeb. It proved really useful to support the sidelines of my YouTube channel, too. On top of this, my brother would always talk to me about new trends going on at the time, like “design thinking,” so by the time I joined college I guess it wasn’t completely foreign to me, but it was definitely recent knowledge as well.

So, how did the move back to Chile happen? Similarly to how I moved to Peru, I asked my mom if she would receive me back, and she generously said yes. So I quit film school and spent a few months doing nothing but my YouTube channel, while waiting for the second admissions window to open. At this time, I also began to have a slight obsession with transit.

Slight derail —pun intended— but navigating Lima as an adult feels very different from navigating Lima as a teenager. Lima is a very large and chaotic city, so moving around is tough. Lima’s first Metro line opened in 2014, almost 30 years after construction began, which is insane. People mostly move around through shadow buses called “combis”, which are insanely cheap but have a lot of unwritten rules around them and aren’t the most reliable. This lack of infrastructure made me realize and appreciate how lucky I was in Santiago to have things like predictable routes, a stable and growing subway system. In contrast to Lima, Santiago opened its first Metro line in the 70’s, and is on track to open its 9th line by 2030. Thinking back to my 10 or 12-year-old self, navigating the subway and being able to move safely around the city was really special in hindsight.

I began obsessing about transit as a service and how different cities approach it, optimize it, and ultimately design it. I asked myself, if Santiago was to design a graphic identity for its transit system, how would I approach it? What do other cities take into account for theirs? I read about Transport for London, the MTA, the beautifully designed Moscow Metro Map, and ultimately allowed myself to wonder and explore these questions through design, always sharing my thoughts and explorations on the internet.

This created a great vicious cycle for me cause it ultimately allowed me to jumpstart my design career through something I was personally passionate about, and by the time I started design school, I already had a small design portfolio and had met with all these people in the industry who were somehow interested in what I had to say, from academics to Chile’s own Vice Minister of Transport, who eventually became a Twitter mutual.

That's awesome. When I speak with early career designers, many are conflicted about showing "real projects" on their portfolios. What you had was a real project—you conceptualized something, shared how you made it real, and had conversations that grew from it.

Totally. The main difference between a real and conceptual project is usually that one was "requested" versus the other wasn't, but that doesn't really matter at the end of the day. Design can be a really powerful tool to express a point of view, and to visualize how we envision reality to be. Whenever I talk with early career designers, I try to emphasize that we don’t need anyone’s permission to do that.

How and when did design school come in? Taking a step back, so in Chile you need to take some standardized tests to get into college, but because I finished high school in Peru, I had a slightly different process. I didn't realize it then, but applying to design school through this special process was a very competitive and risky move, cause there are only five slots per admission cycle, and you’re competing against up to 60 other folks looking to get in through one of them, including Chileans who studied abroad, people with special needs, distinguished sport alumni, etc.

The most crucial part of the process was an interview with the curriculum director and a panel of teachers who evaluated each candidate at the end. It was sort of like a job interview—they asked questions about design, how I’d approach different problem spaces, and most importantly, what would I do if I don’t get in. The fact that I had all this work prior to the interview—the photography & filmmaking studio, the transit design projects, etc—made a world of difference, because I was able to let my work speak for myself.

Everything was publicly accessible through my websites, so they were able to see it during the interview and ask questions about it. I told them if I didn’t get in, I’d double-down on these projects and reapply on the next admissions cycle, but luckily that wasn’t necessary. Wow, and the question "What would you do if you didn't get this opportunity?" is such a good one because it can be tough to answer. Totally. It caught me off guard at the moment, but I’m happy I could leverage it to showcase my work. The school’s academic coordinator later told my mom and I as I was enrolling in school, that the panel had been “blown away” by it and were honored to have me. It was truly special.

What was your design school experience like? My design school was an aggregator of very talented folks, each with their own niché interests. My curriculum director, who later became a dear colleague and mentor, was also obsessed with transit and had his own wayfinding design studio on the side. We’d talk for hours about maps, mobility, graphic design, typography. I had teachers obsessed with color, science and history. I had teachers who had dedicated their careers to lighting design, and some who obsessed about fashion or the political implications of what we were putting into the world. Everyone had their own interests and unique path to design, and the combination was truly greater than the sum of its parts.

We all started on the same curriculum, where we studied the history and foundations of industrial and graphic design. It was the opposite of my experience at Peruvian film school in that the emphasis was always on teaching us how to think and quickly exposing us to trial-and-error cycles, rather than leading with specific tools. We almost didn’t touch a computer for the first few years. We’d do lots of sketching, paper-cutting, and research, and present weekly progress on our assignments through posters or decks we also had to design. We’d spend days at the workshop working with wood and take turns sleeping on-campus while working with fiberglass throughout the night. I learned very quickly that I was terrible at industrial design.

I guess my journey—I don't want to say it got interrupted—but my first year was marked by my parents not being able to afford design school anymore. My student loan didn’t cover the entirety of the cost either, so it was either quitting design school or figuring out a way to pay for it by myself, which is what I ultimately did.

I began socializing that I was open to work and, thankfully, managed to get the ball rolling quickly. I got poached by a local graphic designer—who was familiar with my work through Twitter— to work as his assistant for a few months. My curriculum director, who had always said he’d love to work with me at some point, then offered me an assistant role on a last-minute project to redesign Santiago’s transit graphic identity. Eventually, I landed at a local cycling-tracker app start-up as a Design Engineer, thanks to the founder also knowing my work through social media.

As I navigated the professional world and learned from all of these designers who were far ahead in their careers, college started to become a background activity. I had very little free time, juggling both work and college, so I began optimizing my college involvement to prioritize the two or three classes I felt most beneficial for my professional growth, and did just enough for all the rest.

Did you finish college? I did. Chile has an extra year compared to the United States, so we have a five-year program. I finished at the four-year mark, the bare minimum for the US and the rest of the world. Some industries in Chile, like the public sector, would limit my seniority for not having that fifth year, but it’s not really the case elsewhere and even internally it can be replaced by a masters degree if I wanted to.

I ask about finishing school because not everyone does. Yet, finishing school doesn't equate to success. It's more about personal decisions and timing to get you where you want to go versus checking every box. In this case, since you were already working, you decided not to check the fifth-year box. Absolutely. Some of the best designers and product thinkers I’ve worked with didn’t have a college degree, including my old company’s Head of Design and Founder/Head of Product. It’s a really personal choice. I did want to quit at many different times, but was encouraged by many mentors —including my brother Andrés— not to, since having a professional degree would be really helpful if I ever wanted to expand outside of Chile. Once again, he was right!

How did you go from finishing your degree to becoming the Head of Consumer Design at Cornershop? I started leading Product Design for Consumer apps at Cornershop —the largest grocery delivery app in LatAm— in 2020, but 2019 was the year that glued all the pieces together for me, and really solidified the foundations for everything that came after.

While I was working as a Design Engineer at Kappo, the cycling-tracker app, I was lucky enough to pick-up a few high-paying freelance jobs. My curriculum director and I had become close working buddies at this point, so he’d always call me to collaborate on new gigs. I was able to pay off the remaining year of my college tuition in advance and shifted gears to my next personal goal—moving into my own place and becoming financially independent.

At this point, I had also launched a few independent transit apps, like a Facebook Messenger chatbot for Santiago’s transit system, which the Ministry of Transport tried to acquire the year prior, and an iOS app for checking your transit card balances, which I still maintain to this day.

Since I no longer had to earn a steady monthly income to cover my college tuition, at least until the next year, I quit my job at the cycling-tracker app and started thinking about my next chapter.

One random night, I stumbled upon a tweet from Cornershop’s Creative Director, Daniel López Rivas, who was both a Twitter mutual and the owner of one of my favorite coffee shops in Santiago, saying Cornershop was hiring across most of its departments. We were both familiar with each other’s work, so we got to talking and he introduced me to Matías Martínez, the company’s founding designer and Head of Design. He was also familiar with my work.

As a side note, it had always been my dream to work at Cornershop. I had been a loyal user since I moved back to Chile in 2016 and always admired their craft and commitment to quality. They were truly unmatched. I actually applied to work there as a customer service agent back in 2016, before starting college, but was rejected. Well, thank goodness, because it led you here!

Exactly!

So I started chatting with Matías on a Tuesday, right after talking to Daniel. We met for coffee on Thursday —at Daniel’s coffee shop— with Matías and Osvaldo Mena, Cornershop’s Head of Engineering at the time. They both had my apps installed on their phones. We talked for a few hours, discussed my salary via Twitter DMs the night after, and I joined Cornershop the following Monday as a Design Engineer. It’s the fastest I’ve ever been hired, I think.

Incredible. Around 2021, I recall Uber acquiring Cornershop, which led to us eventually meeting in 2022 and working together. Could you share your experience leading up to the present day, especially from being part of a team going through an acquisition? Joining Cornershop was a pivotal moment in my career. I remember going into the office before and after classes feeling a strong sense of “wow, what the hell am I doing here?” We were around 300 people, maybe six on the design team, and everyone was so talented that I felt like I was learning more each time I went into work than I’d learn in a month of design school. It was truly inspiring.

And to make things even more exciting, right after I joined, news broke that Uber was acquiring a majority stake in Cornershop. I remember my brother texting me that day: “Did you just accidentally land a job at UBER?” I couldn’t believe it.

A big part of why Cornershop hired me in 2019 was my independent apps—I wanted them to feel smooth, snappy, native to mobile phones, but I only really knew how to code for the web, so they were actually coded like a website, but packaged like an app. I spent hours obsessing over the details, and would always be studying ways to make them feel snappier or to make interactions smoother. I remember Matías —who’s also the best iOS engineer I know— telling me he thought my apps were native felt like my biggest achievement.

Coincidentally, Uber wanted to leverage Cornershop’s tech stack and expertise to tap into the grocery delivery market, and Cornershop wanted to leverage Uber’s scale across Rides and Eats to reach new customers, but delivering groceries is a whole different game than delivering on-demand meals, so we couldn’t “just add grocery stores” to Uber Eats at the time. Building support natively would’ve been a gigantic undertaking, especially pre-pandemic where demand didn’t quite justify it yet. So both companies decided the first step towards integrating would be to somehow integrate Cornershop’s website on both Rides and Eats. The big issue was… it felt too much like a website. It didn’t even work on mobile.

Matías and Osvaldo quickly tapped me for the challenge, and I was asked to make Cornershop’s website “responsive”, which would eventually allow us to theme it as an Uber product and plug it into Uber’s ecosystem. I guess I had the right obsession at the right time!

Taking on this challenge was no easy task though. It was my first time working on such a large codebase, so I leaned heavily on more senior engineers to navigate it. We ended up rewriting almost 20 thousand lines of code—at a time where “vibe coding” and generative AI weren’t a thing. Again, I obsessed over the details to keep the illusion of a native product. I wanted Uber Grocery to feel like a first-class citizen in Uber’s ecosystem.

All of a sudden, I found myself invited to all these sessions and dinners with the Cornershop founders, including the CEO, and Uber executives flying to Chile to check-in on what I was working on. The first time I gave a demo to the team, I remember everyone going: “Are you sure you’re on the website and not the app?”

We launched Uber Grocery only 5 months after, and added more than four billion dollars in annual recurring revenue through it in the following 3 years, before sunsetting the website.

As we scaled Cornershop towards the end of 2020, we decided to split our Product Design team into verticals. Our once-300-person startup was now on track to hire its 1,000th employee, and the timing felt right to scale our design operation into more focused pods. As soon as I graduated college, Matías asked me to lead Consumer Product Design. By that point, I had a proven track-record of shipping high-complexity projects, had worked with both Uber and Cornershop leadership, and, in the words of Matías, “couldn’t be fooled by less-committed engineers.” thanks to my early exposure to all sides of the business. He said he “couldn’t picture anyone else taking the role,” which was truly special—for me, it was a testament to all the previous pieces of my career coming together for the first time.

I was tasked with hiring our Consumer Product Design team, and leading the way for our iOS, Android, Web, and now Uber apps. It was one of the most challenging but fulfilling periods of my career.

And once again, you were open to the possibility. True! Thus, you were able to embrace the experience more. Your natural disposition seems to be to embrace what's possible, which is awesome!

Shutting down Cornershop and transitioning the team into Uber was a similar story. Uber had acquired the rest of Cornershop in 2021—making it the first Chilean unicorn and the largest acquisition of a Chilean company to date, and leadership decided we’d integrate everything natively the year after.

As a few folks prepared to leave, including our Head of Design, I randomly got a meeting invite on my calendar from Uber’s LatAm Grocery Director, who was acting as Cornershop’s interim “CEO.” The meeting was just him, me, and my HR rep. Honestly, at first I thought I was going to get fired. I had never spoken with him before, but he knew exactly who I was and wanted me to integrate Cornershop’s Product Design team—which had grown to 37 Product Designers and Design Managers across five verticals at that point— into the Uber org. He thought we’d only be able to migrate six or seven designers, so his ask was that I figure out the best way to navigate this and migrate as many people as I could. Woah! I had no clue that happened.

I had no instruction manual, but nor did I have one for anything that came before! So I just said “sure, whatever, we'll figure it out.”

Cornershop was pretty much still an independent company at this point, so I started by building as many bridges as I could. I set up a recurring meeting with Uber’s Delivery Design Director, met with Uber’s Delivery Design Program Manager to get a better sense of how things worked and how my team could better support the company’s design needs, and started poking around to meet with as many Product Managers and Designers as I could, to get insights, gain momentum and hopefully accelerate collaboration. My time with design leadership was limited, so I felt like the most efficient way to approach it was to gain as much context as I could myself instead of waiting for those times to get it. That way, when the time came to discuss logistics, I’d already be familiar with what was going on, and could identify collaboration opportunities independently.

On the other hand, at Cornershop, we didn’t really have much documentation or formal processes for a lot of stuff, so I worked with our own Design Leadership to proactively set up documents and Google Sheets for anything we anticipated could be useful during this time, like performance reviews, featured projects per designer, strengths, career paths, etc. It was, again, all about optimizing for efficiency and making sure we had everything we needed during those small decision making times with Uber’s Design leadership. I also started sending weekly updates to our broader design team —who had been navigating uncertainty for a while— to give a sense of momentum and continuity.

In the end, we managed to migrate at least 13 designers —more than twice than we’d initially estimated— to full time roles at Uber. It was bittersweet in that I had to let go most of my team, but this was also the first time in history a Chilean start-up integrated into an American company like Uber, so I’m extremely proud of the work we did.

Your role has shifted since joining Uber—what was that transition like for you?

Uber’s leveling process for Cornershop was a bit strange in that seniority levels were assigned by salary instead of role, capping the levels at “Senior” —typically reserved for department heads—and prorating by salary bands below. In my case, because I reported to our Head of Design, I was leveled one level below senior, and had to switch back to being an individual contributor to continue at the org.

We all got our levels as I was leading the migration, so this obviously blew up internally and suddenly I had to be the face of bad news. My main focus was on getting as many people as possible a role, and making sure all voices on the team were heard, so I remember spending many late nights on Slack DMs or impromptu Zoom chats with HR or the founders, who at this point didn’t have that much power themselves. I wasn’t paying much attention to my level in particular, and instead decided to trust that things would naturally find their place in the long run, and I’d find my place to add value again. Obviously, you've been able to do that to become a crucial member of the team.

Since joining, you've recently moved from Santiago to New York! What spurred the international move? I always dreamed about moving to New York, but never thought it’d be possible in my lifetime. I dreamt about it as a child and fantasized about living here when I visited for the first time in 2015, but could not see a path where that would happen unless maybe I studied for a Master's Degree or something like that. Uber has really changed possibilities for me in the last few years.

In 2023, I got to attend the Grace Hopper Conference, one of the largest conferences for women and non-binary people in tech, held in Orlando, Florida. I remember coming back to Santiago afterwards feeling not only inspired. But also like, regardless of my employer, I wanted to be where the action was.

At the same time, I had just bought and remodeled my own place in Santiago a few months prior and all the incentives keeping me at Uber—inherited from my previous role at Cornershop— were approaching their expiration date, so I found myself in between crossroads. Looking ahead 1 or 2 years into my career, for me it was either leaving Uber to start my own thing, or doubling down and pursuing an international move. It seemed personal and professional became intertwined.

Now that we're in the present day and you've moved to New York, why do any of your experiences or decisions matter to you? There's something inherently fun about making things that other people use. And so, looking back from the YouTube days to designing for Uber, I feel like the underlying fun part for me is the same. Working on something that’s bigger than myself, getting to meet and collaborate with fun and talented people in the process, and people finding value in what we decide to put into the world at the end—and then doing it all over again.

What advice would you give to a younger you? I probably should've been more unhinged. laughing Wait, explain! Well, thinking back to when we launched Uber Grocery, for example, I spent my 22nd birthday on Figma and VSCode rushing to get all the details ironed out for our upcoming launch the week after. It was a Sunday, and I had both college & work the next day. Sure, we were well paid for it, but in hindsight—I probably should’ve been at the club.

I'd also tell my younger self that being confident in your work is not an inherently bad thing. I feel like I lost a lot of time dismissing my wins and jumping too quickly into the next goal, but taking things a bit slower could have been cool. I feel like all these things happened so fast. Right, and you've just arrived in New York. No, literally. Sometimes, even in Santiago, I would look around my apartment and wonder, "How could I even afford all of this? How and when did all of this happen?"

It would have been nice to allow myself to enjoy each moment a bit more. I'm trying to be more intentional about practicing that as I get older.

Could you share a list of three recommendations—you pick the topic.

I have a gazillion iPhone notes of random things I could recommend! One of my favorites is music albums. These are some my favorites lately:

1. Terrace Martin and Gallant's Sneek. From 2023 but I only discovered it recently. Love the little jazz bits and how modern it feels at the same time. Great for sketching, doing something chill, or just appreciating the view. I wish I could listen to it for the first time again.

2. 47 EP by Chezile. I stumbled upon a song from this album on an IG post and immediately went looking for more—and thank god there was! Loving Chezile’s work so far and can’t wait to see what he does next.

3. Feel feelings by Soko. Another one I wish I could experience for the first time again. I had “Replaceable Heads” on repeat for most of last winter. 20 out of 10.

What song do you currently have on repeat in the same music theme?

La trama y el desenlace by Jorge Drexier

This is one of my favorite songs of all time, by one of my favorite artists of all time. Jorge Drexler originally studied medicine but later pivoted to his actual calling in life and became a musician in his early thirties. Since then, he’s earned 15 Latin Grammys and was the first Uruguayan to win an Oscar for one of his songs. “La Trama y el Desenlace” (“The Plot and the Unraveling”) talks about how sometimes beauty lies not in grand finales, but in the unraveling of the everyday plot.

Enjoyed the Conversation with Laura Sandoval? You can find her at

https://lausandoval.com and @laurasideral on Instagram, X, and LinkedIn.

Laura is also passionate about giving back to the New York City Dyke March.

The New York City Dyke March is a protest march where thousands of Dykes take the streets each year in celebration of beautiful and diverse Dyke lives, to highlight the presence of Dykes within our community, and in protest of the discrimination, harassment, and violence we face in schools, on the job, and in our communities. A donation was made (by west & ease and matched by Laura!) to the New York City Dyke March as part of this Conversation.

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west & ease is part of & luo studio, where I do fractional design consulting, design coaching, and host creative community events. If you’re a brand, team, or creative partner interested in collaborating, I’d love to connect. You can learn more and reach out at andluo.studio.

Meet Hope Idaewor: a Nigerian-born, Atlanta-raised design researcher, educator, and mentor based in Seattle, Washington. In this conversation, Hope opens up about her experience growing up in a Nigerian-American household, and how her father played a pivotal role in shaping her self-confidence and pursuit of excellence. She reflects on the formative moments that introduced her to the world of computer science and UX research—some inspiring, others challenging—and how building confidence helped her push through the discouraging parts. We dive into her focused work ethic, her determination to break into the tech industry, and how that drive has carried her through roles at major companies like Microsoft, Uber, and more. Hope also shares what it means to her to give back—whether it’s mentoring others or staying grounded in family life as a mom and wife—all while continuing to grow in her career.

Interviewed in January 2025 | This conversation has been edited for clarity and brevity.

Please introduce yourself. Hello, everyone. I'm Hope Idaewor, a Senior Researcher at Microsoft. I'm currently living in Seattle with my husband and son.

I immigrated from Nigeria as a kid and grew up in Georgia. A lot of my life experiences, how I was raised, and how I navigated my life all connect back to my roots. My culture is very family-oriented, and I am the first child of five kids. It also brings in a piece of my personality—that go-getter mindset I’ve developed over time. Being the first in my family to go through college in America, I didn’t have a choice. That drive had to be there.

Pursuing a career in tech started from home. My dad is a self-made entrepreneur and IT consultant and has been in the tech industry for 20 or 30 years since being in this country, and he's done a lot of amazing stuff. It's a huge inspiration and connects to why I chose to get into Computer Science.

What do you think makes your upbringing unique and how has that shaped who you are today? I grew up in America but consider myself a Nigerian American, with my upbringing in a relatively traditional African household. My perspective now differs from when I was younger and how I saw my upbringing.

What was your perspective then versus now? I don’t think I realized how much my parents truly sacrificed until I got older. My dad started from scratch, working on his PhD in Economics in Nigeria to then come [to America] and started from blue-collar jobs, then eventually pivoting in a completely different space. He got into tech as a database administrator. He got in around the internet boom and landed a job at Oracle in the late 90s and early 2000s—when everything started. He came in at a good time and was observant enough to discover that having skills in tech was becoming increasingly important.

That's why he picked that career path. He taught himself database management, consulted for several companies in the U.S. and globally in the 2000s, then decided to help others and opened an IT training academy. He started pouring back into the diaspora, helping other immigrants and people of color up-skill themselves the same way he did.

So that was immensely inspiring, he got me my first computer when I was about 7 or 8. But there was some internal pressure I think that came with it, that I felt growing up. Having A's was expected, and I did well in elementary school. But when I got to middle and high school, I started to get into the social element, and I struggled with really stepping into myself. Where we lived in Georgia, there weren't a lot of immigrants or Africans living there at the time, so I started to feel like I needed to fit in somehow. For example, I would start unknowingly masking my accent to fit in more with the American kids (both black and white), and simplify my last name so my friends could pronounce it “better.”

I started to get more focused on fitting in, dating, than on educational excellence or joining academic clubs that would help boost my resume for college. When it came time for high school graduation and applying for colleges—I didn’t even want to go to the University of Georgia at first. It’s one of the top public schools in the state, so of course my parents were pushing for it. But back then, I just wanted to follow my friends who were all going to a different school in the state. My dad ended up forcing me to apply and accepting the invitation to attend. I was pissed.

Looking back at it now, that was the best decision he ever made for me. I met a lot of great people from all over, learned a lot, started to openly embrace my Nigerian identity for the first time, and truly grew out of the “bubble” I grew up in.

So that's an example of perspective shifting as I got older, but it also reflects the pressure of growing up in a first-generation household and as someone shaping the way for the rest of my siblings.

Were there any particular values that your father wanted to instill in you? What helped you realize his guidance helped you make the best decision for your future? He was trying to get me to always reach for the highest bar, shoot for the best, and see the best within myself.

He started from scratch and self-funded and started several businesses even after his academy. So he always instilled this value of, 'You can be excellent. You are excellent. You just have to do the work to get there, but also believe in yourself and that you can do it.'

He also ensured that I understood what it meant to think independently and be my own person rather than following others. That guidance and support, along with my own decisions, had a lasting impact. There's almost this shortsightedness that you have as a child, and your parents are there to guide you and ensure you can see beyond that.

Your dad also tried to push you to be yourself. I can see where who you are stems from that part of your upbringing, which involved having someone, in this case, your father, be confident in you to help you see the confidence in yourself.

So, what happens next as you decide to study at the University of Georgia? Were there any key moments that helped you as you entered the working world or as a young adult? Yeah, gosh, it's so hard to summarize because so many things happened in those four years!

But three things come to mind.

For context, since my dad always had computers around and got us personal computers pretty young, I always dabbled in coding. I taught myself Graphic Design, HTML and CSS in high school. Then I decided to pursue Computer Science since it felt the most relevant to my interests.

First key moment: my very first computer science class is the most memorable thing that comes to mind. My instructor was a guy who worked at Google as an intern and was also a PhD student. I remember the first day when I walked into the auditorium-style class; I was probably one of four girls, and one of two black people in the class.

We first started with a "Hello World" exercise in Java. All I remember is how technical and nerdy it was, but how genuinely happy and excited I was. It was very interesting, seeing how simple commands could make my computer do certain things. It was literally a new language, and I couldn't wait to learn more.

The way I look at our careers and the things that we do and spend 40 hours a week on, I think we need to love what we're doing and that there should be some connection that doesn't make it feel mundane and still feels integrated into our life, purpose, and all these things.

And I remember that day saying, "Oh my god, I can't wait to continue to learn software development and to be this developer and write more code." Granted, it became much more difficult after just coding "Hello world."

That moment was memorable because I remember how I felt in that class regardless of being the obvious minority in the room. I didn't really feel any “imposter syndrome.” At the moment, if anything, that was overshadowed by me just feeling like, "I can’t believe I get to actually do this every day.”

The second key moment is almost the opposite of that first memory in my first year of taking that first Computer Science class.

In senior year I had an appointment with my research advisor, the head of the Computer Science department at the time.

We were preparing for graduation and I needed four remaining Computer Science classes. I was a little behind in a few credits as I didn't take the right classes freshman year, so I needed a bit more to graduate on time.

The research advisor told me, "It's not possible for you to take these four classes and graduate in the spring. You're not going to be able to do that. He said, “my smartest students can't do that. You definitely can't do that."

Looking back at it, I actually agree that taking that many CS classes at one time was a bit of a stretch, but there was a layer of disbelief and disappointment I felt, in how he was so quick to assume I would fail before I tried. It wasn't a conversation. It was like he just made up his mind and was telling me I was out of luck.

After that meeting, I registered for the four classes that semester and passed them all. Guess who shook my hand and handed me my diploma on graduation day?

That memory stands out to me because that was a time I believed in myself even when someone told me I couldn't do something. Because back in high school, I didn't have many of these moments where I felt like I could do something on my own or even had support from someone to go against the grain.

Finally, one last moment, probably the most important, was when I went to the Grace Hopper Conference during my junior year in college in Phoenix, Arizona. I loved this conference—it was inspiring, just great. I ended up meeting a black woman who was a UX researcher. It was the first time that I met someone in the CS field who was a researcher, AND who was black.

I vividly remember her describing what she does: a UX Researcher is someone who might not be building or designing a product, but helping advocate for what's being designed and built. She also described herself as a cross-cultural researcher, someone who studies behavior in different countries and identifies cultural patterns in beliefs and values. It was like a lightbulb went off in my head. That instantly connected with me because of my own personal experiences navigating my identity as a Nigerian growing up in America. So, the idea of advocating for people of different backgrounds in how a product is designed was fascinating.

That was also the first time I heard of UX Research as a position, and this moment led me to take HCI (Human Computer Interaction) courses during my senior year of undergrad then eventually pursuing a Master's degree.

Was that the moment that helped you pivot towards a different career path, or did you feel you could keep going where you were? I don't think I decided at that moment to scrap my dreams of being a software engineer. It was more of a mental note, "Wow, [user experience research] sounds exciting—maybe more exciting than the idea of coding." I eventually want to get into UX research, and I knew my degree would still get me there because, at the end of the day, it's all under Computer Science and Computing.

The HCI courses helped me see what it meant to do research, its connection to human factors, the design process, and all of that, which was a good primer. But realistically, I had a Bachelor of Science in Computer Science. When I graduated, I had to find a job and start as a software developer because I thought, "What else am I going to do?"

So, I got a job at a consulting firm as a software developer, and I did that for two years. At the end of the two-year mark, I said, "All right, it's time for me to figure out how to get back into UX."

What was your journey like transitioning careers? What were your first steps, mishaps, or lessons learned along the way? While I hadn’t always been resourceful [thinking back to high school], eventually, I became a person who was more committed to seeing myself achieve my dreams and goals. That comes with learning how to be resourceful, learning to learn, to connect with people, to advocate for yourself, and to find champions.

I wanted to understand the UX field fully, not just the surface. I read books, I went online and completed certificates. I also reached out to as many people as I could. Many of these were people I randomly reached out to, so that meant there were a lot of rejections or people who just didn’t respond. But there was this one woman who actually took the time to speak with me, and had several mentoring calls with me. She was a designer at Publicis Sapient, a design agency. I also reached out to the woman from Google that I met a few years back.

I learned I needed a portfolio to showcase that I understood the design and research process, and that I really needed to show project and team experience. So, I immediately started working on my UX portfolio.

At the time, I was still working as a consultant. I was making weekly trips between Atlanta and Connecticut for two years, which was a bit stressful but a fun experience when you’re young. One day, during one of these trips, I met an older woman who owned a special collections library with her husband. During the conversation, I offered to run a heuristic evaluation on her website and do some light research to help her better understand the needs of her target audience. And just like that, that became the first project in my portfolio.

So, little by little, I found projects to put on my portfolio and eventually got interviews for user experience research and design. While I could get through the door for the first interviews and screening conversations, I was missing that product sense/team experience and was not getting called back. But it was good practice.

I eventually realized I would need to leave my job to fully focus on this thing. This period was around 2015 and 2016, and UX was very much an established field, about 15 or so years after being an official industry.. Yes, roles were starting to get more definitions around them. Exactly, and so there was more investment in UX at different companies with many roles open then. But it still felt like it was more of a specialized field where "you need experience to get experience." So it was very difficult for me to break into the industry, with no formal training outside of small business projects and software development experience. I probably got at least five interviews though, which was impressive to me because I didn't even have a lot—just a rough portfolio and dreams.

What stands out is that it shows you were doing the work. Some people wonder, "Why can't I get a job?" It comes down to being focused on your goals. You took a chance in the conversation with the woman on the plane and all the people you’ve reached out to, which is important.

In mentoring early-career individuals, I often find that many aren't willing to go the extra mile. Doing unconventional things, like offering free design services helped me land my first clients as well. Unfortunately, getting ahead isn't always tied to only getting paid opportunities. You have to be willing to put in the work to break into the field.

Moving forward in your career timeline, I'd love to hear how you landed your first role as a User Experience Researcher at ALU Education. Going back to the examples of shooting my shot and reaching out to as many people as possible, being laser-focused is a very good way to describe my mindset at that time. The biggest reason I could transition successfully was because of the connections I ended up making.

It was summer of 2016 and one of my friends introduced me to a PhD student studying HCI. From his perspective, he felt I really needed the academic rigor and foundation in HCI and Human factors so I began to entertain the idea of grad school and decided to apply a few months later.

I learned about the African Leadership University from a friend. It is based in Mauritius. The fellowship program aimed to create a first-in-class university and grow and retain talent on the continent. I worked there as a program advisor, where we participated in leadership courses, advising students, and shaping the university programs.

One day I raised my hand and offered to help out with UX projects. I got this wonderful job as a part-time researcher for the learning management system they use. I did some usability testing and helped them improve their implementation. It was the first time I was working with a team of other designers and researching with the team, and it was great.

What also sets you apart in your journey is that you raised your hand for something that wasn't your "assigned role" but drove you toward the direction you wanted. Personally I think it was just God aligning things and me being laser-focused and knowing what I wanted.

I was at ALU for six months. I then came back to the States, went to grad school, did some internships, and eventually got jobs at Intel and Microsoft. Everything that happened was a product of both my faith as well as showing up and doing the hard work.

Now that you've transitioned back to Microsoft, were there any moments from ALU to now that stood out to you? One of my first roles was working on a large-scale project at Microsoft. I co-led an ethnographic study on employee experiences for the first time when I was here. That was a great role, but I was still fresh in my career and struggled a bit to navigate research at that scale outside of an academic setting. What I learned later after having worked in the consumer space at Uber then returning to Microsoft over the past eight years is that research is only a portion of our jobs as researchers. You have to spend a lot of time outside the research studies learning the business and building relationships and trust across the cross-functional team.

Having a great manager and champions that support you really matter, as well as having more senior researchers you can learn from.

Definitely—it's not always about being purely a great researcher, but similar to running studies and gathering insights, it's also about understanding context and having the support scaffolding from your team, manager, and others to allow you to continue moving forward in your career is crucial.

And how do mentorship, coaching, and the UXR courses you create come into your career? I started working on hopetalks.design two years ago on and off because I realized I would hear the same questions from people time and time again, such as "How do I stand out in my career?" or "How do I get into UXR?' It's tough to answer because I don't think everyone needs to follow the same path.

But then I reflected on what I would tell my younger self as I entered the field. I channeled that and started writing and creating my own perspective of the research field. I thought deeply about characteristics and qualities that researchers should have, things that helped me, and how to build that support system.

I started by hosting free sessions, getting to know people who were early in their career and offering advice on how to decide whether a certain industry is even right for you and your goals. I wanted to show up for people in the ways I needed when I was new to the field and cold emailing others as well.

As I was doing these sessions, and navigating work, motherhood, , I had a lot of things going on in my life as well, and it started to take a toll. I needed to find balance and decided to begin charging for my time. If I was going to dedicate hours reviewing resumes, helping people tease out their core values and research strengths, I wanted to know both parties were fully committed.

So, while I still do free sessions if someone reaches out for them for some quick advice or to connect, I also offer more detailed sessions where I invest more time in co-creating career strategies with my clients and coaching them towards their next role. One message I try to convey is harnessing your superpower. What makes you unique and stand out?

Exactly—what's your differentiator? That's what really helped me. Regardless of how I got into the field, I don't think everyone will have the same career path, but the value that helped me was being laser-focused on what differentiated me, who I was, how I wanted to show up, and what unique soft and technical skills I had to offer. Balancing that kind of confidence with a desire to continue learning is powerful.

So, I share that through my platform, encourage people to harness that, and figure out what differentiates them. For example, I might meet someone who is currently working in clinical services and they are trying to come over to design and tech. I help them figure out, "What are your values? What brought you to clinical services? And why do you want to enter the design and tech field?" I get them to think deeply and reflect their values systems and connect them back to the hard and soft skills they are uniquely gifted with.

What I hear is connecting back to the roots of what you experienced in your upbringing and as you navigate your career: hearing what others might be saying but then figuring out your voice and perspective. And that's what you're doing with hopetalks.design to help people shape that personal narrative versus just telling them what to do.

Reflecting back, what advice would you give a younger version of yourself? I would tell my younger self to get out of my head, get out of silos, and connect with people early. Coming from academia where I spent 2 years going really deep on a thesis, I learned the hard way that it is important to bring people along with you.

You also need to build trust and credibility with others on your team and leaders in your organization. So, I'd tell myself to stop working in a silo so much and to “manage up” a bit more, being vulnerable where it makes sense and bringing people along as I work on a study, even if it doesn’t go well.

I'd also say lean into your voice. One thing I've learned in my career is that a lot of people don't always speak from knowledge or know what they are talking about, oftentimes the loudest in the room pushes the agenda. I wish I had leaned more into my instincts and not been afraid to ask certain questions in a meeting, not being afraid to speak my mind when it matters, and not let people discredit me or take credit for my work. I would tell my younger self to have the wisdom to know when to speak up for something I believe in or want to advocate for. That took me a while, especially in the corporate environment. And finally but most importantly document your impact and the different ways you've made an impact across various roles, that’s your brand.

Lastly, I would look at my career not as all the places I've worked with as "this is work I did at Microsoft" or "this is work I did with Intel," but as these are all skills that are still part of me. I look at my career as a whole package. I have the company I worked for and I have my brand. I'm my own person, and I have these skills that I've gained—interpersonal and technical—across several industries. That’s valuable. I also have my own perspective on the world based on my upbringing, how I view the world, and the experiences I've had, which are also valuable.

It is a good reminder because oftentimes, when we spend 40+ hours a week on something, that becomes a lot of our identity. How do you ensure you don't get absorbed into the big corporation but are still your whole self? Because wow, when you step out of it, it's still a part of you. It's not Severance—you're not split and are still the same person.

Give us a list of 3 things; you pick the topic.

Top reads

1. Measuring the user experience (For Researchers)

2. Don’t make me think (For Designers)

3. Do Artifacts Have Politics? (For All)

What is your favorite song of the moment or something you have on repeat?

I've been reconnecting back to Sade. She's an older Nigerian British singer, and she's amazing. I've been obsessed with listening to her music lately. Her albums Lovers Rock and Love Deluxe are great. I've had "I Couldn't Love You More" on repeat for a few weeks. That, and Smooth Operator, Sweetest Taboo, and Kiss of Life are just amazing.

Enjoyed the Conversation with Hope Idaewor? You can find her at www.hopetalks.design, where you can book a 1:1 mentoring session, explore her UXR courses, and sign up for her newsletter.

Hope is also passionate about giving back to Gem Fellowship.

Gem Fellowship is a fellowship program dedicated to the advancement of racial diversity in engineering degrees. A donation was made to Gem Fellowship as part of this Conversation.

You can support Gem Fellowship by donating directly.

west & ease is part of & luo studio, where I do fractional design consulting, design coaching, and host creative community events. If you’re a brand, team, or creative partner interested in collaborating, I’d love to connect. You can learn more and reach out at andluo.studio.

Meet Peter Nguyen, the New York and Austin-based founder of The Essential Man, where he helps men elevate their style and look really fucking good. Peter shares how his creative journey started with working towards an oil painting degree in San Francisco to eventually making a series of decisions that landed him at Parsons School of Design, where he studied under Tim Gunn. His career continued for over a decade in the fashion industry, including working with renowned designer Robert Geller, the current Head of Menswear at Rag & Bone. After launching a leather jacket line, he pivoted to create The Essential Man, blending his expertise in menswear design with a passion for helping men express themselves authentically. Peter shares how his diverse experiences shaped his approach to blending creativity with business strategy, the lessons he learned from trying, and the importance of connecting diverse inspirations to foster originality. Peter has built The Essential Man into a platform for inspiring transformation through small, actionable goals and a commitment to personal growth.

Interviewed in May 2024 | This conversation has been edited for clarity and brevity.

Please introduce yourself. My name is Peter Nguyen. I've been a private personal stylist for men for nine years. Before that, I was a menswear designer in New York for 11 years. I've lived in New York for about 20 years.

I originally moved [to New York] to attend Parsons [School of Design]. Tim Gunn was my mentor and the head of the department. I moved here right after the first season of Project Runway premiered. They filmed in our building on 40th Street near Times Square. It was crazy because they didn't know how big it was going to be.

Presently, I've been running a personal styling business for the last nine years. I was doing it solo up until last year. I have one employee, and it's just me and her. I primarily work with guys who are going through a big life transformation. Many of my clients have sold their company or gotten a big promotion. They may have lost a lot of weight. I have a couple of divorced clients who are looking to date again. There's always some catalyst for wanting to reach out to someone to help with their style because they're on a whole self-improvement journey or need something to kickstart it. Most of my clients are successful and have a lot of supplemental income. They have money to finally be able to work on themselves, which is pretty cool.

Let's go back to the beginning. Can you share how you started your creative journey? I originally studied fine art to be an oil painter. I went to the Academy of Art in San Francisco. I knew I wanted to do something in art because I didn't know anything else.

While I got good at oil painting, I switched to fashion later because I had a crush on a girl in the fashion department. laughing So I took a lot of fashion classes like fashion drawing and fashion theory and ended up really liking them.

My professor, Simon Ungless, who used to be on Alexander McQueen's original team, was the head of the department there, and he loved my drawings; he said, "You should think about switching over." That was the lightbulb moment when I thought, "This is really interesting now." [Simon Ungless] would spend his entire class showing us old runway photos and videos of McQueen on VHS. He would talk about all the collections. It was so fascinating to me because it was like another world.

Did he also have all the details of the behind-the-scenes? Yeah, it was really interesting because there's a famous collection from the mid-90s, '95. It was the Roadkill collection where McQueen made these beautiful garments, and they put screen printing paint on a wheel and ran over the clothes he was famous for. They pieced together dead-looking animals, and it was very controversial. Well, yes, because it makes you talk and create conversation. Yeah!

Growing up, my older sister studied fashion. My sister and mom would watch Fashion Files, and I grew up watching that, too. I saw it, but, like most people, I didn't understand it. I wondered why the dresses were so huge. Who is wearing this? Who is buying this? I didn't understand. Studying fashion gave me context, which was really fascinating. To connect the dots. I see the creativity. I can see how you can go beyond aesthetics, have a point of view, and do interesting things.

[While at Academy of Art San Francisco,] I applied to Central St. Martins in London and Parsons in New York. Central St. Martins because Ungless went there, and he said I should if I could travel. But I also applied to Parsons because it’s where Marc Jacobs went. He was really big at the time for his Louis Vuitton collection with Takashi Murakami. I got into both, but my mom said, "You're not going to England." So, as a compromise, I went to New York.

I'm surprised she was so accepting! Well, here's the thing. I have three older siblings: two older brothers and one older sister. My older sister dropped out of college, and my two brothers didn't go. So, I was the only one to go to college. They were just happy that I was doing something. All the money they saved up for college went to me, so I had no student loans, which is pretty amazing. That allowed me to leave art school three years in, even though I was so close to graduating from oil painting. When I went to Parsons, I ended up leaving my senior year.

Can you discuss the transition from the Bay Area to New York? I initially looked on Craigslist and found an apartment in the Upper West Side from this guy who had just graduated from Dartmouth and was starting a job and needed a roommate. So I got a ticket and moved to New York with a backpack, even though I had never visited before. I went straight from the airport to the apartment. I didn't even know how the trains worked.

I was 22, and it was the summer of '05. I would start school in the Fall. Before I started classes, I got a job as a styling assistant from a friend. I knew about it while interning at a magazine in San Francisco, where I did graphic design and illustration. They had worked as a stylist in New York before, so I became her assistant, which was my first experience. It's very cool how you were able to bridge the gap and leverage your network to figure out your footing in the city. It was a terrible job! As they usually are! In retrospect, it gave me insight into editorial styling that I don't think I would have ever gotten because I had gone to school for design to make stuff, so I would not have pursued or looked into styling after that.

Taking a step back, did you decide you needed a job lined up before starting school? Well, it's just one of those things where I shared, "Hey, I'm moving to New York." And then someone tells you, "so and so lives in New York." You say that casually! Only a few people find jobs along the way to something else through their network. Well, everyone knows that networking is important. But they think of it as saying, "I need a network with a stranger to get me somewhere." But people that you know probably know people. And people overlook that.

…everyone knows that networking is important. But they think of it as saying, "I need a network with a stranger to get me somewhere." But people that you know probably know people. And people overlook that.

I feel it's the same way: You have friends who probably have a huge network you're not tapping into because you're like, "I can always maybe reach out to him," rather than going to a networking event where you're there for a single purpose. It's about being open to possibilities and asking for help.

So, how did the Parson's program go? It was crazy because that was the summer after the first season of Project Runway premiered. There were around 11 or 13 sections when we entered the program. Each section would have 15 students at the most. The following year, they got so many applicants. By my junior year, there were 23 sections with 30 students each. What timing for you to join. When I think about the timing of my life, it's crazy. But you were prepared. The opportunity came, and it happened. A lot of people think it's luck. I think it's all about preparation. If you prepare yourself, you're more open to the opportunity.

A lot of my clients will ask me, "When will I ever need a suit?" Or "When will I ever need a tuxedo? I have no place to go." But if you get one, you find places to go in your nice clothes. That's the same idea where things happen if you prepare.

Were there any people or experiences during the program that helped you get excited? Oh my god, so many! The teachers at that school are so good. It's trendy to say that college isn't needed, but unless you're a hardcore self-learner, it's better than nothing. It's better than flailing because you can access other people's decades of experience, knowledge, and insights. That's something you cannot YouTube your way into.

We had a class where you learn to develop a collection. Say I want you to design a children's line for Fall/Winter—open inspiration. My professor always stressed that we need at least two sources of inspiration because if I were doing a women's collection inspired by the 20s, it would look so much like the 20s. After all, I only have one point of reference. However, originality starts coming in when I start combining multiple sources. So now, I will design a women's collection based on hip-hop from the 1920s and 1980s in New York. It will automatically be more interesting. Then I'm going to throw in some of my Vietnamese upbringing—then it's completely original. And it's also personal. Yeah! So you can apply this to everything. There are a lot of people who are so worried about being original when they're doing anything. They don't realize that once you learn the basics and add something you're interested in, it automatically becomes something original.

There are a lot of people who are so worried about being original when they're doing anything. They don't realize that once you learn the basics and add something you're interested in, it automatically becomes something original.

After deciding to leave fashion design, I thought about how I wanted to become a stylist and put myself out there. How do I do it in a way that is true to me but also helps me stand out a little bit: how do I be original? I thought about what if I was a menswear influencer without photos of myself. That was the rule. Now, I have to teach, and so I thought about going to take the things that all the influencers do, which is social media, and then combine it with the things I used to love watching when I was growing up, like Bill Nye, the Science Guy type of edutainment.

Combining these two things, what if Bill Nye was a menswear influencer? What would that look like? It's the idea of combining two things and creating something new. Because if I came in and played the influencer game, I would look like everyone else. So that was a big lesson from the program that I still use all the time.

Putting this approach into context for myself, as a product designer, often when designing, people ask, "Well, what are our competitors doing?" That feels boring to me. We're not leveraging your team's skills and talent and are only looking to one data point as inspiration.

Speaking of competitors, I don't follow any other fashion influencers. Because you could get influenced? Yes, even unintentionally, too. I follow travel bloggers and food reviewers. It also helps me combine inspiration. Okay, so what if I did this for fashion?

I'm starting a YouTube channel, and the prompt I wrote for myself when I decided to start was: what if Sofia Coppola made a YouTube channel? What would that look like? I'm doing a bit of Wong Kar Wai and Sofia Coppola film grain, and it's a little artsy. It's a little pretentious, but that's what I'm into.

Moving forward in the timeline, what happened after the program? So, I didn't graduate. I gotta backtrack a little bit because when I was still in San Francisco, I was working for that magazine. I was reading a lot of fashion articles and collections. That was my gateway or exposure to brands that weren't common for a 21-year-old dude who doesn't follow fashion. I knew Gucci, Louis Vuitton, and other name brands. But then I started discovering designers like Helmut Lang and Cloak, which are gothic and cool and look like vampires. It looked like nothing I'd ever seen.

Specifically, Cloak was started by two people from Marc Jacobs: Alexandre Plokhov and Robert Geller. It's super cool, and to me, it was like, "Oh shit! I didn't know fashion could be this way."

Fast-forward to New York. I'm in my senior year, and I saw in Women's Wear Daily that Robert Geller is starting his own line for men. I googled and emailed him, asking, "Hey, do you have any internships?" And he said, "Yeah. Come by. My office is on Bleeker and Broadway in NoHo." My first apartment was at Bleeker and Lafayette, right across the street.

So I asked, "Can I come over for lunch now?" And he responded yes. So, I walked over there, and we started bonding after I saw tickets to The Cure were pinned behind him. I grew up listening to a lot of 80s music. And so, he asked me, "When can you start?" I was like, "I'm going to start next week."

School was starting again in a month, but I decided to quit school. I got the money back from paying tuition and lived off that for a bit. That's when I quit school because I knew people spend a lot of money on their senior thesis where you'd build a collection and compete to be in the senior show.

The senior show at Parsons was legendary because Barneys and all these designer buyers and magazines would show up. In 2002, Barney's bought Proenza Schuler from their senior collection. So, the senior collection is a huge deal for a lot of people, and they would spend ten or twenty thousand dollars at that time, and now, I'm sure, hundreds of thousands of dollars on collections.

Wow, so you forgo the senior thesis to work with Robert Geller? Also, at that time, Parsons didn't have a mentor program. You do general design, and then in senior year, you would specialize. The curriculum would change every semester because they were getting so many new students and trying to shake up the whole system.

They kept trying different things, and many students who came in then were frustrated because Parsons didn't know what they were doing. I was a little annoyed with that, too. A class I loved last semester isn't around anymore because they decided to scrap it. They would make us take a history class, but it might have been more helpful to take a business or sewing class instead. All of this helped me decide to leave.

How did the internship go? I worked with [Robert Geller] for five, almost six years, and it was amazing. It was life-changing. It was a different and very rare setup. Robert Geller was a small designer who a Japanese company funded. So, he was independent of the American fashion system, which is a different beast. We could do things that most brands wouldn't be able to do. It was five or six people, including a couple of patternmakers, a couple of stylists from Japan, and then Robert, me, and the other intern, Joey.

What does it mean to be independent of the American fashion industry? Fashion, especially Menswear at the time, wasn't very interesting in America. There's a joke in fashion design that, given enough time, you end up working at Ralph Lauren, J. Crew, or Banana Republic. I've had friends who worked at all those companies. And at that level, if you go to Ralph Lauren, you'll specialize in one thing. You may do men's denim, and that's all you do. Then you have someone who specializes in knits for women. Versus Robert, Joey, and I would design everything together. We would sit down and hand draw everything while everyone was using Illustrator.

It was an amazing experience because it's like a small startup. You get to experience all the parts, as I helped on the runway shows. I would call the runway models out. I'm also painting the stage! We're doing a lot of hands-on stuff and realizing that a lot of people who have been in the industry now don't get to experience it.

That's wild. Reflecting on my experience as well, many people will never get to experience what I've experienced. My first job here in New York was at a small 30-something-person startup where I was the second designer and did a bit of everything. An early career colleague recently told me, "You sound like a product manager." My response was that it was because I was trained by product managers, and up until I joined a large company, at every startup, I was reporting to either the CEO or product leader. The big learning was that designers are more effective when they can understand the business to influence the strategy and vision and not just create visuals. Some days, I dream of being an intern again so I can go back to basics, learn from that lens, and try everything again.

It's the same thing in fashion! If you talk to any fashion person now who grew up in the Tumblr era of Menswear, most of these folks are Gen X. Robert Geller was in his thirties when he left his corporate job to start his own thing. That's why it was such an exciting time for these starting brands, like Robert Geller, Thom Browne, etc. It was exciting for Menswear because American fashion didn't have much except for hip-hop in the late '90s.

What happened after this internship? I had nowhere else to go because we were a small company and team. I can't replace Robert Geller, and so I'm stuck. He's also a small company, so he couldn't afford to bring us all in, so many of us had side jobs. For example, me and my other colleague started an online shop. I would freelance and specialize in leather jackets because I learned so much from Robert and would apply that to other places. I did a lot of ghost designing and freelancing.

Ghost designing is similar to ghostwriting. A celebrity launches a brand, but most of the time, they won't actually be designing. Instead, they hire a team and take the credit—which is fine. I did a lot of that. But it got to a point where I thought maybe I wanted to start my own thing.

I had a good amount of savings, so I started a leather jacket company. I didn't know what I was doing. It's really expensive to make things in New York and pay a living wage to people while using high-quality materials. You're sourcing everything and paying for shipping, inventory, a warehouse, and raw materials.

I didn't have enough capital to buy leather in bulk, so I'm paying near retail price, which is insane. It got so expensive that I burned through my savings in two collections. In retrospect, learning what I know now and talking to people with brands, they're like, "Yes, of course, you need at least a couple million." Many people who start their brands first work in corporate in their 20s and 30s and then in their 40s and 50s start their lines because it's impossible to get funding. So, I blew through my savings and didn't know what I wanted to do next.

Was that a year or two with the two collections? Yes, I had my line for about a year and a half. I sold a few, but not enough to pay rent, and I was living off my savings and credit cards and borrowing money from my wife, who was my girlfriend at the time. She was super supportive and awesome, but it was a really stressful time for sure.

It sounded like you had a proof of concept, and then the concept went to launch, but you needed more to continue pushing. Yeah. I've always been good at selling, but I didn't know enough about business to think about cash flow, etc.

So, how does The Essential Man come in? The Essential Man used to be my Tumblr blog. It was where I would write and show behind the scenes of fashion in New York, my life, and just things I was into.

I had also been following this personal finance guy named Ramit Sethi for a few years. Ramit had a course called "Zero to Launch," which is about creating a business using your knowledge or skills. I took that course and followed it to a T, and the whole point was that you find something good that you can monetize and how to test and validate a business idea around that.

So, I brainstormed a business idea around what I could do, like teaching people how to be designers, or styling, and how to shop. I did some research and saw people advertise. I talked to my friends who happened to be in tech, and one guy hired me for a conference. That's how it snowballed from there.

Some people feel that they need to show credibility when they start something. Did you feel the same way? My credibility came from being in fashion and dressing cool—that and having gone to Parsons. I have been a menswear designer for over a decade and can help you pick an outfit.

With credibility, you already have the confidence to do it. Was there anything that you learned along the way that helped you push it even further? Yes, so I always thought the worst-case scenario was that I could get a corporate job. Or that I would work at Starbucks. I knew that rock bottom wasn't possible and that there were other careers I could have until I figured it out.

You say it so simply! laughing With many of the conversations I have with my friends, we're always so fearful about what happens next. Some of us, especially in corporate jobs, end up in golden handcuffs even if we know we can leave and try something new. But the risk and time it takes to go into the next phase of our lives also takes a lot. But to you, you're just like, "Oh, cool!" I'll tell you why. My parents have always started businesses when I was young. I learned from them that you can figure it out. It's sometimes easy to forget that my parents escaped a war. My mom's first job was as a hotel maid, then worked at Burger King and figured it out.

We often forget that it's not the end of the world. Rock bottom is almost like a joke because did you die? Because no, you didn't die. I understand the fear of everything going to shit, but if you really sat down and listed out that if this happens, I can do this, and you can keep going forever until you get to the point where there's nothing left. The other part is reminding ourselves that we're highly capable and that it takes more effort to fail.

Rock bottom is almost like a joke because did you die? Because no, you didn't die. I understand the fear of everything going to shit, but if you really sat down and listed out that if this happens, I can do this, and you can keep going forever until you get to the point where there's nothing left.

To the point of how things take a long time: The advantage of being older is that you understand how long things take, so you take your time. For example, the YouTube channel I'm starting: I don't want it to begin to blow up, but I know that in two or three years, it will be killer. Because when you're young, you haven't lived enough. And you need to live longer to know that things will eventually work, and they can work out. For example, you go through a few breakups, get fired a few times, move a few apartments, and things will be fine five or six years later because that's what experience is. You have the context, and that's why failing when you're younger is scarier than when you're older. Yes, you have no clue yet! It took me nine years to get to where I am, and I can do it in another nine years.

Because when you're young, you haven't lived enough. And you need to live longer to know that things will eventually work, and they can work out.

I recently guest lectured with a friend at my alma mater to talk to design students about our careers journeys. My friend, Triệu Thanh Nguyệt, shared that we need more data points to make better conclusions or arguments for the next thing. That and you don't need to have all the answers to make a firm decision. Additionally, earlier in our lives, we hear a lot from everyone else around us about how they've made choices, what they wanted to do, or how they got to where they are. We don't realize that it's an accumulation of many choices, and nothing was ever that final. If things are meant to be, I also believe you'll find your back to it. You're more capable than you think.

Were there more learnings you experienced when you started your styling journey? Whenever I start something new, I set goals. My first goal with the styling business was to book three clients because one is a favor, two is lucky, and three is a pattern. I do that with anything when I start. For example, I will focus on three YouTube shorts, and if the first or second one gets some views, then it's okay. But if I do three or four more videos and no one is watching, maybe something's off here.

So far, I've posted a few videos, and they've been killing it. So, it's already given me the confidence to repeat. Whenever I try to test something new, for example, I'll go to three pottery classes and see how I like it. It's a small investment, and it's still low, and it's enough for you to get the data points that you need.

Out of everything you've done so far, why is any of this important to you? Every phase is something new. Initially, it's been about "what's interesting to me?" And then, as I get older, it's more, "How can I help more people?" or "How can I affect certain things?"

Fashion is interesting because it's a creative and artistic business that is still commercial and functional. If I weren't in this industry, I would probably be in food, interior design, or something artistic, creative, and functional. That's what attracts me to styling "regular guys" rather than editorial or celebrities. I have to think of them in the context of their lives, interests, and more.

It's a creative challenge, and I get the artistic aspect of where I get to dictate what that looks like. I always tell my clients that they are characters in a movie, and it's my job to figure out the costumes for their characters. I'll ask them, "What's on your Spotify playlist? What kind of movies are you watching? Where are you guys going if you and your wife go out?"

That's fun for me, but helping people is my whole thing. I always wanted to be the [Anthony] Bourdain for men's fashion where he's showing you all this cool shit, but also he's showing you that food is culture the same way clothing is culture. Sometimes, we think it's frivolous or purely functional, but it's integral to who we are and our expression. It is essential to show guys that fashion is fun and that you don't have to be super nerdy to be in it. But at least you can appreciate things about it and be interested and be a more interesting person through it.

Are there any misconceptions about the work you do, the industry you're in, or yourself? A lot of people think fashion people are snobby. Whenever I'm at a party, and someone finds out I'm a personal stylist, they'll ask me, "I don't want you to judge me or what I'm wearing." They're judging themselves. I get it! But I always joke to them that, "I only judge people who pay me."

First of all, that's completely true. Don't do anything for free that you can get paid for. Fashion gets this snobby, pretentious rap, and it is in some aspects. However, there is a good kind of snobby that I find fun. People are scared to investigate the fashion world or be interested in fashion because they believe everyone's snobby, but most people aren't.

And the good people are good snobby. A bad snob makes you feel bad about your choices—like what you would think a fashion person is like in a movie. Bad snobby is when someone says, "Ew, you're wearing that?" or "Ew, you're eating that?"

I know what you mean by good snobby. It's the people who are passionate about how they dress, what they put on their bodies, and how things are made. It's more about the care they have versus a projection of themselves cast as judgment to others. They care about the thing or topic itself. I think of myself as the older brother who goes to school in Europe, and I'm back in town for a week. I'm like, "mom and dad are out, I'm going to show you some cool shit."

With my clients, whenever I recommend something to someone, I learn early on instead of saying, "Don't wear those; those are ugly." I would say, "I think you're the type who would wear Loewe. You're a Loewe girl." Now, suddenly, you're like, "What does that mean? He sees me as something, and I can be a little different. I should investigate this."

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So that's a good kind of snobby where if I was your brother and I came home from college, and I say, I'm going to show you a cool drink I had in Paris and say, "It's the craziest shit!" That's what [Anthony] Bourdain does. He'll say, "Let's go to Vietnam," and show you the little stools, the little carts, and a place that makes the best bowl of pho ever. Now you want to go. And that's the fun snobby that is missing a lot of the time. It's also a way of creating an inviting atmosphere, encouraging someone to be part of the experience rather than casting judgment or bullying. Sometimes, snobbiness can come across as making something exclusive and incomprehensible.

Yes, to be fair, fashion that gets presented online or, in general, is that bad snobby because that's what people think. It's almost cliche, but if you are talking to anyone like Cathy Horyn, Anna Wintour, or really respected fashion writers or editors, people respect them because they are not the bad snobby. They're the fun snobby.

A perfect example of a fun snob is Rajiv Surendra. Rajiv played Kevin in Mean Girls. He quit Hollywood to become a calligrapher and does all the signs in restaurants in New York. He also has an amazing YouTube channel where he'll show you how to wash your linens and wrap a gift. He's like the male Martha Stewart; all the videos are in a beautiful film grain. He has the most fascinating life, and it's so aspirational and snobby, like he goes to Europe to find tweed to make a jacket! But that's the thing that is missing in most spaces.

Do you have any advice for a younger Peter? I don't have any advice because I love where I've gotten and feel if I had advice for my younger self, it would change my trajectory, which sounds like a cop-out answer!

But it may be better not to work so hard. I'm at a point where I've worked with many ultra-successful people. Right now, I have a client worth nine figures, which is mind-blowing. I've seen the ultra-wealthy in many ways that most people don't get access to, and nothing's changed. Just a little more zeros at the end! They have bigger places, but I've also seen shitty marriages. I've seen people stressed out and constantly working while shopping, and ultimately, people are all the same.

My wife and I talk about our finances a lot, our goals, and stuff we want to save for. I've sat and reflected that we lived a good life. New York for 20 years is insane. We've had multiple apartments; we lived in a new building with a doorman. I can buy whatever I want relatively. I take Uber a lot because of work.

I'm grateful for where I am, but I don't know if I need to work too hard. I have no aspirations of being a billionaire or running a multi-million dollar company. At the same time, money is an important aspect of our society. But I've gotten calmer as I've gotten older, and I wish my younger self could feel this way. I'm just very chill.

Because when you're young, you're told you gotta work hard, gotta hustle, and all that stuff. You're told what other people's aspirations are because you have yet to form your own. You wouldn't believe how many of my clients I've talked to wish they had smaller companies, who wish they had more time, who complain about back pain, or who complain about money. It's all the same shit.

A lot of folks who are anti-hustle culture have experienced hustling very hard. As you get older, and the more you ask for help and open yourself up to other things, you also welcome a lot more of other people's aspirations and thoughts. The hardest part for an individual is to decide at what point "this is actually my path."

Give us a list of 3 things; you pick the topic.

1. Herman Miller Aeron chair. It's so worth it.

2. Get good cashmere is always nice!

3. Get stationery from Terrapin Stationers. I believe in writing thank you notes because I think no one does it anymore, so you stand out easily.

Here's a little trick I'll teach you. To get VIP treatment at clothing stores but basically anywhere: whenever I go to a new store, and I work with a client or meet the person, afterward, I always come back and give the staff a thank you note and some Levain cookies or something similar so that they'll always remember me. It's so easy, and it'll only cost a couple of dollars. It's all about building relationships and getting the habit of doing things to do them. Yes, you can send an email, but something about writing a note and giving it to someone is so nice.

What is your favorite song of the moment or something you currently have on repeat?

Whenever I'm in New York, I listen to Frank Ocean, specifically Channel Orange or Pink and White. It came out at a time when I remember always just listening to it while I was walking around. I also listen to a lot of hip hop, jazzy lo-fi, and J Dilla. which all feel very New York to me.

Enjoyed the Conversation with Peter Nguyen?

You can find him at www.theessentialman.com, and @theessentialman on Instagram, Tiktok, and Youtube. Peter also offers styling in-person and virtually with more information at https://www.theessentialman.com/styling-services.

Peter is also passionate about giving back to The Trevor Project.

The Trevor Project is an American nonprofit organization focused on suicide prevention efforts among lesbian, gay, bisexual, transgender, queer, and questioning youth; they offer a toll-free telephone number where confidential assistance is provided by trained counselors. A donation was made to The Trevor Project as part of this Conversation.

You can support The Trevor Project by donating directly.

Meet , co-founder of Versive, an AI-powered user research platform that helps companies conduct and analyze research faster. Eric started his career in finance, transitioned to design, tried out product management, and eventually founded his own company. He shares with us how he approached exploring new careers, building new skills, and what he learned along the way in each role through the lens of solving creative problems for people by building for them and their needs. 

Interviewed on March 2024 |  This conversation has been edited for clarity and brevity.

Tell us a little about yourself—who you are and what you want the audience to know. I'm Eric, co-founder of Versive. We're a user research tool that uses AI to help people conduct and analyze research faster.

As far as careers go, I've gone through a lot of different twists and turns. I started working in investment banking and then pivoted into becoming a designer, with some stints as a product manager in between. Then, ultimately started Versive, which also had its twists and turns.

I grew up in the Chicago suburbs. I've been in New York for over ten years and live in Brooklyn with my wife, Emily, and my cat, Mochi.

Let's start at the beginning of those twists and turns. Could you share how you started in finance and where design came from? In high school, I did all the school stuff I was “supposed to” but was also interested in art and painting, which I always thought of as a hobby. But I really enjoyed it; it was a small part of my identity.  When I went to college at the University of Chicago, there was almost no trace of any design program [at the time]. I met some friends who were also interested in art and design. We knew people starting nonprofits, student organizations, and companies, and no one knew anything about design. People needed to create logos, marketing materials, and websites. There was a problem people needed to solve, which seemed interesting, so I decided to try to solve it for people.

But then, I also spent a lot of time trying to get good grades in my econ classes and joining business-related clubs. In junior year, everyone started recruiting for investment banking and consulting jobs. I realized this is the game everyone plays, so I decided to play as well and see if I could get a good job at the top firm. I did it because I didn't know what else to do, and it seemed like a safe path. If I were to go back in time, I wouldn't have done that [route].

Why not? It was less, "I'm super passionate about this," but more, "This is a thing that is good for me, and if I do it, I'll have a good career, and people will be happy with me." While it was interesting, I liked solving more creative problems but didn't know I could make a career out of it.

What happened as you went from designing for fun to pursuing a career in finance? What did you end up doing, and what were some of your learnings? My ultimate goal was to get a job in investment banking. I did an internship that turned into a full-time offer with JP Morgan in their Tech, Media & Telecom investment banking group in New York.

Typically, you're supposed to work in banking for two to three years. Then, most people will go into a private equity or corporate finance job at a big company. I ended up staying for only a year and a half—up to my first bonus.

Overall, it was a good experience. I made some good friends because you're working in your little cubicle with other people who just graduated from college. You're there for 80-100 hours a week, and you see these people more than anyone else.

I also learned how pointless a job can feel and how many hours you can still put into it. Maybe I also improved my work ethic. After having [worked in investment banking], every job after seems much more chill, especially after moving to tech.

What factors did you consider to help you decide to move out of finance? Investment banking is a job that provides services to other businesses. Most of the job involves pitching and selling to companies to "Use us to do your M&A or raise money." You're trying to sell the customer what they want to hear and help them facilitate the transaction. It adds some value, but that wasn't what I wanted to do. I wanted to find a job where I was actually building something for people and solving their problems.

So I didn't like the job I had, but I also didn’t like the job I would have next. In investment banking, you start recruiting for your next job after six or seven months when you barely know your current job.  If you get an offer, you basically work in banking for another year and a half before starting the next job. I did exactly that and got a job at a pretty good private equity firm. I went to their welcome event, and everyone was making jokes about how they hated the job. And I'm like, "I don't know if I want to do this either."

Most importantly, I was in a long-distance relationship with my girlfriend, now my wife, who was still in Chicago. I wanted to be in person with her. I had this job that I didn't really care about, and I wondered if there was a way I could quit my job and move to Chicago.

Out of nowhere, an opportunity fell in my lap. I had a friend who ran the product and analytics team at Sears, the big retail company, and he was hiring for a role on their strategy team in Chicago. I interviewed with them and decided to take the position, quit my job, and move to Chicago. It was all very quick and impulsive, but it was also a very clear-cut decision.

What happened next? Working at Sears was fun, chaotic, challenging, and frustrating all at once. It also led me to discover that I wanted to become a product designer.

In my new role, I started as an internal consultant working with different teams to use data and new products to grow our loyalty programs and encourage customers to spend more money with Sears. My boss was a 20-something Senior Vice President (SVP) who reported directly to the CEO, a hedge fund manager who bought Sears and merged it with Kmart. It was a weird situation because I knew nothing, and I was supposed to tell all these people who had been working at Sears for 20-30 years what to do, give them advice, and work with them on projects.

Our CEO wanted to do a lot of product experimentation with social commerce and our loyalty programs. He acquired a company in Israel that was trying to build a social shopping website. I flew to Tel Aviv every month to work with them and got my first exposure to the world of product managers, designers, and engineers. Eventually, my boss let me build my own team focused on launching 0 to 1 products for our loyalty program. Looking back now, I was not very good at my job, but I learned a ton.

I especially loved working with designers.  Product design was the perfect combination of my creative and logical sides. I loved that it combined visual design, problem-solving, and business strategy. This was the moment I realized, "I want to be a designer."

How did you make the move into design? I wanted to get a design job outside of Sears at a more tech-centric company. I started applying to jobs but heard back from almost none of them. When you don't have real experience and are trying to get your first job, it's really hard to get your foot in the door.

I started reading design newsletters and listening to podcasts to try to better understand the industry. I also figured I would need to build a portfolio of work, so I tried two things.

First, I started making design a bigger part of my job since our team was short on designers. I started not only writing product requirements but also creating mockups—first building wireframes in PowerPoint before eventually using Sketch to design full high-fidelity flows.

Second, I started working on a creative project with my friend, Alex. When we traveled for work and fun, we were inspired by the cool local fabrics we saw at markets around the world. So, we started a fashion brand where we made men’s button-down shirts out of interesting fabrics that we found in Japan. While it never became a real business, we sold tens of thousands of dollars of shirts, and I designed and built a website that made it into my portfolio. 

With a scrappy portfolio of real projects, I applied to many more jobs and got a few interviews, leading to two or three final rounds. I ultimately landed a job at a small startup called Capture, building products to help companies like CNN and Buzzfeed search for real-time social content on platforms like Instagram and Twitter. The team liked my work and took a chance on me, and I’m still grateful for the opportunity.

I became the only designer in a 5-10-person company, working closely with the CEO and engineers in a small office in Soho—it was a great experience. We didn't follow the “proper” design processes or do a lot of research, but we shipped a ton of work. I only worked there for 6-7 months before we were acquired, but during that time, we redesigned the entire app and designed a brand-new product, which was great for learning.

So what happened after Capture? When we were acquired, it wasn’t a meaningful outcome for me as an employee, and I didn't want to join the acquirer, so I started looking to join a better-funded startup where I felt like I could grow with the company. After interviewing at a few companies, I landed at Bread, a small startup that helped retailers offer pay-over-time plans to their customers. I joined as the first designer when the company was less than 20 people, and it grew to around 200 while I was there.

It was really cool to see a startup grow and become a real business. I grew a lot as a designer there, shipping lots of new features, leading a rebrand, helping to hire product managers and designers, and setting up our first research processes. 

Bread was also a great training ground for my current role as a founder. The cool thing about being at an early-stage startup is that you get to see everything. For example, you're talking directly with salespeople, sitting right next to your engineers, and overhearing the customer support calls. You're also not bound by your job description. I set up our product analytics, wrote the front-end code for our dashboard redesign, and helped put together our fundraising decks. My experience at Bread was a preview of what I'm doing now as a founder. It’s not the same as being responsible for everything, but it was probably one of the best ways to learn.

Oh, and I also got to work with some fantastic people, including my current co-founder, David, who was one of the first engineers.

My experience at Bread was a preview of what I'm doing now as a founder. It’s not the same as being responsible for everything, but it was probably one of the best ways to learn.

Since college, you've always had something tangentially related going on in your path. During this stage of focusing on your design career, did you also focus on something else? No, I don't think so. This was a period where I was very satisfied. I liked my job and was still being challenged. I also found fulfillment in my personal life. I got married to my wife Emily when I was at Bread. 

So you transitioned from a small company to a large one and transitioned out of that after. What spurred that decision? I really enjoyed working for a startup, but I still wanted to work at a top company, one that was known for design. At Capture and Bread, I was good at my job but part of me always wondered if I was a good designer. Maybe it was because I was self-taught and never had a design education, but I wanted to work with other designers and get some validation so I would be able to say, "I know what I'm doing" 

After Bread, I was lucky enough to get a job at Uber. Uber Eats was actually the top company I wanted to work at. I remember reading a blog post about how the team did research around the world, and I thought, "Oh, that's so cool.” It's like you're designing not only an app but also the real-world interactions.

My number one takeaway at Uber was that it’s a lot of fun to work in a team with other designers who all understand each other. I made some good friends and worked with some talented people. The second was that the work itself wasn’t that different from my time at Bread, but you end up spending more time on things other than design. There’s a bigger focus on process and building consensus, but I felt like I could get good at it if I put in the time. Still, it was a little frustrating to be moving so slowly and needing to spend so much time advocating for projects and being okay with your team’s ideas not always being implemented. I definitely worked on some projects that didn’t ship until a year or two after I left the company.

There are pros and cons to working at a big company, but it was also really cool to work on something at scale and ship experiences to hundreds of thousands or millions of people and see whether they work.

What drew you back to a smaller startup after your time at a big company?  The first year at Uber was great. The company was growing, and the world was very happy in 2019. We got to do a lot of traveling for some really interesting research projects.

But then Covid hit and everyone started working from home and the company went through layoffs. Luckily, I wasn’t affected, but it made me reevaluate what I wanted in my job. I missed the autonomy and ownership I had at Bread and Capture and I wanted fewer Zoom meetings and more doing.

I wanted to start my own company, but I wasn’t sure if I was ready to do it right away. I didn’t have a compelling idea, and there wasn't someone I wanted to work with. So, I decided to find a very early-stage startup to see if I could get paid to help someone else build a product from scratch.

I got in touch with Kat and Lalit, the founders of Vareto. They were trying to build a modern FP&A (financial planning and analysis) platform. Many designers might say, "That's not a very exciting problem." But, coming from the finance world, this felt like a great fit for me. It's probably not a problem I would solve on my own, but it's an interesting problem that I was uniquely able to work on.

How did Vareto compare to your other startup experiences?  So, I joined Vareto as a designer right after they raised a seed round on an idea with no product built yet. There were about five of us, and it was really fun to design the brand, set up the design system, and design all of our initial products from scratch. I joined almost every customer and sales call. It felt much earlier stage than Bread and with some experience under my belt, I felt like I could make decisions with more confidence. Because there were no PMs, I ended up basically being the PM. I talked to customers, designed the solution, and then ran the planning meetings with engineers.

I had stepped in and out of the PM role at Bread, but this time I wanted to give it my focus. Kat and Lalit were very supportive and let me hire a designer so I could transition into leading product. 

What was it like? As designers, we often get frustrated with PMs, they control the roadmap and make all the important decisions, and they’re always telling us what to do. After being a PM myself, I definitely developed more empathy. It's really hard to be a PM. It's so much work, and with the power comes a lot of responsibility. You have to be on top of all the engineers' work to make sure they are unblocked and shipping bug-free features. You have to know what customers and prospects are saying, turn that into a roadmap,  and make sure your designers and engineers have the right amount of context to know how to move forward.

It was especially challenging at a startup working on a niche problem where everything is undefined, and none of the engineers or designers has really “lived” the role of the customer. It also sparked this thinking that if I'm doing this really hard job where I have to be responsible for a little bit of everything...maybe it's time for me to do that for my own company. It also made me realize that if I ever went back to working for someone, I would probably want to be a designer. That was the sweet spot for me after going through all of these different iterations.

So, from Vareto, how did you and David get started? David and I have wanted to start a company together since we were at Bread. When I was at Vareto, and he was at Google, we started talking about ideas we wanted to pursue. The one we were most excited about was building a more interactive way for people to learn how to code and for instructors to build courses.

I was open with my boss, Kat, that I wanted to work on my own startup. I probably wouldn’t have done this at any other company, so huge credit to her for building a culture where I felt I could be completely honest. I told her that I wanted to start a company and go full-time on it in a few months. She was incredibly supportive throughout the transition period and even ended up investing in us. 

And so, we had this multi-month period where David and I were both working at our jobs and slowly working on a prototype on the side. 

The real forcing function was when we realized that Y Combinator had a deadline for their next batch in a week and we decided to apply. A week! I remember it being very short! Yeah, this was where I was like, "Okay, this week I'm winding down from my job, and there's no urgency on the startup yet. I'm going to visit a bunch of museums." But then that all changed. When we got in, it became real. We needed to move quickly on this. And we need to make a lot of progress because there were all of these deadlines. The application, the interview, and then YC started in January with a demo day and fundraising in March.

What were some learnings or interesting moments that brought you to where you are today? I can't believe it's been basically a year! It feels like it's been three or four years.

The biggest learning is that it's really hard to build a company from nothing, especially getting people to pay to use what you're building. We went into YC to build this marketplace for programming courses and built a pretty powerful product. We're pretty good at designing and building, but the hard part for us is selling and getting people to use [the product]. We're not naturally self-promoting or super extroverted people.

One of the most valuable things about YC is that you’re building alongside a bunch of talented and ambitious people and you see what success looks like and how fast everyone else is growing. It's a good kind of peer pressure where you're like, okay, we're clearly not moving as fast as the best people, what can we do differently?

This helped us realize that programming education wasn’t the right problem for us to solve—it’s a very competitive industry and we weren’t the best team for it. So, we made our first pivot. We took our technology and shifted the focus to helping companies building technical products like APIs create better demos for sales and marketing. We got our first customer within a week, raised a small amount of money. From there we hired our first engineer, Gerardo, and went head down into building our product. 

Again, we built a product that we were proud of, but sales went much slower than we wanted. More importantly, we realized that this was a problem we stumbled on and not one that we were passionate about or had any expertise in. We were too reactive with our first pivot, so this time, we thought more deeply about what to do next.

We started from scratch and started thinking about what interesting problems we were uniquely equipped to solve. We threw out a bunch of ideas, with a rough thesis that AI was going to enable products that weren’t possible in the past. When you entered YC, AI was gaining traction in the industry. Yeah, in our batch of YC, a meaningful percent of companies focused on AI, but the next batch was almost completely AI. GPT-4 came out at the end of our batch.

One idea that quickly bubbled to the top of my list was that user research is very time-consuming. I had actually written down this problem in multiple notebooks over the years. 

You and I have done a ton of research at big and small companies and it’s always a challenge. Yes! First, companies don't do enough research and often skip the step because it takes up too much time. If you actually want to test prototypes with a customer or do some foundational research before writing a PRD, it takes weeks because you need to find people, schedule interviews, have a bunch of 30-minute conversations over multiple weeks, and then read through all these transcripts to pull out all the insights. 

When I faced this problem in the past, I didn’t have an idea for how to solve it. But, with what language models like GPT-4 are good at, it became obvious to me that this was the right time. AI could turn surveys into rich user conversations, and do the analysis for you in minutes. 

It became my obsession and I wouldn't shut up about it! laughing, David and I would be talking about our old product, and I'd be like, "Oh, what about this? Here's an article I found on user research."

It was obvious to you and you started sharing on Linkedin and with your network connections. People started contacting you because they wanted to have these conversations—especially folks in the design and research worlds because we know this is a big problem. Could you talk a little bit about how you approached connecting with your community and how that brought you to the current version of Versive?

Posting on Linkedin and reaching out to people in the industry was really useful. When we started, we talked to dozens of people: researchers, designers, marketers, PMs. People from three-person to 10,000-person companies across all industries. Every company is trying to understand their customers in some way.

We started off working with startups because they were the most open to trying a new product. We built an MVP that allowed users to create a conversational survey where the AI would ask dynamic probing questions. We convinced a bunch of startups to use our product to launch real studies. We learned that the frequency of research for smaller startups was too low for them to pay to use the tool so we moved onto trying to build a more robust platform for larger customers. If you're in a thousand-person company, you have multiple pods constantly trying to understand customers. Employees have less context and understanding customers becomes harder but also more important

We signed our first paying design partners and worked with them to build out tons of new features. We shipped AI analysis tools, a better study builder, more question types, voice interviews, usability testing, question logic, and dozens of other big features. And that’s about where we are now. We’ve brought on some name-brand customers and we’re working with them to continue to evolve the product. 

Now that you're at this stage of your career and life, do you feel like you were able to draw from previous experience or pull something from your toolkit to help you grow? And on the flip side, what are new things you're trying to learn or something that you're experiencing for the first time?

On the first question: yes, a little bit of everything. Ultimately, I'm solving this problem because it was a problem that I faced in my previous roles. That helps a lot when you're working on a startup. I can make better and faster decisions because I have more context and intuition.

I think being a designer and, in particular, working at startups has helped too. To start a software company you need to be able to do things: build the product and get people to use it. Being a designer helps you design a better product, but that alone is not enough. You also need to understand the business, figure out how to sell and market what you’re building, solve the thousands of operational problems that come up, and ideally also be able to pitch in on writing code. Working at startups has made me comfortable with ambiguity and learning on the fly.

On the second question, almost everything is new. David and I have to make every single decision, there’s nobody to delegate to. If I want to move things forward, I have to figure out how to do it myself. I’ve become a much better programmer because writing code is the ultimate way to improve the product. I went from barely understanding Javascript to shipping tens of thousands of lines of code in the last year. Some weeks, I spent 50-60 hours writing code. Thank god for ChatGPT.

Also, I was exposed to different roles like Sales and Marketing at startups but unless you've done the job full time, it's not the same. I've sat in on sales calls, but when you actually have to take the sales call yourself and be willing to be uncomfortable and ask questions, present prices, and ask for commitments, that's hard, and that's new for me. The other thing that's really new for me is putting myself out there because if it were up to me, I would just stay in my room and write code. I wouldn't be posting on Linkedin for fun to build a following, but it’s really important for the business.

Overall, this is definitely the hardest job I've done, where I've had the most self-doubt because I'm still not good at it. And the ceiling for being good is very high. That’s scary but also very exciting.

What are you most excited for next? The story for Versive is still being written. I'm very optimistic about how things are going. Things are moving faster than before, and it feels right. We're excited about two main things. The first is that we still need to build a lot for the product. We have a big vision and want to build the next big customer research platform, like Qualtrics or UserTesting and there’s a lot of exciting work to do to get there. 

Secondly, we started working with small teams. They were happy with us, but not all were willing to pay. We've shifted towards starting to work with larger companies, and we’re now working with companies we admire that have thousands of employees. And we're really excited to see where that goes. Going forward, It'll be my focus to figure out how we bring on more of these large customers and make them successful. It’s exciting and daunting at the same time.

Why does any of this matter to you—from all your decisions in your personal life and career? Well, we have to work, or at least I do. You spend a lot of time and mental energy working, and in an ideal world, the work is interesting. And you're working on something that you want to solve or teaches you new things. That it's fun and engaging. And that's something I learned about myself: that when I leave a job, it's because I get bored and don’t find fulfillment.

So now, with starting a company, I see this as an experiment I’ve wanted to try for a long time. I have something that I want to put out there that solves a problem—one that I've experienced. While it's not saving lives or anything, [being a founder] is the most interesting and fulfilling thing I've done. I'm creating something from scratch and solving a real problem for people. I'm learning way more than I ever have learned, and at the end of the day, I'm doing this for myself. I'm not answering to anyone other than customers.

…[being a founder] is the most interesting and fulfilling thing I've done. I'm creating something from scratch and solving a real problem for people.

And at the same time, when you're working at or on your own startup, you definitely have less time for your personal life. But I think you can still make time for it by cutting out other things in your life that are not valuable. I still make time for things like spending time with my wife, friends, and cat. With Mochi! Yes, and I want to pursue my hobbies like climbing and running and I’ve found that I can still make time, even in my most productive weeks at work.

Are there any misconceptions about you, the work you do, or the industry you're in? A couple of things. When you have a job, people tend to put you in a bucket. People assumed that finance people are analytical and obsessed with making money. That they only care about these things. And then, when you're a designer, people assume you just care about the creative side of things. You only think about the user and don't understand the business. But, there's a lot of fluidity in people's careers. We both know a lot of people who've done all kinds of different things. If you're in a career and you're feeling like this isn't for you, you can switch.

…there's a lot of fluidity in people's careers. We both know a lot of people who've done all kinds of different things. If you're in a career and you're feeling like this isn't for you, you can switch.

Another misconception is that in startups, I feel like you hear a lot of extreme opinions. Like, "Oh, I can never start a company because it's so much work”  or “it must be nice starting your own company where you don't have to answer to anyone." The truth is more nuanced. I definitely work more than I used to, but I still have time for my personal life. I don't always feel overwhelmed or burnt out. And yes, I have a lot of freedom, but I also feel a lot more personal responsibility. In some ways, it's just another job with its own pros and cons that many people should consider.

There's fluidity in careers but also in the focus on different problems. Even the misconception of time, which is how much time you're spending versus how much your focus is on work versus personal, is all gray. It sounds like you're advocating for the fact that there's a lot in the in-between. Ultimately, it's really how you put those pieces together and decide where or what you want to pursue. I agree with that; maybe the overarching thing is that there's no one way to do things. Often, people ask, "What's the right way to do this?" or "How do I optimize my career?" But having done all these different types of work at different companies and roles, I don't think there's a right way to do things. It's perfectly valid to be working in a big tech job that is paying really well, and you spend your time on other parts of your life. It’s also perfectly valid to pursue something you’re passionate about with all of your waking hours. It just depends on where you are, your priorities, and something that you should reevaluate all the time.

I love that answer because we realize there is no right answer as we age. When we’re younger, we look to more experienced people to tell us what to do. But the moment we realize that no one can tell us what to do and that we must make that decision ourselves because the decision is in our hands at the end of the day. And it's all about trying. Whatever you try, let's just do it—and that's been a recent learning for me. 

When you're younger, you think of time differently. Everything is like a rush, and you're a bit more judgemental when you say, "Oh, I don't want to be where this person is at age 35, right?" And you're like, "I want to be here instead!" or "Why is this person doing this with their time?" And it's now like you appreciate where you are, the decisions everyone has made, the journeys people have taken, and you understand why people took these paths. I don't think there is a right answer.

…you appreciate where you are, the decisions everyone has made, the journeys people have taken, and you understand why people took these paths. I don't think there is a right answer.

I wouldn't have expected to be doing this when I graduated from college. Yup, you would have been in private equity! And I would have a lot more wrinkles and gray hair. laughing

If you could pick an Eric at any point in time in the past, what advice would you give him? I'd probably go back to high school or college. I would encourage myself to pursue things I was interested in more seriously, regardless of whether they were "the right things" everyone else was trying to do.

When I was younger, it took me a while to figure out that I was interested in art, so maybe I should have pursued that more by taking classes in school, building out a portfolio, and going to a design program. Or maybe, in college, I should have looked into spending all my time on entrepreneurial and design-related things. 

Give us a list of 3 things you'd recommend. You choose the topic.

1. Libby the Library app or libraries in general. A lot of US cities use this app called Libby, which lets you rent books. I use audiobooks the most, and I started using this app around Thanksgiving. I hadn't read any books in the past two years, but I've read eight or nine books in the last couple of months.

2. Get a smart oven! A smart countertop convection oven changes the way we cook. Big ovens take 30 minutes to heat up, but these take two to three minutes. It cooks things faster and doesn't make your entire apartment hot. You could literally bake a chicken for lunch if you wanted to.

3. Use AI tools to make your job and life easier. Use ChatGPT and Claude. Use it to negotiate your rent like Leslie did! Or use it to write code or learn something new. It's been one of those things that has saved me so much time. It gives you specific answers and doesn't require you to read Stack Overflow threads for 20 minutes just to answer a question.

What is your favorite or current song you have on repeat?

Please Please Please by Sabrina Carpenter

Enjoyed the Conversation with Eric Li? Learn more about Eric's company, Versive, a faster, more effective way to conduct AI-powered user research at versive.com. You can also find him on Linkedin.

Eric is also passionate about giving back to Animal Care Centers of NYC

Animal Care Centers of NYC (ACC) is a New York-based non-profit working to ensure that stray and surrendered pets have access to food, shelter, and medical care as they wait to find a loving home. A donation was made to Animal Care Centers of NYC as part of this Conversation.

You can support Animal Care Centers of NYC by donating directly and consider adopting or fostering a furry friend.

Meet Abi Garapati, née Suresh, a human living and loving life in New York City. Driven by fostering community, Abi co-hosts Olive Tree Writing Club, a weekly writing community for writers of all experiences. In this conversation, she shares how her immense curiosity and deep passion for community was fostered by a pivotal time living abroad in Rome, Italy, before entering the full-time workforce, which fundamentally shifted and changed how she now approaches navigating and balancing the American ideal of striving for success. While she doesn't claim to have figured out the "right path," she's enjoying the experience of exploring and learning about herself and the world through lived experience. 

Interviewed on December 2023 | This conversation has been edited for clarity and brevity.

Introduce yourself and tell the audience what you want them to know about you. I'm Abi. I'm an eclectic mixed bag of a person. I recently discovered that the world is really big in the last year, so I am having a moment where I don't have an identity, but everything is my identity. It's been a really fun, cool time of random stuff. I want people to know I try everything, am open to everything, and love learning new things.

What things have you loved learning recently or just had fun doing? I run a writing club, and I'm obsessed with it. It's called Olive Tree Writing Club. We meet every week on Wednesdays at 7 PM in SoHo. And it has changed my life. I started as an attendee and became a co-host with my friend James. It's been incredible to see how it's grown, so that's a big part of my identity. 

I also recently revamped my blog called Verbinding. I've recently started learning to sketch, paint, and make video games. I don't know how to code, but I am learning. I've been deep-diving into everything coffee: roasting, brewing, new tools and techniques, harvesting, and geography in how it affects flavor. I've been learning Veena, which is like a really old Indian sitar-type instrument. I'm really into fashion, so I'm learning more about textiles. I've gotten into this rabbit hole about math recently. I was never a mathematician growing up, but man, math is cool. But more so about the whole concept that math is fake. Oh boy, conspiracy theories?! laughing Yes, I love conspiracy theories!

It sounds like you love doing a ton of things, and you have many things going on right now. What compels you to want to learn and try many things? It's New York City. And I know that's so corny because everyone's like, "Oh, the city of opportunity, the city never sleeps." But it's really just that. Ever since I moved to the city, something in me clicked. I met just the coolest people that do the weirdest things. Everyone here is so intelligent and so open. It feels like the world's your oyster here. I've fully embraced that personality. The city is so inspiring with its people and all its opportunities. It's been really great.

You mentioned a time before New York City—can you walk us through what that transition was like to the city or what life was like before you moved? I can start from the beginning. Before, I was living in Baltimore for four years.

I loved the city, but like man, it was difficult to live in because it's so small. It was quite drab, and it felt uninspiring. I was going through the motions there, working for two years and doing my MBA for another two years. 

But then I got a job and moved to New York City; I didn't feel anything about it. A lot of people are like, "Ooh! New York City, Yeah, I'm so excited!" But I had this conception that New York City people are really hardworking, which they are. And you're going to be in FiDi and working crazy hours, then you go home and do the whole thing where you go out, go back to sleep, and that's your day every day, and I was prepared. I was like, "Yup, I'm going to work my ass off, go to tech mixers, business meetups, and network and climb the corporate ladder."

I came [to New York], and I ended up going to a lot of tech mixers, entrepreneurial meetups, and stuff like that, but it always felt really weird and inorganic. I didn't fit in, and it felt forced. And so, I was like, "Okay, I'm gonna do that, but also try and explore other communities I'm interested in."

I knew writing was a big interest of mine, so I was like, "I gotta find a writing club in the city." I went to Book Club, the bar in East Village, where they used to have weekly or every few weeks writing sessions that were free and other workshops. In the end, people can hang out and talk. 

I had never met people like the ones I spoke to at Book Club. It's not because they're like, "Oh, I'm like the CEO of this company or whatever." It's like, this person was a full-time actor. This one person quit their cushy investment banking job to build realistic models of architectural icons around the world out of toothpicks. It's just like, "Man, you do that full-time? For real?" And it's also fun for them. 

I had this awakening that night [after the first workshop], and I remember walking home, and I was like, "The world is so big." I had no idea. I did know, but I had no idea up until now. It was crazy, and I woke up the next day; I canceled all the other mixers I was planning for.

I was like, "Why am I forcing myself to do something I'm not interested in?" And I reached out to those people I met and exchanged information, and was like, "I want to learn more about you. I love you in a non-weird way, but like tell me more. Start from the beginning, and I want to learn more about you."

That's how everything started. Then, it just really got out of control from there. I kept meeting more and more people and learning more and more about how big the world is. Now I'm like this crazy person that's just like, "Let's do everything."

Was it living in Baltimore and the contrast with your experience in New York that kicked off the way you explored the world? Before Baltimore, I lived in Rome, Italy, for some time. First, it was a study abroad program for a couple of months, and then it turned into me being employed by my college as a student liaison in Rome.

I was in Italy for a while. And you know what my personality is? Italy is my personality, I would say. laughing I'm so annoying with it, but I met this 85-year-old Italian grandma, and she changed my entire life; it's like a whole "eat, pray, love" thing, but in real life where she was like everything to me. 

We spent every day together. She's my best friend, mentor, and guide, and she showed me everything about life. If you've ever been to Italy, you know that everything feels just so romantic—like even in the movies. You can't even take a picture in Italy without it looking like it's straight out of a romance film from 1920.

That's what it feels like in person to me, too. European culture, in general, is very different from American culture. It's more community-based and laid back, and it's more surrounding the fact that you have your family and friends and spend time with them. Career jumping, career climbing, or working hard in your job—all that stuff is not as important.

What's important is taking care of yourself and others, eating good food, and drinking good wine. That's what life is about. Is it everything opposite of American culture? Yes.

It was crazy because it was my first time traveling alone without my family. It was such a formative experience, especially spending time with nonna, the grandma that I met. It was just incredible. I returned from that trip and remember being like, "I get it. This is who I want to be. Like, I don't think that life is about your career."

Unless that's what you're really passionate about, that's great. But for me, I don't, when I sit and think like, what do I want to do with my life? It's not like I want to be the CEO of this company. It's more like I want to make memories. I want to make lasting relationships. I want to try good food, and I just like helping people. So, I had that for some time, and then I think American life kind of wore down on me again.

I want to make memories. I want to make lasting relationships. I want to try good food, and I just like helping people.

And then you returned to the States after that period in Rome? I came back and lived in Michigan, where I'm from, for a year. I got an entry-level job that didn't pay much, but it was a salary, and I had never really made a salary before, so I was like, "Wow, that's cool." I was also living at home because my parents were there, so I saved a lot of money, which I'm really grateful for. And yeah, making money for the first time and having that independence.

Then I was getting into this grind of people around you telling you that you're supposed to want to climb the ladder; you're supposed to want to improve your professional skills. And I'm like, "Okay. Got it." Keep going down that path, keep moving jobs, and get higher pay and better titles. And you get into that grind, and it goes into a couple of years, and it's just like, "Okay, this is what life is."

At some point, did you go to get your MBA? So I worked for three years. And then I met my friend, Veron. I was working in Baltimore and working hard at this job. Our class of summer interns came, and one of them was this guy [Veron] who was directly reporting to our team.

He wouldn't do his work so I went to confront him and found that he was reading Letters to Shareholders. Specifically, he said, "It's really important to know how to invest and have financial literacy."

"I'll make a deal with you," he says, "I will help you invest and better understand financial literacy if you do my work for me this summer." And he's only a summer intern. I was like, "Okay, deal." 

I think meeting him and hearing him talk about this, I could immediately tell he is a savant at investing in finance. He will be humble and deny this, but he's very good. And I was like, he's got something going on. I feel like this is important. 

He was actually at Johns Hopkins doing his MBA—so he's a graduate intern. So he told me more about why he's getting an MBA and what he's doing at Johns Hopkins specifically. He's like, "I think a good move for you would be to get your MBA." And so I trust him with my life to this day. I got my MBA after that.

Do you think pursuing your MBA was because you felt you had to level up your career? Or was there some other reason behind it? That definitely was it. I wanted to first get out of the company that I was in [at the time]. I was not happy; it was not fulfilling. But see where I could be, and I was really interested. 

At the beginning of my MBA career, I was like, "Oh, maybe I'll be a consultant or go into investment banking." That died out really, really quickly, so thank God. Then I pivoted and was like, "Yes, I want to do it. I want to be in big tech. I want the name brand of working for Google or Apple or whatever it is." I just wanted that validation of, "Oh, she's smart. She knows what she's doing. She got an MBA, and then she went and worked at Google. That's crazy. Good for her."

I didn't even care about what I would do there or why I would want to do it. Again, this whole Westernized concept that it doesn't matter: just get there and do it; nothing else matters.

I felt completely brainwashed. In my first year of my MBA, I worked like a dog. I worked hard and wanted to get that four-point [GPA]. And I did all my projects and all this stuff to get that all on paper. 

Then, I started dating my now fiancé, and he was the one who helped me realize that none of this matters. And that, no offense to anyone who has an MBA, I have an MBA. It's a fake degree. It doesn't really matter. 

And he's like, "Whether or not you get a four-point [GPA], whether or not you get an A's on projects, whether or not you are the president of all these clubs will not matter, just do your MBA, you get the name at the end of your title, and then you can just do whatever you want. Just relax, have fun, and network. The people are the important part."

So, I relaxed heavily to the point of the complete opposite end of the spectrum, where I did nothing for school. I did that and then graduated with a 3.9 [GPA], which is crazy.

But it worked out really well. At the end of it, the market was starting to crash. I did an internship at a FAANG company in the middle of my MBA, as most people do. I was like, "Okay, now that I have this big tech name under me, I will get a job at Big Tech somewhere, and I can do it." It's not true. It was hard to get jobs, and I tried when I graduated in May 2022. 

It was difficult finding a new role because no one wanted to hire me. I was applying everywhere. I ended up reaching out to one person in my MBA [program] who had a connection and ended up getting my first job [post-graduation], which was the only offer I had. So I was like, "Okay, well, I guess I'm stuck with this. Like, let's just make the best of it."

Coming to the present day, where's your head now? You spoke about embracing life in a way where your career doesn't define you, but it sounded like it did pretty recently in getting your MBA and switching careers. Yeah, my career did define me. To your point, this is what society tells you; this is what the culture and tradition of your upbringing tell you. You put your sense of worth and esteem into that, which is very toxic, but it's also hard not to do that.

I'm speaking from a very high place of privilege right now to say, "Yeah, go explore the world and do whatever you want." But many people, or most people, are not in that space to do that. I got very lucky. 

If life didn't take me to New York City, if I didn't happen to be at Book Club Bar, and if I didn't meet those people and these experiences, I very well could probably statistically be on the same route. I would be a manager, director, or vice president of whatever company I don't care about. But it looks really good, and my parents are proud of me.

It was also a huge wake-up call to me that this is very much a small chance of luck, and I could not be more grateful. I can't believe I made a last-minute decision that night and decided to go to Book Club and be like, "Let me try this writing community because I'm bored of all these mixers." And [those choices] literally changed my life. My life completely pivoted from that. To anyone in this situation, I think you make your own luck. 

It's hard. I can't prescribe a one-size-fits-all, "Yes, go try everything!" But definitely don't be afraid to make your own luck and get out there; try something you've been wanting to try. You'll never know who you'll meet or what you'll experience. Don't discount anything.

I think you make your own luck. It's hard. I can't prescribe a one-size-fits-all, "Yes, go try everything!" But definitely don't be afraid to make your own luck and get out there; try something you've been wanting to try. You'll never know who you'll meet or what you'll experience. Don't discount anything.

While you're emphasizing a lot of the "well, I just happened to do something," there's a nugget in there that you're dialing down for yourself because you're very humble, Abi. Your intuition of knowing that you wanted more drove you to go and be open and try out Book Club. Because there are a lot of reasons for us to say no to things like "No, I'm tired. No, I don't want to go. etc..." Instead, you decided, "I want to try this thing and let me go and see what happens. It's a nice way to open ourselves up to more opportunities.

I often like to think that luck involves a lot of preparation and the right timing. While some things are truly systemic hurdles or boosts where life gives more opportunities to folks who are of a certain gender, ethnicity, or socio-economic status, there are moments where, outside of the system, being a little bit more open to wanting to experience things that are afforded to you, does continue to open doors or even ever so slightly. Yes! *chefs kiss*

To summarize our conversation, why does approaching our lives more openly or just trying matter to you? And why does having a non-linear "let's not climb the ladder" kind of journey matter to you? I've discovered much about what's important to me, what I value in other people, and who I want to surround myself with. In the beginning, New York City is very overwhelming in the sense that you want to do everything, like meet everyone and do everything. And I used to be such a "yes" person. I still am. Now I have a very curated group of people called Verci, and people outside of Verci that share a lot of those [similar values]. I think those kinds of people are just like multi-hyphenated people.

I want to do all the things and just share that similar mindset. You have to be careful with your time. Time is the most precious asset. I don't regret all of the time between Italy and now. But I mean, if you're reading this and you're at that point of your life, I think the best thing to do is: don't wait, like, just go out there; life is short, and it's time. Now is the time to do it.

…I think the best thing to do is: don't wait, like, just go out there; life is short, and it's time. Now is the time to do it.

Are there any other misconceptions you want to chat about? There's a huge stereotype around non-corporate climbing people or people who don't work for big-name companies, especially in the US and New York City, that you're not ambitious or intelligent. I find that false. The most intelligent people that I have met are not people who work for Google and Apple or like our investment bankers at Goldman Sachs. They are the people who make architectural buildings out of toothpicks. It's being surrounded by a community of New York City where many multi-hyphenated people do all sorts of things.

Seeing the different forms of intelligence and ambition is cool. People are just really cool. I love people. And I think it's a huge misconception that I want to stop.

People who are passionate about something are very smart about that topic or thing. You don't have to be smart about everything, but that intelligence comes with a lot of passion and determination around a topic you might genuinely love. You might be dumb when it comes to street smarts, but you might be so intelligent with the books or whatever it might be. It doesn't mean you're not a whole person, but there are parts of us. There is no one definition of intelligence. 

It's a big identity with people who are Westernized that you have to be productive all the time.

The definition of being productive is subjective, and the definition of being productive all the time is also subjective. I think that's wrong and very toxic. I used to think that if I was not doing something at all times, and if it was not productive, it was a waste of time. It was especially hard; even to this day, I'm still struggling with that.

With so much stuff going on, you can sit and do nothing or sit and have a little mini-spa day. Just walk around or have a coffee. It's okay. I recently read something where they describe time as a medium in which our life unfolds rather than a resource we always have to utilize to do things in life. When you start thinking of time as a medium instead of a resource, then your concept of "wasting time" is no longer relevant, true, or valid. Because it's exactly that, it's just like time is meant to be. It's just time. You do what you need to do at that moment. Take care of yourself. Sit and stare at a wall for an hour. No time is wasted if it's what you want to do. If it makes you happy or other people happy, just do it. 

When you start thinking of time as a medium instead of a resource, then your concept of "wasting time" is no longer relevant, true, or valid. Because it's exactly that, it's just like time is meant to be. It's just time. You do what you need to do at that moment. Take care of yourself. Sit and stare at a wall for an hour. No time is wasted if it's what you want to do. If it makes you happy or other people happy, just do it.

Similarly, Kirk Fernandes, a recent guest on west & ease, talks about treating our bodies and minds like how athletes approach performance. They need rest to do what they do. It's good to chill out for a bit and allow time to pass because time won't pass without you. The more we fight it, the harder it will be because it's a mental thing we must work towards.

I have this motto that I want to make every day of my life memorable, but that doesn't mean I have to fly out to Bali and make a trip every day. It's more like I could be sitting at home, and I smell the scent of a candle that is so yummy. And I'm like, "Wow, I love life. I love the smell of plums. Like, wow, amazing." That's also just so beautiful because it's enjoying life itself. We can enjoy both really big moments and everyday moments.

Do you have any advice for a past you that you want to share your thoughts with? Can I just say, "Stay in Italy?"  laughing  No, I don't think that's the right answer. I think what happened was meant to be happening in the time frame it was supposed to happen. I don't think staying in Italy would have been the right move because I would never have come to New York. New York City is a big formative part of my life, too. 

One piece of advice I'd give my younger self is to just "Be open." I was in a different phase of needing this advice at all points in my life. I was very competitive and focused on specific things when I was younger. In college, I was also very focused on partying and making friends, and I thought that was the thing to do. 

Even in my time in Baltimore, working and stuff, I was very narrow-minded. I had one specific goal, and I wanted to reach that goal. It's great to have goals, but I think if I could tell myself to be more open and to experience life and just take it as it is and think it's just a beautiful thing and it has so much to offer and don't shut anything else out, that would be very helpful.

I think I'd be in a very different place right now, but I love where I am right now, so it's good.

Give us a list of three things you'd recommend. You choose the topic. 

1. Tuesdays with Morrie by Mitch Albom

   1. "Formative!" is the word I would use to describe this book. He's a damn good writer, which makes sense because he was a sports broadcaster. It's a real story and memoir about him and his teacher in graduate school. His teacher found out he had some terminal illness and he was going to die. And everyone was sad, but he was just like, "No, man, let's party, rage, and make memories." The whole book follows the premise of the quote that goes like, "You learn to live when you learn to die." It's the most heartfelt, beautifully written story of this older man who just had such love for life and was ready to go. He imparted all this wisdom and positivity to his students. It's a short read, and it's so nice. I read this book before I met Nonna, but it reminds me of her, especially about living and loving life.

2. Un Sospiro by Franz Liszt

   1. I used to dabble in classical piano back in the day. This is my absolute favorite classical song from the Romantic era. When I first heard it, I cried. Well, I still cry at this song. It's a beautiful masterpiece of a composed song that I can't even describe. It felt very fitting when I first listened to it. I felt like I was going through a lot, and listening to this made me feel like, "Wow, life is worth living. This is great stuff." Like, no words to this song.

3. Nationwide Commercial with H.E.R.

   1. It's very deeply emotional for me. I really like H.E.R. as an artist, and I like it when they show montages of their day-to-day normal lives. Those two things, put together, just make me so emotional. I love people, I love life, and I love music. It's all beautiful things combined.

Favorite song or song you have on repeat at the moment?

 "I Know" by Travis Scott

I recently went to a Travis Scott concert, and it was transformative. Seriously, I cannot stop thinking about the beat and energy. And the way Travis Scott performed, he showed up and brought it like I have never seen in my life. He knew how to get the crowd going.

Enjoyed the Conversation with Abi Suresh? Learn more about Olive Tree Writing Club, which Abi co-hosts @otwc_nyc on Instagram. You can also follow her writing at www.verbinding.org

Verbinding

Verbinding; a collection of short stories about real, chance encounters with strangers. It’s a window into the feelings of sonder and longing for connection.

By Abi Suresh

Abi is also passionate about giving back to The Bowery Mission.  

The Bowery Mission exists to promote the flourishing of New Yorkers overcoming homelessness and marginalization by providing compassionate services and a transformative community. A donation was made to The Bowery Project as part of this Conversation.

You can support The Bowery Project by donating directly.

Donate to The Bowery Mission

Meet Sam Ray Lee, a musician, singer, songwriter, UI/UX designer, freelance photographer, and one-half of the musical duo Umami House based in Brooklyn, NY. Sam's creative journey starts from an early age. It morphs into an integral part of his identity, with each new pursuit growing and adapting to particular periods of his life. He shares how music came into his life and temporarily left when he married at an early age and how divorce brought him back to embracing and pursuing his creative musical journey. That and how other creative pursuits like photography and design have enabled his musical journey. We also get a glimpse into the origin of how Umami House came to fruition and parting advice for his early self as he set off into his creative journey and identities. 

Interviewed in December 2023

Heads up, the interview contains some explicit language that may not be suitable for all audiences. This conversation has been edited for clarity and brevity.

Can you introduce yourself and what you want the audience to know about you? Hi, I'm Sam. I'm newly based in Brooklyn, New York. I am a musician, singer, songwriter, UI/UX designer, and freelance photographer. Also, on my naturalization certificate, since I became a citizen in the summer of 2020, it says divorced. 

Let's take a step back: could you pick a point in time to share the origin of how your creative pursuits started since you mentioned so many different parts of your identity? I find myself at a crossroads between many creative avenues and mediums right now—music, photography, design, or creating content. Whatever I do in my life that I love has something to do with creating something. 

And so, the day that started for me was when I was 12 years old; my mom got me a "birthday gift": a guitar. She just wanted me to start extracurricular activities, but that was the first time I got totally obsessed with something. I remember I broke my right arm within the first month of having that guitar. I wore this giant cast so that the first guitar had all these marks from my cast. That's how obsessed I was with playing guitar.

I was always the person who, while I had friends, also had a loner personality. I would skip lunches sometimes in high school and just go to the guitar ensemble room, pick up a guitar, and be that strange kid just playing in the hallway. That was when I found playing guitar was the place where I could retreat from my life.

In your present day, you're spending a lot of time creating. However, looking back at the moment you picked up your guitar, was that the first time you were learning to create or just experiencing it? Are you just jamming to play music versus playing the guitar to have a tangible outcome? I was just experiencing it for sure. I didn't know what I was walking into, and I just knew I had enough of a knack for it. And it was something that I could continue learning and almost build a relationship with that guitar. That led to this wonderful thing that keeps happening even today, where the music I played or connected with connected me to other people and friends I would make later in life.

[Playing music] led to this wonderful thing that keeps happening even today, where the music I played or connected with connected me to other people and friends I would make later in life.

When I first started playing, my mom signed me up for summer camp at church, where I found these worship leaders playing guitar. They brought me up to be a worship leader. And that exposed me to all sorts of relationships that I would build with music. In that church scene, you're not only playing music but also worshiping, whatever your faith might be. That was kind of a reflection of my life where music was something more than just noises that you made with an instrument or notes you're singing. It was something that connected me to something way bigger than life. 

Even today, if I'm playing a show or writing a song, I sometimes think back to those moments when I would "worship" and reach certain highs in music that you're not always able to reach or find in your regular life. Music always felt like something bigger than just myself.

Is creation also a form of communication? Or is it more connection with communities or whatever is around you? I would say it's a form of communication for sure. Because there are people I've met, before even saying any words to each other, we would have a musical conversation. I might play a few notes on the guitar, and they're able to swing something back with whatever they're playing or singing. And that's happened with many relationships. Fast forwarding to now, these are some of the best buds I have in my life. And that didn't mean those relationships didn't start because I went up to them and said, "Hi." It was literally just this instant connection where we were both having a moment. And having conversations with one another just via music? Yes. It's probably the closest thing you can get to, like love at first sight. Or love at first "hear"? Laughing

That's very different for me because I don't create any music but am a huge music consumer. That feels a bit more one-way than what you're experiencing: a full two- or multi-way conversation via music. I find that a lot of people have a favorite artist. I assume one of the reasons they love that artist is because they feel understood by that artist. That artist is creating songs that make the consumer feel understood. That's the same sort of feeling that you get when you're jamming or just in that creative space. 

I could be playing something. I look over, and a guy's looking at me, and he just nods his head or has a stank face on. And I'm just like, I feel understood. No matter what degree you feel understood by someone, this instant connection exists. 

Were there other creative pursuits that started around this time? Throughout all of middle and high school, I thought it was going to be just guitar, a bit of singing, and then also some writing. But guitar was certainly my main voice, the main boat I would take on my creative journey, and I didn't think I would do anything else. It was like when you were still living with your parents at that time, and your world was only as big as you know. You have less freedom to venture out.

After I graduated high school, my mom moved out to L.A. I moved in with my best friend's family because I wanted to live on my own, get my own room, and figure that out. So, I was still in Fairfax, Virginia.

At that time, I could not for the life of me figure out the transition period from graduating high school and what college to go to next. I didn't really apply to many colleges and eventually caved and decided to go to community college until I figured out what I was going to do. So, I went and studied music.

I figured it was like, "Well, what else would I do?" The logic for me was just, "Well, I'm going to do this music thing anyway." So, when I got to the community college, I ended up hating my professor. It was probably the format of learning for me that just wasn't very helpful.

At a certain point, I realized I didn't need [school] to do what I love with music. So I dropped out, and that was the first time I dropped out, and then I didn't know what I was going to do anymore. My best friend at the time was doing a lot of freelance videography, so I picked up a camera. I was like, "I'll try out some videography," but then I ended up just falling in love with still photography instead. And I instantly got obsessed with that and started buying lenses and figuring out what I liked.

Were you learning photography and videography on your own? Yeah, I figured out which photographers inspired me, like Trey Ratcliff. It was the first time I ever cared about anyone's photography style. He was a pioneer in HDF photography, which is when you take multiple exposures of a single image where it's underexposed, regular, and then overexposed. Then, you combine it all together, and what it does is give you this highly detailed, wide dynamic range. The highly detailed photo shows you everything in the shadows and highlights, and it provides this capability for a really overly colorful image—like stuff I would never edit today. But, at the time, I thought it was really cool. 

Then, I realized there was this whole world in both composition and post-processing. That was really cool because I figured out that when you take a photo and edit it, you express your reflection of that moment and what your perspective is. And so, that was a parallel to what I found in music where I was like, "Wow, this is how I self-express in photography." Especially in the process of editing in photography? Yeah, especially when you're editing. Composition matters because that's your style of how you're choosing to capture that moment. But there's this whole other world that's unlocked when it comes to editing.

What about design? How did you get into pursuing design? So, I did freelance photography for a while and would get these gigs on and off. It was one of the most fun phases of my life, and it enabled me to travel and just fuck around and have fun. laughing 

But then, it wasn't consistent income, so I was trying to figure out how to make it. Design was that solution because I talked to my cousin at one point, and he was a Graphic Designer at Lexus. And he was like, "If you're looking for something creative and trying to make money, why not try design?"

I went back to community college and started studying some design courses. I wasn't very good. I remember we had to make a vector sandwich on the first day of class. It was just about teaching you how to trace and create shapes and stuff. I remember thinking that my sandwich looked so bad compared to everyone else. So I was very behind and had to quickly figure out, "Okay, how am I going to survive this?"

Through photography, I had a really good eye for composition and figuring out visual hierarchies and how to balance certain elements. I also had a knack for typography and how to utilize it. As I said, I was a really terrible student, so I ended up learning design on my own outside of class.

I would skip some classes and show up to the presentation phase. And then, in the middle of that, I got an internship at a digital marketing agency, which eventually turned into a full-time job offer. 

I dropped out of school again because school was teaching me about print—which I loved the idea of more than executing. And so, I was like, "Well, I can just learn through this job." And that's what I did. It was an awesome experience because, through design, I had to learn a lot about what collaboration looks like and work with so many different roles, departments, deadlines, etc. That was probably the first time I fell in love with design because of the collaborative aspect of it. 

Were you collaborating through music and photography at that time? Not really. Music was the church band, which, of course, I had to collaborate on. But, I think for me, [music] was special because it was self-expression, and it was about letting something out from within me. Then, design was all about the client. I never actually experienced design in a way where it was just me creating something to just create something.

Do you think there's a difference between how music, photography, and design allowed you to collaborate and self-express due to how they came into your life? With guitar, it was more "try this" versus photography, and design came about as a way to survive. Is that still true today? For design, it is, in a way, a means to a living. One thing I like about design is that you can find a lot of design roles out there. There are so many places that need designers, and I guess that's where the true feeling of safety comes for me—in terms of making a living.

The reason I'm at my particular [role] now is because it also feels really good to do something that's actually making a difference in the world. A lot of our clients and the spaces that they're in are very focused on progressive movements, including social justice. And so, it feels really good to know that you're doing something positive. 

I asked this question because, as a designer, I speak candidly with many people about this topic. Product design is my day job, and I appreciate everything it's provided me. It's also something I've wanted since I learned about what it was, considering that it could bring me further in my career and life. But, at the end of the day, I don't think that's who I am or will be forever. 

It feels like a cop-out because I don't know what else to do or who I am, so I'm so attached to this role and identity. So, I always love asking other people, especially designers, like, "How did you know you wanted to be this forever?" Because I didn't, and I didn't even know the role until I stumbled into it. That survival mode kicked in for me as a kid with immigrant parents, and the amount of money one could make as a product designer was a big draw for me to do that rather than graphic design. Does any of that resonate with you? Absolutely. I completely forgot [to share] about this one chunk of my life where, between photography and design, I got married really young. 

I got married at 21 and divorced at 22. That was the period in my life when I realized that I already had been designing. But by the time I got married, I realized that design suddenly took on a very different role in my life.

And with design, I can see a path where I can figure out how to make even more of a living through design so it can support a potential family in the future. Design definitely had a very specific and heavier role in my life at a certain point. Heavier because it could afford you a certain life? Yeah, because it was the one thing making me real money. 

And so, I was like, "I gotta be really good at this now" because it's not just me alone anymore. Suddenly, it's me with my wife and our pets. I felt a lot of pressure then to perform really, really well and take myself more seriously, especially on the business side. That includes how I talked to managers and directors and learned how to put on a different face. A bit of code-switching? Yeah, because most of my life, I've been flying by the seat of my pants. And that was a moment where I was like, I can't do that anymore. I gotta follow through with this and this imaginary syllabus that I had in my head for how to be very successful at design. 

I don't feel that pressure anymore. I don't even know if I'm going to do design for the rest of my life at this point. 

So what happened next—what was the switch from where you were to where you are today? The switch happened once I got divorced. It took me really working on myself all the way up to the point where I was just like, "Okay, it's not just me; I'm living a very different life now where I'm trying to support other people in my life." 

And then all of that, just like poof—disappearing really, really suddenly. It was really weird for me. I'd been in this relationship for four years, and now it's just me by myself. I had an identity crisis because I was like, "Well, what do I like to do in my free time?"

I was stressed out when I was married because of those pressures, which taught me a lot. But, at the end of the day, it just wasn't good for me mentally. So when that mental space was cleared up, and I had to just focus on myself, it brought me back to certain things like music because when I was married, I didn't play much music. I had to come back full circle to music.

Walk us through that experience and how Umami House started. I was still in Fairfax when I divorced in 2019, right before Covid [the pandemic]. It was 2019 when I got back into music and realized I loved music. 

Around that time, I thought I was going to quit music. I was selling all my pedals and posted on social media [about it]. I can't imagine you doing this! I was getting rid of a bunch of guitars, and [our friend] Alfred replied to one of the stories that he was interested.

How did you meet initially meet Alfred? We were friends already because we met back in 2016 at an open mic. Alfred was still in college then and then moved to New York. We didn't hang out for a long time, and I was still single before my marriage when I first met Alfred. And then, after we first met, I went through my whole married life. Alfred went through his life in New York, and we had very separate paths. 

So when he replies to the story where I'm selling my pedals, he's like, "I'd love to check out what pedals you have." He came over, and while he didn't buy any, we jammed anyway. And I realized, at that moment, like damn, I still really freaking love playing and realized, shoot, I just sold some of my favorite pedals.

But it was great because I got to explore a totally different side of music. I had sold a lot of my gear and was stripped down to just one guitar, which was a Taylor GS Mini. It's not even full-size, and I don't think I even had a single electric guitar at the time. Real back to basics.

And that was when I started really exploring songwriting again because suddenly, it wasn't just about ripping it on the electric guitar. Which we know you can do! laughing Yeah! You know, like, all the distractions were gone. I had an acoustic guitar, my computer with Garage Band, and a lot more time with myself. And there was certainly a lot to write about, so that started a new era with music for me.

I approached it very differently. At that point, the guitar and I were going for round two, like in a relationship with someone, you know? You approach it very differently.

Were you more open to embracing your music to try something new? Or did you feel you had the same approach when you first picked up the guitar? I had a very different approach. I almost stopped caring about learning at that point. 

For me, musically, I cared a lot about learning. Whenever I play a show with this really good guy, I think about how I can't play as well as him and all this stuff. But at a certain point when I was in that phase, around 2019 and 2020, I realized I had all the pieces that I needed. I have a lot more to write about now. And so, let's see what we can do with it. And I never thought about it that way before. Once I acknowledged that, the ball started moving.

So, how did you and Alfred start Umami House? So we reconnected, and Alfred returned to the Northern Virginia area during Covid. Then, we started hanging out a lot. Eventually, I introduced Alfred to a lot of my friends, and then a lot of Alfred's friends and my friends started mixing. It was just very natural and more than just jamming together; natural friendships started happening.

Like, there was one day when no plans were made, and no one could have predicted this. It was a random Sunday afternoon, and Alfred asked me, "You want to go to New Orleans?" He wasn't thinking about New Orleans at that point, and I think we were just on a phone call, and I was like, "Man, that one time in New Orleans..." And then Alfred was like, "You wanna go?" I was like, "Yeah, why not?" We were both working remotely and went on this two-three week-long trip. From New Orleans, we headed to Colorado, Utah, and Vegas somewhere. Really freaking random.

Suddenly, this friendship had developed to the point where it was like, "Oh, here's another guy who knows how to roll with the punches and be spontaneous." Because, my whole life, I've been very "flying by the edge of my seat," and it was cool to find someone else who had that similar energy.

All the while, we're still jamming together occasionally. When fall eventually started, we became roommates. And by winter of 2022, we're in Montana at this bar in the middle of nowhere, and we're just talking about how we've been friends for this long, and we all play this music together. We throw a lot of parties, and at the end of the parties, we forget that we're hosting and play a lot of music. 

And so, we were like, "We're not gonna leave this bar until we come up with a name for this new band," That's how Umami House came to be. Then, from there, it was just figuring out, "What does this mean to us? Where do we want to go?" And we've been a duo ever since.

Why is any of this important to you overall? It's important to me because when I'm having day-to-day conversations with people, you're not always entering the deep zone with every single person...because that'd be weird or pretty intense. But whether it's music or creating some sort of story for design or photography, you're expressing yourself in a way that you can't always express with words to other people. 

For me, it's always been like a retreat. Or just this way to connect myself by creating that art. Otherwise, I don't know where I would put all that energy.

Is it a way to connect with yourself to then be able to connect with others? I will say it has always started with just being for myself and connecting with other people; things just happen naturally. Because you get to know yourself more through that process of creating. For example, let's say you're painting something, and you paint for hours and hours and hours. You take 10 steps back and look at that painting, and you're like, "Where the hell did that come from?"

And with songwriting, I'm trying to practice a lot of honesty when I write songs. There's this line that I heard once where someone said, "You know, if you feel like you're oversharing in a song, then that probably means that's good because that probably means that someone else out there will get it." That really stuck with me.

These connections with other people through music just naturally happen because I am trying to be honest with myself, almost overly honest. And when that side shows through whatever I'm creating, someone else out there really does get it because it's true and genuine. Because of most things you go through in life, there's a good chance that someone else has felt or experienced those things, too. But you never really talk about it. So, if you're expressing that through the art, someone else out there will hit their radar.

Because of most things you go through in life, there's a good chance that someone else has felt or experienced those things, too. But you never really talk about it. So, if you're expressing that through the art, someone else out there will hit their radar.

Let's talk assumptions. One assumption people may have of you, myself included initially, was that you're a full-time musician. Living in D.C., you get the "What do you do?" question almost all the time. More than New York? Way more than here. It depends on the crowd. Because I think there's this shared understanding across a lot of people [in New York] where we hate that question. You're self-aware about it. In D.C., that's all that other people cared about. So whenever people used to ask me, I used to answer, "UX designer." I didn't realize that I was doing it because of this, and that automatically gave me a card into a certain social circle or amount of intrigue.

And so, I used to do that and realized a lot of people back then didn't realize I did music at all. I just had this switch turn on in my brain where I was totally embarrassed by the fact that I create music and afraid they'd judge me for it. That's so different now. 

I made this conscious decision to be like, whenever people ask me that next, I'm going to say musician because that's what I want to be. That's what I want to be doing more of, and if I don't take myself seriously, then why would anyone else take me seriously? Even my Instagram has nothing but music on it.

I made this conscious decision to be like, whenever people ask me that next, I'm going to say musician because that's what I want to be. That's what I want to be doing more of, and if I don't take myself seriously, then why would anyone else take me seriously?

Fast forward, it's all flipped for me now. Now, a lot of people don't think that I do any design work, and they just know me as a singer or musician. A lot of people don't know that I work eight hours a day or more doing design work while trying to juggle everything else as well.

How do you balance it all? One of the misconceptions for those of us who have full-time roles and do something on the side is that it's continuous. For west & ease, people often ask, "How do you prioritize all of this?"

My usual answer is, I don't. I have no time, but I'll have spurts. For example, my last interview was in May 2023, and I only recently posted it in October. I didn't have any capacity to focus on it, and I'm finally getting my second wind for the year to try again. But many people don't know that they think it's continuous. 

So, do you feel a similar pressure or misconception around balancing and juggling all these parts of your identity? I feel some pressure, but I don't think it comes from other people.

It's anything but that for me. What you think is really obvious to you is not actually that obvious to most people out there. That definitely shows through design and marketing.

Part of the reason why people think that I am a full-time musician is probably because some of the branding I do around my social media is very intentional. It's still real stuff, but I'm being intentional about what I'm sharing. So I've never felt the pressure from other people. 

And how do you balance it? I...sometimes don't. laughing Sometimes there's like nothing I can do. There are phases where I'm doing a lot more. Most of the time, I'm doing a lot more design work than music.

But, this move to New York has been quite the transition. I had this problem in D.C., too, but like saying "no" to going out—I'm still really bad at that. I'm realizing these days that I just need to have time for myself. And I need a bit of quiet time because if you stop shaking the bowl, everything will just settle, and you get to figure out, okay, where is everything in my life again? So, taking more time for myself to create.

Switching gears—what advice do you have for your past self who started doing what you're doing now? "I know it doesn't make sense right now, but I promise it will one day." laughing I felt a lot of pressure when I was moving from music to photography to design. I went through, as creatives do, at least once a year, I went through so many identity crises. Like, "What the heck am I doing?" 

I know it doesn't make sense right now, but I promise it will one day.

There was a lot of worry about never being able to do what I love ever again. Or just worrying a lot about, like, "Who am I going to be like ten years from now?" And I would never have expected any of what's going on today, five or ten years ago. I would tell myself that it'll all make sense and just keep doing what you're doing because things come back full circle. Eventually, you'll learn what you learned during those times, and then, later on, it will come back to you. You'll look at it in the face again and be like, "Wow, this is just right."

I would tell myself that it'll all make sense and just keep doing what you're doing because things come back full circle. Eventually, you'll learn what you learned during those times, and then, later on, it will come back to you. You'll look at it in the face again and be like, “Wow, this is just right.”

And still, even now, there's so much I don't know what the heck I'm doing sometimes. But it's nice to look back, and you're just like, "Damn, these pieces really did come together." They are still coming together, but it's cool to see the progress.

Give us a list of the top 3 things you'd recommend.

My 3 tips for starting to learn photography!

1. Get yourself a prime lens! It can be really easy to get distracted by all the bells and whistles of your gear - so sticking to one focal length can really help you figure out your style as you're forced to move around and 'hunt' for the right shot. My first prime was a nifty fifty (50mm prime) and it was instrumental in helping me figure out my approach and which gear I really need next.

2. Don't be afraid of post-production/color grading - in fact, go crazy! 50% of the art is shooting and composition, and the other 50% is how you choose to edit your work to best portray how you experienced the moment. Every photographer has their own perspective on life and it's up to you on how you want to reflect that perspective.

3. Trust your opinion. There'll be a lot of people giving you advice along the way - some of the advice will probably be really helpful, but trust your gut and recognize that your opinion on the matter, matters. For example, if you want to shoot super blurry images and you feel something special out of it, why the hell not. If you want to make your photos super saturated because that gets you excited, lean in. Figure out more of where that excitement is coming from.

Favorite song or song you have on repeat at the moment?

"Call Your Mom" by Noah Kahan ft Lizzy McAlphine

Going back to what I was saying before about being honest in your songwriting, it's not just about being honest but also about being vulnerable and reaching for a vulnerable audience through songwriting.

This song does such a good job of that; it's talking about a moment where you're talking to a friend who may not be in the best mental state. They're probably really depressed in whatever situation they are in. The lyrics are examples of what you'd say to that friend.

It really hits you deep because it's certain lines that take you back to certain moments in your life where you're like, damn, I remember the times when I've had to say that to someone.

Enjoyed the Conversation with Sam Ray Lee? You can follow him at @samraylee and @umamihousemusic on Instagram. You can also listen to Sam and Umami House’s music on Spotify.

Sam is also passionate about giving back to Send Chinatown Love. 

Send Chinatown Love's mission is to respond to the needs of Asian-owned businesses by providing customized services and resources while also creating opportunities for our community to connect with these businesses. With all initiatives, Send Chinatown Love hopes to build a more resilient future for these businesses and NYC's Chinatowns. A donation was made to Send Chinatown Love as part of this Conversation. 

You can support Send Chinatown Love by donating directly.

Donate to Send Chinatown Love

So you might hear some mentions of Patreon, but switch that out with “Subscribe on Substack” and you’ll get the idea.

Interviewed in 2020. This conversation has been edited for clarity and brevity.

Welcome to a west & ease subscriber exclusive. west & ease is a collection of stories, sounds, knowledge, visuals, and "creative" work. Specifically, you're listening to an exclusive clip from a recent Conversation with Kevin Twohy. You can find our original conversation here.

Meet Kevin Twohy, an independent product designer helping early-stage startups go from zero to one. He shares with us how he got started in his career, how he's steered himself into the creative, independent world, and gives us insight on how to approach it ourselves.

For this exclusive, we'll hear directly from Kevin about a recent project he did with Hellosaurus. Hellosaurus is a new interactive video platform for kids to watch and play along with their favorite shows, truly reimagining screen time for a touch screen generation. Kevin shares with us how the idea came to fruition and walks us through the process from start to launch.

Bonus links: Kevin shared with us a few links during the chat, including:

• Kevin's tweet thread about Hellosaurus with visuals

• Nielsen Norman Group research on how to design for kids

• A book on how to Design for Kids

To learn more about Kevin and his work, check out his website at kevintwohy.com and follow him on Twitter @kevintwohy.

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Music by mariokhol from Pixabay

Welcome to a west & ease subscriber exclusive. west & ease is a collection of stories, sounds, knowledge, visuals, and "creative" work. Specifically, you're listening to an exclusive clip from a recent Conversation with Jay Demetillo. You can find our original conversation here.

Meet Jay Demetillo, a Filipino-American designer whose career and life spans worldwide. He grew up in New York, making his first cross-country move to design in the early days of Silicon Valley. He eventually made cross-world moves to further experience and embrace living an international life while navigating his design career. Over time, his experience helped him expand his worldview while actively contributing to East and Southeast Asian communities.

For this exclusive, we'll hear directly from Jay about his recent projects with Grab, a Singaporean-based tech company providing ride-hailing, deliveries, and financial services in Southeast Asia. Jay shares insights on how privacy and safety are crucial to ride-hailing services like Grab and themes and learnings from two projects: Audio Protect, which introduced audio recordings during rides, and Telematics, which focused on enabling and encouraging safe driving habits.

Bonus links:

Jay shared with us a few links during the chat, including:

• Grab Audio Protect: https://soyacincau.com/2023/03/09/grab-rolls-out-audio-protect-to-help-solve-safety-related-ehailing-disputes/ 

• Grab Telematics: https://engineering.grab.com/telematics-at-grab 

You can learn more about Jay at:

• Embracing an international perspective through design with Jay Demetillo:

  https://www.westandease.com/p/conversations-with-jay-demetillo

• Learn more about Jay on Linkedin and Instagram @asianxjay.

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Music by ComaStudio from Pixabay

Recently, Tiffany Trieu and I were invited back to our alma mater, UC Davis, to speak with students in Design 001: Intro to Design course led by Professor James (Jim) Housefield and Professor Katia Canepa Vega as part of the broader "Voi…

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Meet Kirk Fernandes, Founder of Merit—where tech workers find mentors, get career advice, and connect with the best companies to grow their careers for free. Kirk shares his journey and inspiration for starting Merit and how he incorporates his whole self into his role as a founder. We deep dive into Kirk’s interpretation of work-life balance, which he defines as spanning over a long period of time through investments in relationships and rejuvenation. He also offers a simple framework of how he keeps himself and others close to him accountable for the overall health of his company, physical self, and relationships with others. Ultimately, he offers not advice but his own experience to inspire you to make informed decisions for yourself, whether or not you're a founder.

Interviewed in June 2023

Heads up, the interview contains some explicit language that may not be suitable for all audiences. This conversation has been edited for clarity and brevity.

Tell us about you and what you'd like the audience to know. I'm Kirk. I'm the Founder of Merit, a mentorship to sponsorship platform for the under-networked tech worker. I'm a Canadian who spent his life working in America in big tech like Microsoft and startups like Hightower and VTS. 

The thing I'm most passionate about building is great products and great teams. And now, at Merit, I'm focused on building great brands and understanding the marketing side. Merit is a thesis on my view of a tech career. Merit's been the final stage, or the Ph.D. of my career, if you think of it that way. 

Let's rewind a bit—what led you to want to pursue creating Merit? I went to the University of Waterloo, which has a co-op program. They have all these relationships with companies, and you do internships every three or four months. That program in Waterloo got me my first job at Microsoft. Microsoft set me up to come to New York and work at Hightower. Hightower got me into VTS, and many people I worked with in VTS became early users and investors in Merit. So, I had this initial kernel of a network bootstrapped by Waterloo. And I realized that my whole career can be traced back to all these people, and this network keeps expanding. 

To me, Merit would be this mentorship platform that essentially hacks a network for the tech worker. Going deeper into the industry, I've learned that the vast majority of people entering tech are under-networked. They don't live in a major tech hub in this remote world. A lot of them are coming from boot camps and state colleges. They're not coming from [University of] Waterloo, and a huge chunk of them are from an underrepresented group, like being a woman or person of color. The vast majority of tech actually experiences this problem. So, Merit is the solution to the hypothesis that networks grow careers, but most people are under-networked.

While Merit is at its current state, it's not the end state. Were there any particular moments leading up to Merit where you found the flip side of not having a network was like? Yes, when I was managing a team at VTS, it was a big product management team with six very diverse people—ethnically, gender, and background-wise. Often, they would have very particular questions like "How do I negotiate this raise?" and I would give my advice from my perspective as a man, but I'm also like, "You should talk to women. There are nuances of how you ask for raises as a woman." So I would be like, "There's someone I know who is more senior; you should talk to them." 

And then I realized if I wasn't there to facilitate that connection, like, what would happen? Are we just going to depend on a random chance network of your manager if your manager is willing to do it? I saw how much I was not just the enabler but also the blocker of some of my team's growth. So I was like, "Why leave it up to chance and the manager?"

When I started Merit, it was actually like, I wish I could have given this tool to me as a manager because a lot of times, my reports had questions that I didn't have the answers to or network to get to. Even my own network came up kind of limited. From the very personal point of view where I was managing under-networked people, it was a very limiting function. Merit is similar to my network but at scale. Why depend on just me? Why not depend on 8,000+ people?

Were there any moments you found you needed somebody, like a mentor, as you navigated your role as a manager to now actively building Merit? Every day. I use Merit to build Merit. It's about making it more socially acceptable for people to ask for help. That's the hard problem on the mentee side. So practically, not only are Randy [Brown] (Merit founder) and our team mentors on the platform, but they are also mentees. When we have an issue, we go through the index and find people to talk to.

We use the platform every day, and I would say people don't use it enough. But, the more senior you get, it's a little bit harder to ask for help because the questions become so specific, and fewer people can theoretically help you. But there are always people that can help you.

So, for me, I've been using Merit to build Merit. And, the way we've capitalized our company, we have a community of investors. We have tons of people that we tap into every month to ask for help. It takes a village to build a company, and we literally have a village of people. 

As a founder, what are some of the hardest things you've had to ask for help? You mentioned that it's tough, especially as you get more senior. I think of being a founder as almost niché. Investors are very specific because you can ask for intros for feedback and give advice on very tactical things. 

The really hard problems and scary stuff as a founder is when things aren't working, and you don't know what to do since you've never done it before. Some investors usually have been founders before, like Gary Chou or Donald DeSantis, who we talk to. They understand, and there's a level of empathy. 

Ultimately, I have a peer group of founders who are just friends. And we hang out more casually or in the group chat. And that's something where you can be a little more honest about how chaotic, scary, weird, and how made up all of it is. Because you can't really be that honest to your team and investors because you want to project a level of confidence to show that you know what you're doing. But sometimes, you don't know what you're doing and make it up as you go along. You just have to be right, eventually.

I always tell other founders that I learn the most by talking to other founders at my stage or the stage ahead in terms of actually debugging your company and being better as a founder. An investor has a very specific relationship where you're trying to make them money, and employees work for you. You're in between them and their paycheck. So you're not always going to get that level of honesty versus someone who is just a founder who would let you know when something you should do or not do more honestly. The founder peer group is where I found the most learning, and I've just been lucky to have a lot of founders in my orbit. 

What is the day-to-day like as a founder? Day-to-day, it's very different. For example, today, I have an interview with you, a team retro, two pitches, and a coffee catch-up. It's going to be a ton of emails. Today's not a super interesting day. laughing 

But some days, it's like planning an event, or it's going deep on the product. Some days, it's focus on teammates who might not be doing so well and need to do active coaching. So it really depends. 

But the high-level job of the founder is to essentially define a mission with a high-level goal and metrics.

And, essentially, don't run out of money. So, like selling to investors and customers and then hiring and managing the team. Those are three of the responsibilities that'll always be true. 

I kind of view it a little bit more like the metaphor of a firefighter. When there's not a fire, you're in the firehouse cleaning, making things better, and working on the next version of the company. But, when there's a fire, you have to go put out the fire. Right now, my number one thing is fundraising. So, until fundraising is done, I can't go back and work on the next version of the company. The metaphor [of being a firefighter] is a little bit better than another metaphor that some people talk about the CEO as a salesperson. 

Right, I hope you're currently in the firehouse, and that's why you're having this conversation with me with no fires burning outside! Yes! Maybe right now, it's like a low simmer. But today, there are no fires right now. 

Also, being a founder is so subjective. It depends on the company, the stage, and your personality. And we have co-founders. Like Randy, my co-founder has responsibilities that are more on research and development to keep building the product. My responsibility is more on marketing and money, including understanding sales and capitalization. So you divide and conquer—it's rarely just one person. It's a very unique situation, and it's what you make of it. The key responsibilities are true from start to end game—it just changes. 

Could you share some of the highs of being a founder and maybe some of the lows? The highs are like, "Oh, this is working!" It's when it's obviously working, and people are getting a lot of value out of the platform. Or, we closed the sale we got from four customers to 10. Or that we recently crossed over 7,000+ users. Or that we have really cool designs, and we're going to ship it. And there's a new teammate that just joined, and they're doing a great job. Or unsolicited feedback that goes viral on Linkedin. So those are the high highs. 

The lows are just as numerous. It could be that the website goes down or someone has a really bad experience on the platform. The lows could be you pitch 10 people, and they all say no. The lows could be that a teammate's not working out. A low could be you just forgot to do something. The lows could be that a competitor launches something slightly better than what you were building, and you have to rejigger your plans, right? The lows can be numerous. 

What I've learned is that as you go deeper, you can't make the lows any lower. You actually care more the deeper you go into it. So all you can do is make the highs higher. laughing Like you can't avoid disappointment. It's like a roller coaster—you can't be upset when it goes up because it'll also go down, right? It's the same concept, so you must embrace that. [Being a founder] is not a steady journey.

What I've learned is that as you go deeper, you can't make the lows any lower. You actually care more the deeper you go into it. So all you can do is make the highs higher.

One of my assumptions about being a founder and hearing from peers embarking on the founder's journey is that there's a lot of work. Is that true or is that a misconception? It's a lot of work, no matter which way you cut it. I actually have a take that whether you bootstrap it, angel invest it, or VC back it—it's the same amount of work to start from zero to one. The time you spend is like just building a small business is just as hard as building a big business. This is why I always tell people that you might as well build a big business. 

It's a lot of work. It's a lot of hours. The best metaphor is like an athlete. You have to train and perform. There's just a raw amount of hours, and you can't cheat that process. But you shouldn't make it an excuse not to care for yourself. That's the line. You have to sleep, and you have to eat, I assume. laughing Yes, you have to! 

The best metaphor is like an athlete. You have to train and perform. There's just a raw amount of hours, and you can't cheat that process. But you shouldn't make it an excuse not to care for yourself. That's the line.

You have to take care of yourself mentally. And you have to invest in some level of relationships or rejuvenation—whatever that is for you. So, I think you have to treat yourself like an athlete, which is like, take yourself seriously, don't sacrifice or punish yourself. Being a founder is not martyrdom. Like, no one told you to start a company! laughing Even for those who did get told to start a company, this is still great advice! I genuinely mean that! You chose to be a founder, so don't punish yourself for it. Enjoy it. 

It's a lot of work for the founders and the team. The team works a lot, too. So, at the start, even good companies, they pushed until the very end. Some companies like Apple are still cranking even though they are a 40+ year-old company. It's a sacrifice and hard work, but you have to treat yourself like an athlete and understand what performance is like. It's all about increasing the company's performance and not just slaving away and stuff.  

Was there any series of instances or a pivotal moment for you in your founder journey where you realized this insight? When I was fundraising, I got Covid and had to take two days off. And I came back the next week, and all my pitches were 20% better. It was because I slept for two days. I was like, "I'm a fucking idiot!" Like, I should have just slept. You just have to be self-aware, and sometimes, what you need to do better is to take time away. 

Suzan's Fieldnotes

Leading a Startup While Navigating Personal Strife

Being a leader, especially one of a startup can be more than a full time job. What happens when stressful things happen in your personal life? I talked with Kirk Fernandes, Co-Founder of Merit about how he handled this when three members of his family got sick. Our conversation covered why he started Merit, what he learned about asking for help, the imp…

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4 years ago · 4 likes · Suzan Bond

Totally, and this brings us to the theme or term "work-life balance." I'd love your thoughts on that—especially how you apply that to what you do? I think work-life balance is kind of a weird term or misappropriated. Ultimately, you want to feel like your time was well spent. That's what you want to do. You want to maximize no regret. 

So, I do think you want balance, but over a 20-30 year period. There will be certain periods where you'll work more and certain periods where you work less. For example, my family was sick, or my wife needed my help, and being there for them was the most important thing, and work had to suffer. Something had to suffer. There are all these tradeoffs, and you can't have everything all at once. But over a long enough period of time, you can as long as you're strategic around it. 

I do think it's a little bit different as a founder or business owner versus an employee. The leverage you have as an employee is that you can quit; there are always jobs. Right now, there may be a tightness in the job market, but in general, you can leave, and that's your superpower. [As an employee], you're not tied to a company. As a founder, it's a bit different. You can quit and shut down the company or leave—but your superpower is that you don't. So you kind of change the reality around you to fit your lifestyle. 

Founders integrate more of their lives into their work. You can see it in companies where many founder personalities end up becoming the company's culture. Whereas, as an employee, boundaries and structure are good for carving out your life. Ultimately, it's just about time spent and how you want to spend your time. 

That does come down to meaningful time spent with other people. So, this is a hyper-subjective question. The big thing I don't like is when people project their own value system on others because everyone has different value systems. So it's not my place to tell you what to value, but I can give you advice on how to get there. 

Do you have an example of how you're applying this to your life? How are you integrating your life into Merit as a founder and as Kirk, the human? So, I spent a lot more time going to events and meeting people in the community because I get energy off of that. I'm slightly more extroverted, so I integrate more of that. I take that workload from other people in the company. For me, it's less about integration and more about energy and rejuvenation. So if I'm doing stuff that's draining me, I try to design a world where, the next day, I have something that's rejuvenating me, so then the day after, I have more energy. 

For me, it's less about integration and more about energy and rejuvenation. So if I'm doing stuff that's draining me, I try to design a world where, the next day, I have something that's rejuvenating me, so then the day after, I have more energy.

I am a little bit older. As I started a company, I had a whole life going into it. It's less about integrating it and more about keeping my energy high with activities that keep it high. So, in a day, if it's all fundraising, that's actually very rejuvenating. But sometimes, I get more juice from product work, going through product stuff, analyzing data, mentoring, or coaching people. So, I design my calendar in a way that there's always rejuvenation. 

And how do you keep yourself accountable? It's easy to lose sight of everything when so much is happening. Are there ways you check in with yourself or others doing it with you? This is hard, and it's something I've been doing more recently with Randy, my cofounder, and my wife. Randy and I have been doing it every month or so.  

We have this scale that we copied from one of our investors—my old boss, Donald. You can rate your life on a scale of 1 to 5 in three areas: recreation (like play), meaningful personal relationships, and meaningful work.  So, for example, I might rate it a 3 at work—so then how do we get you to a 4? Or maybe it will be a 3 for the month, and you want to ramp up recreation to power through it. There's also, like, maybe personal relationships are at a 2, so how do we get you to a 3. 

But it's also acknowledging that it's never going to be 5 out of 5 and seeing what's the most important thing to move and how we can help you do that. The thing you want to avoid is stasis—if nothing moves. That's when I think people get upset, sad, or demotivated versus feeling progress. And it's just good to call out when things are going well and when things are going bad.

I love that. And it's an interesting and straightforward framework to try and apply for ourselves. Yeah, and it's just saying it out loud. A lot of people don't say it out loud. It's more about embracing the "okay, I have to grind this out in the next two, three, or four weeks. What can I do in the meantime to keep my energy up? 

For example, if my energy is at a 4, I may need to do a little bit more recreation because then I'm a little bit tired. It's like the athlete approach, right? They have time off and rest days and train hard for performance. There's stress. It's just about valuing your time and your body. It's like taking yourself seriously, and you're being affected by all these things and stuff that's happening. 

What were your decisions when you realized, "Wait, I should take the framework more seriously?" What helps you actually commit to using it more? Right when I met Randy, Randy had a lot of really good health and fitness practices like meditation and not checking your computer on certain days of the week. Whereas I came in much unhealthier than I thought. I had really high blood pressure and a high resting heart rate. I didn't realize how unhealthy I was because I was young and didn't feel it. So, over time, I changed aspects of very obvious things—I slept a bit more and drank a bit less. I was just slowly getting myself into a good, steady state so that when stress and stuff happens, my body can absorb it in a way that doesn't break my body down. 

I realized that these habits of drinking less, sleeping more, drinking less coffee, and exercising are all very basic things that I was not doing. That gets your body in a healthy default state. But all these activities' goals are usually to do more, not fewer things. So it's to do more stuff in your personal life to do more work and side projects. It's not about reducing yourself down to nothing. It's about giving yourself the capacity to do what you want. If I didn't do that, I don't think I could do as much as I'm doing now.

It's not about reducing yourself down to nothing. It's about giving yourself the capacity to do what you want. If I didn't do that, I don't think I could do as much as I'm doing now.

It's wild you answered this question in less than a minute, and it took me at least a year to understand what you shared. In particular, the word "capacity" encompasses time and energy. Personally, my health was in a poor state, yet I wanted to work super hard, and my mental health coach had to reel me back in by reminding me that I needed basic things like sleep and rest! And when I realized that, at the core of being a human being is health, sleep, and good food initially for somebody who might be going through it, it's tough to see that. But, it becomes so simple when you understand what it really means and apply it. 

I figured it out when I was 31 or something, right? laughing It took me a long time and a doctor's intervention. The doctor said, "your blood pressure is really high for a young man with no medical issues, and this isn't good. It took a lot of intervention and habit-forming to get my stuff to normal. It took over a year of behavioral changes, so it's not easy. 

But you also mentioned "energy" and "time," which I'm thinking about a lot. I realized being a founder is like an energy game, not a time game. It's not that you need more time but more focus and energy. And when you have high energy, there's enough time to do everything. With low energy, there's never enough time to do anything. That's why I talk about rejuvenation through recreation, relationships, or fitness—whatever you need to do to put more back into your tank. And sometimes, that's work. Sometimes, you work more to feel better about work, but you have to understand what it is at the moment. 

I realized being a founder is like an energy game, not a time game. It's not that you need more time but more focus and energy. And when you have high energy, there's enough time to do everything. With low energy, there's never enough time to do anything.

Why is the work you do important to you? I like being a founder because I think it's the best version of myself. It's forced me to grow really fast in very uncomfortable ways, face insecurities, and embrace what could be world-class. That's when people say it's the growth and growth of the company. It's personal growth, too. So I do really enjoy it. It's really hard, but it's also incredibly fun. That's the big meaning I'm getting out of it now. 

In terms of Merit, it's my life's work, and every day it's only more reaffirmed. But it just makes me realize how big the problem is. If I can solve this, I can feel happy about my time on Earth. I realized this is still a very personal thing to me. 

Are there any common misconceptions you want to dispel about being in tech or a founder? We can talk about tech. Most people are not happy in tech right now for various reasons—even though they're paid relatively well. Most people are employed, and a lot of people got laid off, but they'll eventually get their jobs back. I think people have this view of the world like it's good versus bad people. And I think there are heroes and villains, which is a good narrative device, but it's not that clear-cut. 

It's important to understand what everyone's incentive is. For example, when you talk to a VC, you need to know what their incentive is and who their boss is. Because it's not you, the founder. [VCs] answer to the people they take money from. To you, as a founder, it's a company, a mission, and a dream. But for them, it's an investment. And you have to think about how you would view an investment. And for your team, [as founders], we have to understand that this is a job to people. And while it can be some of the best work or the best time of their life and creating a social network...it's still a job. 

Once you [understand everyone's incentives], then you'll have a more honest dialogue with people versus thinking like, there are good and bad people, which there are definitely bad people in the world but less than you think. 

So I do think that when people talk about tech, like, especially in tech Twitter, it's just like a very naive view of the world where I feel like people understood the incentives of the people in the system; I don't think any of this behavior would be strange. It makes perfect sense how everyone's acting for the most part. 

It's also incentives in context. A lot of people outside of tech Twitter might not have the context of what's actually going on. So, while it's not a justification for what's happening, we recognize some things are less out of the blue than one would assume without context. Yes, and there's different empathy to which, like, Elon [Musk] is a weird guy, you don't have to agree with everything he says or does, but I also get it. I'm obviously not at that scale, but I get the pressure, and that tension [as a founder] can cause you to be very weird. Whether he's a good or bad person—that's a different conversation. Right, and honestly, I think that's less of an interesting conversation, personally. Judgment doesn't move people like you think it does. You actually have to change the incentives to get the change. 

Switching gears, what advice would you give to your past self—the one who just started what you're doing today? It's kind of dumb because we designed a whole mentorship platform but like "ask for help more." laughing 

Going back in time, when I started my career, university, and high school, I would tell myself to ask for help more. That's the big thing. Smart people like to ask a lot of questions and ask for help. So ask for help more. Lots of people want to help you. That's tough advice to take. I would give myself that same advice but don't think I would have listened!

Give us a list of three things you'd recommend. You choose the topic.

Here are three DJ mixes that I listen to help me to do things:

#1 For running: 

#2 For working:

#3 For chilling on a Sunday afternoon:

What's a favorite song or song you currently have on repeat?

Phoenix by Daft Punk. It's cool to listen to old music and be like, this could sound modern. I've been listening to Daft Punk, and it's very French Electro, Chicago House influenced. It doesn't sound outdated or stale. You could go to a club now and listen to that song, and it wouldn't sound old. It's from 1997. That stuff always impresses me. 

Enjoyed the Conversation with Kirk Fernandes? Learn more about Merit at get-merit.com. You can book a mentoring session directly with Kirk at https://www.get-merit.com/p/kirk-fernandes or follow Kirk on Twitter @k3fernan.

Kirk is also passionate about giving back to The Bowery Mission.  

The Bowery Mission exists to promote the flourishing of New Yorkers overcoming homelessness and marginalization by providing compassionate services and a transformative community. A donation was made to The Bowery Project as part of this Conversation.

You can support The Bowery Project by donating directly.

Donate to The Bowery Mission

Meet Jay Demetillo, a Filipino-American designer whose career and life spans worldwide. Having grown up in New York, making his first cross-country move to design in the early days of Silicon Valley, and eventually making cross-world moves to further experience and embrace living an international life. He shares his experience as he navigated his design career and the decision points that helped him expand his worldview while actively contributing to East and Southeast Asian communities.

Interviewed in February 2023

Heads up, the interview contains some explicit language that may not be suitable for all audiences. This conversation has been edited for clarity and brevity.

Tell us a bit about you. My name is Jay Demetillo. I'm originally from Brooklyn, New York. I grew up in DUMBO and eventually moved to Queens, then Long Island, with my family and sister because it got so expensive. 

Back in the day, I was an artist and was super into art. Then, I got into design and went to a design school called SUNY Purchase which is semi-upstate [New York], about 30-40 minutes up north. Once I graduated, I took a journey to San Francisco and worked for a bunch of tech companies. After that, I got jaded by Silicon Valley in general and left. I ended up teaching design in China for a little bit, then a few other universities and high schools. Afterward, I went to Singapore and was there for five years. That's where I'm at now, working internationally and enjoying every bit of it.

Did you always know that you wanted to go into design? I actually didn't want to be a designer. Culturally, my family is traditional Filipino. Most Filipino families will push you to go into nursing or anything in the medical field—or even hospitality. And I was not interested whatsoever. 

For me, I guess I was the black sheep in a way. I struggled because I wasn't sure what I wanted to major in. My first major was history, and then my second was creative writing. Finally, I was getting closer to what I wanted and eventually majoring in robotics which ended up with me taking a coding class.

We had to build our own websites with traditional HTML and CSS back in the day. A few people in the class were like, "Why are you in here? Your site is like being designed by a designer. You're not a basic coder." So they encouraged me to go to the design conservatory, and I got in and was very surprised. 

I hated [the design conservatory] the first year. But once I found out about typography, all the Swiss designers—I guess I fell in love. There was also a MoMa exhibit at that point in New York City and Cooper Hewitt [Museum] that got me super into design. 

So I was like, "Okay, I'm gunna hustle and make it my career as a designer." It was weird because, around that time, graphic design was seen as the dying profession, and it was going to be replaced by motion graphics. 

My first internship that turned into a full-time job was working as a live animation designer at Comcast. It was stressful because the timelines were completely different from being a product designer [today]. In the job, I was learning about time limits and good daily habits for working. The work would be like, "We need these changes by 3 PM tomorrow. Can you make those design changes tonight?" or "We need this animation video shipped at 9:30 AM in the morning. Can you work on it and ship it at 11 PM to DHL via a video courier?" It was crazy! So you're going through the grind of a traditional design job that was advancing toward work in animation and motion design. Yes, it was so stressful because I was learning on the go. But, what I learned there helped me with micro-interactions in After Effects. So I'm grateful for the experience.

I went to Silicon Valley after the [Comcast] job. I didn't end up at a traditional tech job at first—instead at Duarte, which is known for its presentation designs. So I worked there, but it wasn't my thing. 

It was helpful to learn how to present effectively, which I got to learn from Nancy Duarte, the CEO. The role helped me understand how to tell stories in presentations and ways to keep them simple. These skills carried through my career: for example, learning how to present, tell stories to different people, and actually design a deck. And most people don't care about how to design a deck. It's really hard to do! Right, and people just assume it's just a deck, and we'll copy and paste something, and that's it.

After Duarte, you transition to an agency next. Was there any connection in the work you were learning and growing from Duarte to the next role? For example, branding, since a lot of decks are branding. I joined them in general because the agency cared about the San Francisco community, and I wanted to do something community-oriented but also on the cutting edge of digital. This was also a small agency of about eight people, with six designers and two engineers. In this role, I got to learn how to work on UX.

Back in the day, no Youtube or Linkedin courses existed yet. There were no boot camps per se. This was the golden age where everyone's learning UX just by doing it because Apple had just released the app store where you could build your own app. The Android store just came out as well. So we were all learning, and it was awesome. 

We learned how to build apps with our engineers, talked to engineers about how to code things properly, and how to build responsive designs for websites, and ultimately it was just the beginning of UX. So I'm grateful for that experience because I don't think a lot of people had that.

And were conversations on figuring out what your role was or what you wanted to do and getting respected for your work also happening? It was a fascinating time because everyone in the Bay Area was focused on really nice visual illustrations on your website and how all these fancy new animations could be built with CSS. Or, even with WordPress sites—the focus was on making the designs more clean and organized. 

And to stand out, you have to be a really good visual designer. It's not just knowing UI but also illustration. Which is crazy when you think about it. Especially in the context of today, where there are specialized illustrators. Yes, but obviously, it helped that I did illustrations and whatnot. So, to stand out at the time, it was just, "how do you combine all your talents and produce things in projects that people see?" 

One of my favorite projects I worked on was for a restaurant called Gaspar Brasserie, where I did the website, branding, and interior design. I also worked with the architect and owner to pull together his styles and create a vision for his restaurant.

We looked at patterns and fabrics that were floral but also organic, which relates to the French nouveau style. It was awesome when I got to work with the architecture and even what the molding would look like in the restaurant. Alongside my design director, we got into the details of not only physical but also digital work. I don't think a lot of designers get to do that. And I wish, nowadays, that more designers got to do physical stuff because you can see that if you can design something that can translate into the physical world that goes digital, it can speak a lot about the story of a designer's experience in general. So that's why I appreciated projects like this.

And I wish, nowadays, that more designers got to do physical stuff because you can see that if you can design something that can translate into the physical world that goes digital, it can speak a lot about the story of a designer's experience in general.

And you mentioned that there was a point where you started to get jaded by the industry in Silicon Valley. Was it a specific moment, or could you describe how you recognized that was happening for you? For me, it's related to the [idea] of breaking the bamboo ceiling in a way. It's weird because I'll have conversations with folks internationally, and they don't believe it's hard for an Asian American or Asian person to break into the ranks of leadership in Silicon Valley. 

And it's unfortunate because when I was looking to level up, I was not getting those opportunities. So, maybe it was because of the situations I was in at certain tech companies, or it was just not how things worked out. So, I was like, alright, maybe I just need a different change of scene. And maybe I just need to try something else. 

This opportunity in Singapore came up, and I was like, "yea, why not?" I figured they needed help and guidance, so I ended up going in. 

What also pushed me into [taking the opportunity in Singapore] was that me being Southeast Asian and Filipino, there's something nice about giving back to the community and knowing that the company I worked for in Southeast Asia was directly impacting the community there, whether it's good or bad. So I rolled with it because there's always a pro or con with any company you work with, but as long as you see the impact can be positive, there's something meaningful about that.

Were there any particular moments that stuck with you or helped contribute to the decisions to really pull the plug and say, "I'm going to take the leap to design across the world?"  The entire time I was in San Francisco, I volunteered at the Inneract Project. Seeing those kids react differently to folks of color, especially showing that there's an example that you can make it, definitely made me think that I'm glad I can be a representative. 

Still, I'm also thinking about my own roots in general. I wondered how I could also become a representative for folks in Southeast Asia. When I worked at these companies, I wondered, "where are all the Asian leaders?" I would get into arguments with people because I'd ask, "what do you mean there are so many Asians?" There are a lot of generalizations that there are a lot of Asians in tech, but really, there are not a lot of Asian leaders in general. You could probably name only a few leaders off the top of your head, right? And that's unfortunate, especially if you're a Southeast Asian. You don't have a lot of role models.

When I was teaching at CCA (California College of the Arts), many folks from China studied there. And then also, when I taught in China, I noticed there weren't a lot of role models for designers to look up to. It was fascinating because they all looked up to Japanese or Western design styles, often focused on being minimal. I get it, but I also started realizing there may be colonization with design. Even as I studied design in school, the names we often heard cited were people who didn't look like us. So I always wondered, besides representation, it's also about exposure. The people who had power and access to a broader audience to share their thoughts just weren't possible for people who looked like us.

Around this time, I also started to see the rise of design leaders in the space that was often very well-known—whether that's because they were in leadership at a particular company or were very big at conferences and online. We weren't quite in the era of design influencers yet, but it was just about to start. Did you also experience this? I started seeing more design leaders online when I decided to leave Silicon Valley. I was so glad I left because it felt like it was getting a little bit much. I'm not trying to throw shade at anybody; everyone is entitled to celebrate themselves. Everybody should also celebrate whatever achievements they get in general. 

But, I will say that there are people that I've worked with that I've seen often post on social media and are well known in the space, and when you work with them, you're just like, "huh, I expected a different type of level of seniority." Often, people say they've done stuff publicly or online, but they didn't really work on it or have the actual experience. So, as a result, their output doesn't meet your expectations. 

Jay Demetillo recently spoke with Harrison Wheeler of Technically Speaking on East vs West Working Culture and the Bamboo Ceiling.

For me, while I do care about reputation, I care more about making sure I don't post things that are unintentional. I want to be intentional with everything I do, including talking to you for west & ease, and having meaningful conversations with the people that mean a lot to me rather than just posting random crap online. I also want to post more to ensure more role models speak up, especially as additional representation for Southeast Asians.

I recently had a conversation with a friend where we're starting to see the rise of the Southeast Asian tech scene and designers. Tech and design haven't been practiced a lot there, and now technology is finally caught up. The rise of design is being celebrated in Southeast Asia in general. But, there hasn't been enough writing, books, or focus from the rest of the world. So that's why it's good for me to be out here and celebrate those designers. 

I don't want to say I'm part of that change. I don't take any of that. I'm more or less trying to help shift the perspective to being that there is great design everywhere in the world and not just in Silicon Valley or Europe.

After being in Silicon Valley, you left for Singapore. When you got there, did you start to see a shift in the types of people prominent in the design space you were now in? Especially since it's both culturally in a different space and physically in a different location? That's an amazing question. When you move to a different country or new region of the world, you find out who the experts or tastemakers are. That's when I found all the different types of people I had been missing out on, which is fascinating.

The weird part is that it's not a generalization, but culturally, Asians, especially in Asia, don't try to make things about themselves. The culture is not very individualistic, like Silicon Valley or generally in the Western culture. They care more about the collective as a group.

So if you were to try and stand out, it's looked down upon. I appreciate that, and there's something to be said about working as a team, especially in the design and tech field.

And, of course, you can tell some people stood out that are very gifted. And one of the things that hinder them from being big is the language barrier. I often talk about this in my talks, where speaking English doesn't mean intelligence whatsoever. These folks are very good at speaking their language, whether Indonesian Bahasa or Korean, etc. There are many talented designers, but speaking English or even posting something hinders them potentially because not a lot of people can read or understand what they are saying. And that's unfortunate because there are so many talented people out there that they should be celebrated. They should be held in high regard, but they won't be hired at places like Apple or Google because they can't pass the interview with their language barrier. That's the unfortunate part. And that really sucks because it closes us off from an enormous amount of talent and potential around the world.  

I think it's important for me to be inclusive. In general, I don't think the design community on social media or on the Western side is inclusive of different cultures or other designers from different cultures. 

You even see it at conferences or talks. Where are the people from Tencent design speaking? Where are the people from Grab speaking at these events? There are so many good startups in China, Hong Kong, and Taiwan. 

For me, I want to make sure that wherever I go, I hire an inclusive team. I hire people based on potential and talent, not just because they can speak English or whatever, right? So it makes me think about how do I grow my team? How do I make sure that I become a good leader that takes all these things into account that I learned not just from Silicon Valley but also working internationally?

I'll talk to managers in the design world, and often, they've only worked in Silicon Valley. They don't know how to handle different cultural backgrounds because everyone works differently. I had to adjust big time when I moved to Singapore. For example, the whole radical candor goes out the window. You can't be radically candid here; you'll be dragged! laughing It's a totally different beast.

And so, for me, the things I took away from working at my past company [in Singapore] are now things I want to make sure are still in the culture I make or the team I'm going to make going forward wherever I land.

More importantly, I want to make sure that the people I work with represent my beliefs and culture but also empower folks to make sure they can stand on their own two feet—whether they stay in Southeast Asia, APAC, or go to the West and vice versa. 

As you were speaking, it reminded me of a recent conversation with a colleague in Chile. She asked me, "how do you, as a product designer in the United States, design globally?" It was a hard question. We don't think about it as much as we should because we want to build at scale—but everything tends to be very Western-centric. And that's a big hindrance to how we approach problem-solving because I'm unaware of cultural nuances. Luckily we have many global colleagues we can lean on, but wouldn't it be more powerful if I could work in many places worldwide to help inform how to approach design problems differently? It's real. On top of that, we don't realize how much privilege we have, especially working in Silicon Valley. We don't realize the impact we're making until we see it on the ground.

Why do you think the work you're doing is important? For me, it's realizing that your career doesn't define you. Yes, I've done a lot of cool stuff; I've moved everywhere. But for me, it was because I wanted to try different cultures. I wanted to live in different parts of the world. Maybe I'll move back to the [United] States, but I don't know. I needed a different perspective on living in general. 

I want to live a life that's fruitful, and I don't want to just depend on a tech job to carry me through. And while, yes, I've already gone to another tech company, at least I'm living in a different part of the world, trying different things. And at least, when I'm old and gray, I can look back and tell people that I did try. And I did push the limits of getting uncomfortable to get comfortable with the way I'm living.

So, I think your career doesn't define you; it's just how much you want to push yourself to try different things. I've done digital nomadism before, and it's amazing. But a lot of people are scared—I get it. We get comfortable with the pay we make, right? The golden handcuffs are normal. But once you leave that, you find out that there's more to see and to do. You start realizing that tech isn't everything and there are a lot more meaningful things than just your job.

So, I think your career doesn't define you; it's just how much you want to push yourself to try different things.

It's often a difficult decision to make the move to prioritize yourself over your job. Do you have advice for those who are on the cusp? Of course, everyone has nuances and circumstances affecting their decisions. Part of it is a privilege. In terms of my social-economic status, I did have the capital because I worked my butt off for that capital, right? It wasn't because it was handed to me. 

I think you just have to plan it and plan it in advance. For me, it was like, "okay, I'm going to quit my job this year because I have enough capital to do this and the privilege of this and just live."

In terms of advice for folks, right now [in February 2023], it's not a great time probably. If you've been laid off or going through a lot of financial hardship, it's a bad time to do that. But, to be honest, a friend that's a business owner shared with me that you just got to change your perspective that your debts can be paid off. It's how you handle that debt mentally and how you want to live your life. Things eventually work out.

People have a hard time letting go and have the restraints of that lifestyle that they potentially have been living in on that large paycheck. So maybe it's not good advice, but for me, I think that debt goes away. It's not the end of the world. Bankruptcy isn't the end of the world either, especially if you're a business owner. And I've talked to a lot of business owners. It's not the end of your reputation, either. It's just a fact that it happens.

And for right now, the layoffs are cyclical. This has happened before, and jobs have come back. Everyone's even scared about AI because now all these new apps are coming out. But if you think about it, they still need people like us to build stuff out. And AI—it's just a tool. It's just the tool to ideate faster. So I don't think we should think about limiting ourselves. We need to expand outside our mental state, which is hard. That's hard to do, but once you do it and find out that you can do it, it changes a lot of perspectives, like once you get out of that system.

And you start living the life of maybe hiking in the jungles of Thailand. It sounds so romantic. But what about living off the country in the Midwest? That's definitely doable if you're in the States, right? I've seen people just quit their jobs and do it. They live on a farm, and it's awesome. They love it. So whatever is fulfilling for you, and you want to do it, just try it. Why not? Do it for three months and take a sabbatical, and things happen. You can't control the economy, but you can control your life.

So whatever is fulfilling for you, and you want to do it, just try it. Why not? Do it for three months and take a sabbatical, and things happen. You can't control the economy, but you can control your life.

If you already have the idea to try a more nomadic lifestyle or even leave your current role to start planning, and through the research, you can actually realize it's actually possible? It's definitely a mindset as well because, for someone as risk-averse as me, it's hard to take that jump, but once I do, I will experience the magical parts of things working out. I definitely agree.

Are there any misconceptions about you that you want to share? Yes, especially since I do public speaking, where people think I'm an extrovert. I actually like being by myself a lot. That could be partly because of Covid-19 [pandemic]. When I have large parties, I like to just get away for a little bit and have time for myself.

I realized that I just enjoy hanging out at home. I don't want to stay out late. I still go to concerts and go out in big groups, but I don't like it. I would rather connect like this one-on-one and be blissful about it. 

Is there any advice you'd share with the past you? Well, I'm already resilient in general. But, I wish I could have told myself to be a little bit more open-minded in terms of knowing that there are going to be different cultures involved in my daily life. And that I probably should have appreciated that when I was younger. And I wish I did.

Because now I appreciate [different cultures] so much more. When you're a kid, and your parents take you to different countries, groups, or places, you don't realize or know that. You're just like, "I don't care about this," and being a little jerk. But, then, you realize when you get older, it's like, I should have probably appreciated that a little bit more than I should have because those days are gone. And you can't recreate it.

I wish I had taken more time appreciating those times with different people, family, and cultures, and because now that I'm international, I wish I had more time to spend with those folks.

I would have told myself to go chill and appreciate this because you don't know what's in store for you in the future, so you should probably appreciate it a little bit more. Though, now that you're older, you're definitely more intentional.

Give us a list of three things you'd recommend. You choose the topic.

I actually have five things. 

1. If you're a designer, go to the Basel Summer Workshop in Switzerland. Classes are amazing for anyone, and I want to go back. 

2. Paragliding in the Alps. If you're not scare of heights. I've done it twice!

3. Travel! If you're in Vietnam, hit up Hanoi and Saigon. The food is amazing. 

4. Visit the Philippines, especially Palawan beaches.

5. Visit China. People are so nice, and they're so grateful for visitors in general.

What's a favorite song or song you currently have on repeat?

I'm a big music nerd, and I like to shoot concerts on the side. So I've been listening to SZA's new album, SOS. And Joey Badass's 2000.

Enjoyed the Conversation with Jay Demetillo? Learn more about Jay on Linkedin and Instagram @asianxjay.

Jay is also passionate about giving back to Inneract Project. Inneract Project is a 501c3 non-profit organization working for over 18+ years to empower the next generation of Black, Latinx, and underrepresented designers of color. As part of this Conversation, a donation was made to Inneract Project.

You can support Inneract Project by donating directly.

Donate to Inneract Project

Meet Red Gaskell, a Filipino director and photographer based in Los Angeles. He runs RG Studios, a production company focusing on branded content, commercials, feature-length films, and documentaries. He shares how he got started in the production world by diving into freelance and sharing his learning process with others. Along the way, he's found satisfaction through the ability to collaborate with friends and hopes to continue to do so as he explores the world of directing further.

Interviewed in December 2022

This conversation has been edited for clarity and brevity.

Tell us a little about you. My name is Red, and I'm a director in LA. I'm also a photographer. Short and sweet.

Can you share any career-defining moments of how you got to where you are today? There were several moments.

My first career-defining job was doing social and making all the content at Everlane. When I was there, what I was doing was mostly just on the phone, so it wasn't "real production." But I got to do a lot of the behind-the-scenes on set. I would learn from photographers, directors, or people they hire to make things for the website or the campaign. And I thought, "I could do this." But there wasn't a path for me to do it internally [at the company]. 

So, I started freelancing [full-time] to figure out how to get into production and get hired for that type of work. But instead, when I started freelancing, I would get hired for social media content.

It took me going back to [in-house] full-time work but negotiating that I would get to do something so that I'd be able to put in my portfolio that shows actual production. So, even though I got hired for a social and marketing role, it helped me get that first piece of work I could point to when I started freelancing to show, "Yeah, I can do this."

Often, people in their careers want to transition to something else, but it's tough to do so. How did you get your new job to agree to give you that chance? Or how did you help the team see the potential in you? It's a little biased because I had such a good run at Everlane that I got lucky. I had a lot of leeway in choosing the next opportunity. I couldn't go straight into production, though. Or I wasn't confident enough to ask for that. Maybe more people would have given me the shot if I had asked for it, but I didn't.

People were impressed with the run I had [at Everlane] and what I did while I was there, so they were willing to give me opportunities, even though sometimes it felt like I was pigeonholed to social content. Or I’d be recommended for something where they described the ideal candidate as young and hungry which is a nice way of saying someone desperate that they will underpay.

I also had a good relationship with the founders at this new company. They believed in allowing me to pursue other creative avenues while doing this other role, so it worked out. I think a lot of people wanted me to succeed though, and felt like there was always someone looking out for me. And there was a lot of luck.

There's always a lot of luck. However, I want to touch on the other point you mentioned: you could have gotten more production work earlier if you had asked. What do you think held you back? It was myself and not having the audacity to ask. I could have, but I just didn't. And I think I was probably afraid of not making money. I didn’t want to be broke again and start from zero.

I was [still] pretty audacious because I interviewed with a fashion company: an Amazon-owned, direct-to-consumer brand trying to do basics and stuff. I had quoted them a crazy amount of ~$60,000 for three months of work for just strategy or something like that. And they were considering it, which was shocking to me. But the person I was talking to left the company, so that didn't really pan out. 

Through those conversations, I thought it was interesting and couldn't believe they didn't straight up say "no." But yeah, I was staying in my comfort zone of social-related things versus trying to make commercials and stuff at that time.

So from this full-time role, you went back to freelance afterward? Yes, I went back to freelance afterward. I was in that full-time role for about eight months. But I did try to quit the first day. 

What happened? I was already hesitant about joining a company full-time. I was doing a lot of freelance for Airbnb and some other companies, which was really fun. I just returned from a trip to Mexico City, where my friends and I filmed an Instagram story about some Airbnb experiences and all this cool stuff. So I was like, "oh, this would be really cool to do around the world," or something like that which they were discussing potentially. 

But, the full-time role offered stability, predictability, and really high pay. This was the first job where I negotiated for a lot of compensation that I felt I wanted and deserved. So I was like, "maybe I should do this." I also wanted to freelance, but you can't do that at a startup because it'll take all your time.

When I got there on the first day, I opened my laptop, fired up slack, and I thought to myself, "What did I just do?" 

Next, I contacted the HR person or the person who helped hire me, and I was like, "I think I made a mistake. I'd like to quit." laughing Oh my god! So they contacted the founder, and since the founder was on his way to the office, he asked, "Can we just talk real quick?" The conversation turned into three hours. 

He convinced me I should stay for three months through the launch, and then we could revisit my decision. And, I guess I folded. I don't know what would have happened if I had quit, but I decided to stay full-time for eight months. I got all these things that felt important at the time like a nice salary, benefits, options etc. I started making friends at work and just began falling back into the full-time routine. 

In hindsight now, what kept you going in those eight months? What kept me going was that I would be able to shoot all the e-commerce and launch videos because the company hadn't launched yet. With the big launch, they said they had all these relationships with magazines and editors, and the videos would be released as part of that. I figured it would be a good opportunity to make something with some substance in terms of the campaign, launch, and everything—which was enticing. And to be real a full-time salary and benefits is hard to leave.

Were there other decisions or factors you considered as you transitioned to the next thing after this full-time role? More opportunities for actual photo shoots, like editorial and styling, would have probably made me want to stay more. If we were doing a lot more conceptual things and videos but those things weren't happening. In hindsight I probably should have joined a company with a strong production team already in place or an agency or something where I could learn. But this was still a startup that just launched, so we were figuring out tons of things meaning we had to switch focus a lot. I couldn’t go deep on production even if I wanted to.

By October I was pretty burnt out and hit my tipping point and, one of my closest friends, Dinesh, told me that his friend's family winery wanted to do a documentary about the harvest they're doing in the fall. And I was like, "I'm so in!" They also had a good budget that allowed me to quit almost immediately and take on this job. I had saved money, too, so I was in a good position to be like, "I think my time is more important than anything else at this point." And it was now, or I'd be [at the full-time role] for the next three years.

The winery project gave me a lot of confidence. They were also a really good client because they paid the 50% advance and paid on time. They treated us so well. And they set a high bar for any future client.

Aside from that, I was filming anything with any friend who wanted to do something cool. 

My homie Chris aka Honorroller built these wooden sculptures for a skating competition and asked me to film his process and record a short interview. But he said, "you don't have to edit any of this; hand over the footage to the skate company hosting this competition, and they'll edit it together." So all this footage and his interview were sitting on my hard drive, and I wanted something for this because it was cool and I had a lot of built up creative anxiety at the time from not making anything. So I cut it together into a one-minute episode, added music, and just a fun little edit showing his process. And people really liked it.

And it's something I want to revisit because I want to do more of that: short video portraits of artists and friends. 

[The video portrait is] what got me an opportunity with Square, which led to two documentaries—one of Chinatown in New York and one on a Filipino family in New Jersey. [Square was] focusing on small businesses, and they wanted to film a couple of these video portraits of small businesses in New York and New Jersey. But, the initial conversation was happening around February 2020 when I released the initial [woodworking] video portrait. 

My friend Nick [from Square] was like, "This [video portrait] is cool; how much do you think it costs to film something like this?" And honestly, I had no idea. But I looked at the company Square, and I was like, "they're a bank!" laughing They have money. And I was like, "I guess one or two of these videos will be around $40,000 for the production budget." And he said, "Sounds about right." And I was like, "Holy shit." 

I later learned that a production budget that's $40,000 is not very much money since it gets divided very fast because of fees and other things you have to consider. So that was February 2020 when we had that initial conversation. And two and a half, three weeks later, he said, "Hey, we're shutting down [because of the Covid-19 pandemic]. So we're not doing any production for the rest of the year." 

So even though in [2020], I did a lot of filming at home in my apartment, like product videos and stuff, it was strangely good because many companies couldn't have too much overhead. And I had no overhead. So I filmed stuff in my apartment and started doing self-assigned homework, like recreating movie scenes or an image I liked. For each, I gave myself limitations. Those also did well; people thought they were good, so they'd later hire me for a client project.

Could you walk us through some of these self-assigned projects? The first one I did was a scene from Parasite. I was binging movies and had a bunch of food and booze on my coffee table. And I was like, "This already looks like the scene. So let me adjust a few things." And I had a dark gray couch that looked like the one in the movie. So there's a little production design to that.

For the next one, I tried recreating the scene from In the Mood for Love, where Tony Leung is smoking a cigarette in his office. I went out and bought clove cigarettes. I burned incense to add more atmospheric smoke.

Then, I did another one where I recreated a scene from La La Land that looked pretty damn close to a scene from the movie. I already had a piano since I was trying to learn to play during the pandemic, so I was able to use that in the scene.

I also tried recreating an Apple iPhone unboxing commercial. The entire [original commercial] was shot in an apartment, so I was like, "this is perfect." That was interesting because I learned how to do the visual. I got close to doing it like the scene. There was one scene I couldn't do because they used a robot and a special lens. But I did everything else. I also learned that sound and music are so important because that was half of the video and what sold and made it feel like a really good commercial.

So those were some of the projects that got people's attention and made them think of me for stuff. I’d get hired and it kept me going throughout the year. 

What did you focus on next? After doing stuff by myself, I started doing things with my friend, Keith. We wanted to recreate this sketch that Kevin James did of a simple interaction where someone is waving in your direction, and you think they're waving to you. But it was meant for someone else behind you. And there's this misunderstanding, like, "oh shit, that wasn't for me, and I'm embarrassed."

So we recreated our version with some friends who acted in it. We did that in a day, but didn’t release it for almost a year because we couldn’t get the right music for it. Until I asked my friend Yuri and he turned something around in 1 take and it was perfect. When Keith posted it, it got a ton of  comments saying how good and funny it was. And I realized, "oh yeah, I like doing this stuff." We didn't get paid for it, but it was the quality that people thought was good. And so we wanted to do more of this.

Then, a few weeks later, he was producing a couple of videos and a photo series for Nike. The people he was originally going to work with had to drop out. So he's like, "I guess the universe is saying we should work together again." 

At the time, there were two markets for video creation. One of them was a DSLR where you're filming like Casey Neistat or shooting a lot of concerts with fast editing. It felt very competitive. So, I had to find a way to separate myself from it, and I thought, I'll get a cinema camera and enter more of the production world where there is a team and more people that'll give me a competitive advantage.

So around the same time [that Keith wanted to work together], I had just bought a new camera. Initially, I was looking at the camera and thinking, "Can I afford this? Is it a good idea?" I had really good credit, so Sony gave me 0% financing over the next four years, which was ~$200 a month. And I'm like, "Okay, why not?" And I can also rent the camera out, so it'll pay for itself. You know how when you want to do something, you'll figure out a way to rationalize it to make it make sense even if it doesn't? So it made sense. 

I got the camera and felt like, "Okay, cool. Let me do production stuff now." And so he hit me up, and it felt like a good opportunity to start down this path. We made a couple of things, but honestly, it was too soon for me to start using that camera because I didn't fully grasp how to use it to its full potential yet. We did good and filmed a lot of really good, beautiful images. But, I think it might have been better for me to use the camera I already had and knew well because this production was still pretty much figuring out a lot on the fly from location to location.

There were some things I was really excited about, but there are definitely some things I wish I could have done better. 

This was also when I was still really afraid and not confident, but my big bet was to say "yes" and figure out how to be as helpful and useful as possible. What will make my friend look good to Nike or make this a really good production? And if I bring really great equipment with me, like the camera, drone, and accessories, it'll be really useful. But, I was a one-man camera crew, and the technology and gear ended up getting in the way versus having a simpler setup. Now I know better.

As someone who has been following your journey, I found that not only did you share the final work you've done, but you also invited your audiences and friends to be part of the process with you as you figured out how things are made. Were you conscious that you were doing a lot of sharing to get more visibility, or were you like, "I'm just going to do this and see what sticks?" More of the latter where I'm just going to do this and see what sticks because there was nothing else to do [during the pandemic]. And I get creative anxiety if I sit around too long. So I needed to do something, and for some reason, it felt like the right thing to be working on. And then I would see feedback and be like, "People are into this, cool. Let me do more." I also spent a lot of time answering questions in my DMs about this type of work. But then, one of the reasons I stopped doing it was that I didn't want to be known just for that.

Some people have really good work but have no social media at all. And I used to think that my social media would create opportunities for me, but I realize that doesn't need to be so true anymore. And I wanted to avoid getting caught in a cycle of doing self-assigned projects and answering questions in my DMs. Instead, I could be doing something else to pursue more opportunities. 

Some people have really good work but have no social media at all. And I used to think that my social media would create opportunities for me, but I realize that doesn't need to be so true anymore.

What happens next? It's the end of 2020, and I'm starting to think about what I need to do in January, who my clients will be, and putting together a reel to reach out to folks. Then as January is about to end, Nick [from Square] hit me up about budgets rolling over from this past year, and that we could work together on something. That was exciting.

We got started at the end of January [2021]. That project kept me busy through June. I'm so grateful for that project because that was my first step into a big production. It was the biggest budget I had worked with at the time. I got to hire a crew. I also got to work with another production company showing me the ropes. I got to work with an incredible producer that my friend had also worked with.

This was the turning point. That was the first project I started to understand, and I can keep talking about this for years. The shelf life of it is so long. Before, when I worked in social, you were only as good as your last post. And it doesn't stand the test of time. Some things may go viral, or people like to look at them, but it's short and few in between. Yeah.

I still get to point to it. And even this year, I'm working on something because of that project. But all in all, the Square projects went further than I could have imagined. They got into several festivals and won awards. We got into Tribeca X, the advertising part of Tribeca, where we were finalists. I was shocked by it, and it was super cool.

With this turning point and the time then till now, have you started accomplishing what the past you set out to do when you started this journey? Yes and no because, honestly, I thought, "Oh shit, this is it! I'm going to be doing this all the time now." And that didn't happen. 

I've been bidding a lot, getting considered for opportunities, but they'll fall through, or clients pick a different director. I've talked to other directors about this, and they say, "Welcome to the life. That's just part of the process." One director, Ryan Booth, who’s helped me a ton, shared that if you're batting 300, you're killing it. If you get 30% of the opportunities you're considered for, that's a good thing. Someone else clarified it for me: most people will get one really cool project a year. And then the rest of the time, they're doing projects that'll pay the bills, but they'll probably never share that. 

There are a lot of comparisons and anxiety because, on socials, it always feels like someone is on set doing something really cool and you're not. I also try to balance it out because there's more than enough work. After all, these brands and companies are constantly making stuff. I try not to fall into that trap that much and remind myself that I need to be patient since I only really started in 2019. So, I'm doing pretty well in that regard. Many people I know doing the work I want to do have been in the game for ten years or more, so I can be patient.

Why do you need to bid for projects versus creating your own? Could you share that process a bit more? For commercial directing, clients want you to audition yourself and convince them why you're the right director for the project. They're going to hire people based on something other than just their previous work, like applying for a job. The process usually includes the client sending you a brief, and they want you to create a treatment and a document that is personal and creative and tells them why you should be the one to do it. You have to be very charismatic on a call where you present this deck and tell your story. 

So there is a lot that I'm learning about because I presented a couple of times earlier this year and got feedback on needing to work on a few more things. For example, I'm good off the cuff, but then I tend to ramble sometimes, so I need to cut down here and there. I even took acting classes because I'm trying to figure out how to speak more confidently, especially when given a question I'm unsure about.

I'm working on those skills now, too, because it's not just about my technical skills. In the past, it was figuring out the technical parts, like how close I could get to what the big leagues were doing, and I could get 80% of the way with limited resources. Now, it's more soft skills and a sales game. And knowing myself, my story, and how to present myself is a new challenge.

You also mentioned you're a photographer. You've recently been focusing on a personal project of doing more portrait photography. Why is that important to you? As a director, I'll work with actors, but it's hard to do video scenes every day. So photography is a shorter, faster turnaround way of working with people to direct them and create the image and feeling I want. There are a lot of soft skills in photography—clicking the button to get the shot is the last 5% of it. The bulk of it is communicating with people and making them feel confident in what they're doing as you're about to photograph them. It feels like a good skill to develop for filmmaking. 

It's also something I'm personally interested in. There are a lot of photographers I admire and want to be able to shoot photos in the same sort of way. I want it to be a skill that I have. I've always been naturally okay at interiors, still life, and objects. People are scarier because it's more than just sitting there taking the same photo of a corner or chair and adjusting the lighting. It's doing that with a person who is present, and you have to consider them and their energy, emotion, and feelings too. 

People are scarier because it's more than just sitting there taking the same photo of a corner or chair and adjusting the lighting. It's doing that with a person who is present, and you have to consider them and their energy, emotion, and feelings too.

Now that you're a few years in—why is it important for you to continue what you're doing? It's creatively satisfying. I like the collaboration in filmmaking. I also enjoy the solo work, so it's a bit of both. It has to do with being in the creative process for yourself. We talked about this earlier. It's not so much about the result but knowing that I can do this or the process of figuring it out together. 

Earlier today, I did a portrait shoot with some of my neighbors in my building. It was really fun because they were like, "We've never actually had our photos taken before." This was a new process for them. And I was like, "This is my studio's third or fourth portrait session so I'm learning too." And there were a lot of things we wanted to try together. They pulled some images they liked, and I had some references in my mind and what I thought could be cool. And so, we were just figuring it out together. There's just something about the craft of it that was really cool.

Even recently, I went to an improv show at the UCB Franklin Theatre, and it was really fun seeing people go through the process of getting on stage to perform. I got drinks with some people after and learned about what they do, why they do it, and how. I'm just drawn to that sort of thing. 

There's a lot of satisfaction in it too. My friend Tiki and I did a project earlier this year for a mental health startup. We came up with some reference images, and there were a lot of things I wanted to do. We had a limited budget and team. Tiki recognized an opportunity while filming on the beach as the sun went down. He said, "If we go up on this hill over there, we could get something close to the thing we wanted in the mood board." And it was spot on.

I was so happy because it looked just like the thing I wanted to do. I was like, "Thank you. This is amazing because I was so focused on what was in front of me that I wasn't even looking around the area." Having a solid team of people that are looking out for you is so important. And it’s mad nice if they’re your homies too.

Switching gears, any misconceptions about you, the work, or the industry you're in? As an outsider, when I think of directing, I think of this lucrative career to be a director, and it's super fancy! Film production is the least profitable freelance career possible because there's so much overhead. People think that if we charge $100,000 for something, we're making $100,000. But you have to pay the crew. Then, if you pay everyone on payroll, 23% of that is going to fringe and taxes. 

And then, I also pay myself a salary now. When I pay myself, for example, $10,000, it will cost me $11,000-$12,000, and $4,000 is already taken out for taxes. When it goes from the business bank account, $11,000 gets taken out, but only $7,000 ends up in my personal bank account. So, it's not very lucrative. But then again I guess I’m doing okay if I can pay myself $10,000. Don’t get me wrong though I’ve set up a salary so I’m basically at $75k a year. 

I figured out a way to make it profitable enough for me that I am running a healthy enough business. Much more planning is involved, especially if you're a business owner because I have a production company. I'm not just a freelance director. I think I could be, but it’s scary. I have a lot of good direct-to-client relationships and that's kind of my comfort zone right now. 

I’m definitely doing more work now than when I was a full-time employee and I have to do more of the work I did not like but it’s different here since it enables me to work like this. 

Are the direct-to-client relationships what you'd rather be doing? I don't know. It's only been two-ish years, and so far, they've been really good because that provides a lot of stability. In the next two to three years, there's probably a future where I don't do the infrastructure and overhead. It would maybe be better for me to work with a bigger production company where they have relationships with agencies and brands for these bigger budget projects, and then my day rate increases. Right now, it's more financially incentivizing to work on direct-to-client relationships. And that's what works for you right now. 

Another misconception is that people often think being a director is a creative role. But there is a lot of admin, management, and spending a lot of time in Google Sheets and meetings. There's a lot of that. Of course, you're running a small business by yourself!

What advice would you give to the past you if you had the opportunity? I don't know because it all worked out pretty good. It's like the butterfly effect; I don't want to jinx things. And have a solid group chat, shoutout to Bag Talk.

Okay, maybe not actually go back in the past to say it, but general advice for yourself? One would be patience. And then I wouldn't have quit my first job at Everlane so soon. I did give them three months' notice, but I may have tried to do more projects on the side.

Another thing could be calming myself down. Probably spun my wheels a lot unnecessarily. I was anxiety-ridden all the time with what I did. I felt like each opportunity would be "the thing" that changes everything. It isn't. It's an accumulation of those things. It happens fairly gradually. There isn't an overnight thing. And I'm still in the process of getting there.

I felt like each opportunity would be "the thing" that changes everything. It isn't. It's an accumulation of those things. It happens fairly gradually. There isn't an overnight thing. And I'm still in the process of getting there.

I have the project with Square, but I'm still struggling to figure out my next major directing thing, which I'm getting now I think. I just signed a contract for something new to go to Argentina, Brazil, and the Bay Area next year, which I'm really excited about. 

I didn't get a lot of these other opportunities this year [in 2022], but it's fine. I survived. Actually I did more than survive. I did work I'm really proud of, and now I have a project  that instead of four, five, or six projects to complete in a quarter, this is the one project I will work on for the next three or four months. And that's okay. And that's okay, and it's exciting!

Give us a list of 3 things that you’d recommend; you choose the topic.

1. Tsubaki in Echo Park, LA. It's a Japanese restaurant that does yakitori. They have this short-rib dish with carrots and potatoes (short ribs nanban-style) that's really good. The chicken oysters (soriresu) are also really good.

2. Pizzeria Bianco in LA. The chef was in the first episode of Netflix's Chef's Table Pizza Edition. The pizza and they have these mortadella sandwiches that I've been craving since I had one in this place in New York. It's just so good.

3. Two things: Ryan Booth's podcast, The Process Dispatch, and Off Camera Show with Sam Jones. I've been listening to and watching the interviews that are so inspiring. You get to hear about the early stages before these filmmakers blew up who are riffing on their entire careers. It's been helpful in giving me the context of what I'm doing now in these early years of pursuing this path. It's made me feel less like comparing myself to people who are already working at a high level. Learning that they have to do these things too! And that I shouldn't feel bad that I'm losing all these jobs. They went through these slow periods or whatever too. And it's just like, "Okay, like, it's not that bad." There was a point where they didn't give up and it got better.

What song do you have on repeat right now?

Tops, which is a Canadian band, my studio mate, showed me that I've been listening to all day. That, and the Red Hot Chili Peppers.

Enjoyed the Conversation with Red Gaskell? Learn more about Red at redgaskell.com and his production company, rgstudios.co. You can also contact him at red@rgstudios.co

Red is also passionate about giving back to Heart of Dinner. Heart of Dinner’s mission works to directly address food insecurity and isolation experienced by Asian American seniors in New York City. As part of this Conversation, a donation was made to Heart of Dinner.

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Meet Ashley Woodfolk, a Brooklyn-based mom and a full-time award-winning writer of books for kids and teens. Ashley shares how her interest in children, books, and writing has driven much of her decisions as she navigated her life and multiple careers. From teaching to successfully publishing her debut novel, The Beauty That Remains, while working in publishing, to now as a mom and writing full-time, Ashley has learned to hone in on recognizing her strengths to make her voice and contribution to the world stronger.

Interviewed in December 2022

Heads up, some explicit language in this conversation might not be suitable for all ages. This conversation has been edited for clarity and brevity.

Tell us a bit about you. I'm Ashley Woodfolk. I am a mom, writer, and contributor to society. I want to leave the world a little bit softer than before I got here.

How did these parts of your identity start to take shape? As far as being a mom, I have always wanted to be a mom. I've always been a very empathetic and compassionate person. Those characteristics lend themselves really well. So, it was always something that I wanted. But when I wanted it before, I wanted it in a very selfish way. 

Now that I have a kid, I want another one in a different way. I want it because I can help make a person who will help others. And so I feel like, when I was younger, I was like, "Oh, I want a kid because they'll be so cute, and it'll be so fun to be a mom." But it's much more work than I fully understood. 

There's now much more transparency about motherhood and what it's like. When I was younger, that was not really a thing. What do you mean by transparency? As a society, the zeitgeist has come around to talking about motherhood in a much more truthful way. Whereas when I was in my 20s and thinking about the possibility of becoming a mom, nobody was talking about it for real or being real about it. It was still very much like, "Everything is beautiful. Motherhood is such a journey." And it's not perfect, and it's painful! Right, exactly. 

But now, on Tik Tok, people are like, "my child just cleared this table off. And now I have to clean it up." Or they're like, "breastfeeding fucking sucks." And, yes, it does!

So, anybody thinking about becoming a mom now has much more information than before if they're looking for it. And some people are actively seeking that out and making a conscious choice about it. Some people still have blinders and want what they want for whatever reason. But somebody's made the blinders choice first.

Consciously, I think about my own mental health and like what I have to spare. [Parenthood] is a very "if you do it for the right reasons," it can be one of the most unselfish acts you can contribute to the world. But it can also be extremely selfish if you're not thinking about it clearly. 

As far as being a writer, writing was always something that I always wanted. But it was something I didn't really have much control over. It was happening, like whether I wanted to or not; I didn't make a conscious choice.

A great illustration of this was when I was in first grade, about six or seven [years old]. We were learning cursive. I already knew how to write cursive because my mom had gotten me one of those books to learn earlier. And so, when we were learning cursive in school, I was a bit bored. So when we got the blank notebook with the three lines to practice, I already knew how to do it. So instead, I just wrote a story. It was like a book because I filled the whole notebook. It was about a little girl who found a magic ring on her way to school and about the adventures she'd go on. My mom probably still has this story somewhere.

My mom was always ahead of the curve when it came to that stuff. I knew how to read before I started school. She was just on it, and she was super involved. And that contributed a lot, too [to becoming a writer].

I also remember we went to Disney World when I was eight or nine. We'd get this little autograph book where you're supposed to go to the characters, and they have a little stamp, so it's like getting Mickey Mouse's autograph. So I got two autographs and then [used the book] to write eight-year-old poems.

So any time you had a physical pen and paper? Right, it's going to come out. I was still young, but I don't remember what was going on in my head. It just happened. As I got older, I made a more conscious decision to be like, "oh, I want to write a poem, or I have an idea for a story or whatever." I was just somebody who always had stories and words inside of me. 

Were other factors or people encouraging you to write, or were you interested in it yourself? My parents gave me a lot of positive reinforcement, for sure. I wrote a story, and they read it. They'll be like, "oh my god, this is great," or whatever. I figured that based on your initial story of how your mom is likely to have kept your first story! Exactly. And so, I definitely got positive reinforcement for doing it.

I was also a little people pleaser. I was a little good girl or whatever. And so, that probably did encourage me to know that people would positively react to me. But I wasn't looking for that the first few times I did it. It was a byproduct. Even now, when I try to take a break, I get ideas for things. And so, I think it's unconscious.

Making a conscious choice to pursue [writing] as a career was definitely really scary. The self-doubt was totally a part of it. And it's still there, even with published books.

So did you get into publishing right away? Could you share how you got started? In college, I knew I wanted to be a writer. But I was too afraid to say that out loud. And so, I started looking for other things that I was interested in and good at. 

It came down to two things. I love books and words, so publishing [was a path]. And I love kids, so that was teaching. I did some teaching internships and worked at daycare centers, the YMCA near my college, and all that kind of stuff. Teaching just felt like a much more accessible goal at the time.

And so, when I graduated, I got a teaching job. I was working at a Montessori school with infants and toddlers. Montessori schools are all about fostering independence in very young children and essentially child-led learning. 

To advance [in the teaching career], you need to go back to school to get different certifications to work at different schools to move up. Additionally, for me, there was so much red tape. For the administration stuff, just having to do things because you have to or because some established process existed and you just had to do it [didn't make sense].

Parents are also fucking nuts. As a parent, I can say we're crazy! laughing And it just wasn't what I wanted or expected it to be. It was mostly dealing with administration. The parents—I could handle. For somebody like me who deeply loves children, it was very frustrating whenever I encountered a parent doing something harmful to their child and never on purpose. 

Parents advocating for their children was totally fine for me, as I could deal with that. But when I saw active harm, it was very stressful for me. I was worried I would get into trouble because I was like, I'm going to say something I can't. So that was part of the reason why I was like, "I cannot do this long term." 

Those are the two reasons why I felt that [teaching] wasn't sustainable for me. So while working that first teaching job, I started reading this book, "I'm an English Major, now what?" It had all of these career paths that you could take.

One [path] was these post-grad publishing programs. They're six-eight week intensive programs where you learn about the publishing industry. At the end of it, there is a career fair. The idea is that you'll go through the program and find a job.

I loved the program. The first three weeks were about magazines, then the remaining was about books. I went into the program thinking I would get into magazines because I subscribed to 80 different magazines when I was a teenager. And I really liked the idea of going into advertising or doing editorial stuff for magazines. I also liked the glamor of it. But, when I was going to the program, the people were fucking terrible. So I was like, "Okay, these are not my people." Then the books part of the program came. During that, I was like, "Oh wait, this is actually what I want to do." 

As part of the program, you had group projects to make a magazine and an imprint. You had to come up with a list of books that you were publishing. It's very cute and actually gave you a lot of information about how it all works. 

Unfortunately, in the end, I did not get a job right away since I did this program in 2009. I had no money, so I couldn't stay in the city. So I went home to D.C. and applied for jobs in the area. I ended up doing a couple of internships where I was a personal assistant for an author, another working at a magazine, and another where I was putting together a college guide. The internships were very publishing adjacent but not actual publishing jobs. laughing I haven't thought about these internships in forever!

And so, what happened after these internships? During 2010, I started applying for publishing jobs in New York because I was like, "I gotta get the fuck out of here." Like, this was not sustainable. So, I used [my then boyfriend, now husband] Cass' New Jersey address to apply for roles. Then, I would take the Amtrak up with my dad in the mornings to go to interviews, have lunch, and head back home afterward.

And eventually, I got a Marketing Assistant job at Random House. While I was there, I was writing the whole time. But I also wrote a book that was garbage. So I needed to learn how to edit; I didn't have a writing community at the time and didn't know anything about revision. 

At the same time, I'm getting acclimated to my new job and like all that stuff. And I started reading some of these books we were publishing, and I was like, "this is shit!" I have some of those moments in the design world as well! Right. It's like, if they can do that, why have I doubted myself so much? 

Exactly. And then, I started meeting people and learning about the publishing process. The way it works is that when you're first starting out trying to get published, it's best to write a full manuscript before you start looking for an agent. Then, when you find your literary agent, they are your representative to take you to different publishing houses or to present your work to various editors. 

And once I learned that process, I started making a list of literary agents. You want to find literary agents who represent what you're writing or similar projects to which you are writing. So they know how to pitch you? Exactly. And agents are known for that. Agents also tend to represent authors who are writing things that they like. 

To find an agent, you need to query them. And the way querying works is that literary agents have on their website the way they prefer to receive manuscripts. So, for example, some literary agents want you to send them a letter, so you write a "Query Letter." It's basically like, "Hi, my name is this. This is what my book is about." And you'll have a blurb of your book, share any accolades you have, like where you've been published. You then share that this would be, for example, "my debut work of fiction" or whatever it is that you're currently doing. Ah, this sounds like a cover letter! Yes, it's like a cover letter for your book. And so, it's really important to have a strong one.

Some literary agents want the letter, and some want the letter and the first five pages. Some agents want the letter and the first three chapters. And so, you'll send your query letter out based on their specific criteria, whatever they are. 

Then, you'll basically wait to hear back. You send it out to the ether, and then what could happen next is that you'll never hear back again, get a rejection, or you get a request for a full. If they request a full, that means they liked what you sent and want to read the rest—which is very exciting when it happens. But at the end of that, you could still get rejected? Yeah.

And how did the first book you queried go? When I first started, finding a literary agent also took forever. I actually queried the first manuscript that I was writing. But again, I didn't know jack shit about revisions or how to cut things. And so, I queried the manuscript for like 18 months. I got a few requests for fulls and no offers of representation. So after the eighteenth month, I was like, "maybe we're done here." So I put that aside and started writing something else. 

Around that time, I was working at Random House in Marketing on adult books, and I really wanted to get into Kid's books. Because, again, my interests were the same the whole time: I like books, writing, and kids. So I really wanted to get into Kid's books. And so I applied for a position in Children's books, and I got it. It was super exciting.

I loved my boss when I was working on the adult side. And I was actually nervous about leaving because it's so unpredictable, and I needed a healthy work environment to write. Which is also very rare! Exactly. It's very hard to find, and I knew that I was lucky that I liked my boss. I felt like a valued member of the team. But I didn't realize how lucky I was until I went over to the Children's book role, and it was a fucking nightmare. I cried every day—it was awful. I was so sad. After nine months of being there, I was like, "I have to get out of here." And so I started applying for new jobs.

I said to myself, "I won't, and I don't even want to stay in publishing." So at this point, I just needed to get out because it was terrible. And I got a job with McMillan with a lovely person. So I was back in a healthy work environment. 

Once I started working at MacMillan, I started writing again. I finished the book, [The Beauty That Remains], within six months. And I queried this book for three months before I got an offer of representation. It was super fast.

When I first started writing that book, I felt like it was special. It was the right kind of thing. So many things were happening simultaneously, reflected in the novel about grief and anxiety.

While I was working that [initial] terrible job, my grandmother passed away. A lot of my abandonment issues were flaring. I started having panic attacks because I thought it wasn't a good place to be when I was in that terrible job. This was also the time that Cass moved to San Francisco. I was terrified that something was going to happen to him, and I wasn't going to know. 

So that book came from that particular time. The offers of representation were so quick. When I picked my agent, amongst the four who responded, the book went to auction, and multiple publishing houses wanted it. And it was a very exciting first experience.

What do you think made people grasp the book so quickly? Well, it was the third or fourth thing that I had written all the way through. I was getting better at knowing how to make a book. It was the first thing that I wrote that was extremely personal that came through in the text. I was writing for my younger self and my current self. I was telling myself that it's okay to be scared and to have all these feelings about things and that, ultimately, you'll be fine. And so, that is what resonated. I also think people fucking love sad books, but it's also hopeful.

The book also offered different perspectives to help reframe and think about how everyone has their own point of view. So all of those things came together to make it work. The timing of it was also good because that year, Contemporary YA (Young Adult) was having a resurgence. But also, so much of this shit is up to luck and timing. But you were also prepared. Right. So you can be as prepared as possible and just hope that your book happens at the right moment. I got lucky that it did! laughing And I continue to get lucky! You also continued to put in the work! For sure. 

And then, once you have an agent, it's much easier to have your foot in the door and additional deals after that, as long as you continue working. I love that your life has recurring themes in the joy of writing and interest in kids—personally and professionally. You were initially figuring it out and now intentionally putting so much work into making writing as a full-time career. And, of course, you have multiple careers throughout your life as a mom, writer, and so much more.

Why does the work you're doing matter to you? Or, in other words, why does it matter to you to focus on these particular values? I have always had a soft spot in my heart for children. I've always known at a very young age that I would be involved in kids' lives in some way. Because teaching didn't really work out or because I couldn't deal with the trauma of it. I knew that I still wanted to feel like I was having some kind of impact on kids. And like learning to heal your inner child: helping or feeling like I'm helping other kids helps younger me too. 

There's also the representation part of it. There are so many kids who don't have an opportunity to see themselves in books. And so, if I can write a book that helps a kid who never saw themselves before and see themselves beyond "this character is Black" or "this character is Asian" but actually on an emotional level too–that is what I want to do for the rest of my life. 

I want to make sure that people feel seen and feel like their existence matters. Life is hard, and if I can do something that I enjoy doing and it makes somebody's life slightly less hard, that is all I want.

I want to make sure that people feel seen and feel like their existence matters. Life is hard, and if I can do something that I enjoy doing and it makes somebody's life slightly less hard, that is all I want.

Are there any misconceptions about yourself, your identity, or your work? YA [Young Adult] has a bad rap. People think writing YA is easy, writing books is easy, or writing books for kids is easy. 

People also think that everybody in publishing is making millions of dollars all the time. Maybe the publishing company? Right, but sometimes not even the company. 

People think you're set for life once you write one book. Or once you write one book, you're guaranteed to write another. But I know many people who only wrote one book and never wrote again. 

And so if you want to make it into a career, it requires a lot of commitment, work, and tenacity. So many people I know who are career writers have another job. I am very lucky that I am able to write full-time. I know a lot of people who are not able to do that. That's a combination of me having gotten very lucrative deals—which is great. And also have a supportive partner who has a great job and is open to me not having a full-time job because, living in New York City, it never hurts to have more money.

[Writing] is less lucrative than people think because the splashiest deals or the ones that reach beyond the inner publishing circles are the hugest. So people who are not within publishing, the deals they hear about are the ones that are big, get movies, and are best sellers. But unfortunately, that is not the case for the majority of humans who write books.

And the whole "kids' books are easier"—kids' books are a lot harder than writing for adults. Adult books can be as long as you want them to be. Kids' books can't be super long. Picture books are also really hard. 

People are used to reading the finished product and never see the process. They never see the process like most books you're reading has gone through three or more edits of the entire thing like they have been rewritten from scratch. 

There are so many misconceptions; we can talk about misconceptions all day!

Reflecting back on your career, do you have any self-doubt? A very good example of this is that I published a book this year called, "Nothing Burns as Bright As You." It was my first verse novel, so the whole thing is written poetry. And it's gay, and it's about two Black girls. So everything about that had me shitting my pants.

It wasn't that anybody knew that I was writing it since we were in a pandemic. It was a book that came out of me through complete isolation and not having to worry about external expectations. And through therapy and processing a lot of shit that had happened to me as a kid and things that were happening to me at that moment. And just like all these feelings, I had never truly taken a moment to process them. So, it was an extremely vulnerable book.

I was supposed to be writing a different book. And so, everything about it was terrifying. When I sent the book to my agent, she read it and said, "this is great." It also felt like, in my gut, it was the best thing I had ever written. But I was terrified it wasn't the best thing I had written, you know?

Terrified because other people would think it wasn't the best thing you wrote or that you thought that about yourself? Because I wrote it in such a vulnerable place, I was afraid that everyone would read it, which would color my feelings about it. The more revealing something is, the less I'm able to divorce the reception from it. It was also a hidden part of me that I had never really processed or even thought much about my queerness until a year before the pandemic. I had an identity crisis, and then we got stuck at home.

[For context], once you get an agent and a lot of agents are editorial agents, you might revise with the editor or agent before you go out to editors. And when that agent sends your book out to editors, they're essentially sending another query letter to editors to say, "hey, this is my client's book, and this is what it's about." [This process] is called "going on submission." So it's a very similar process where you're just waiting to hear back. 

And so, when I went on submission [for Nothing Burns as Bright as You], it was only four days which is incredibly fast. But every day I was on submission, I vomited. Every. Single. Day. I didn't put anything down because I was so anxious. 

It was awful. I was afraid that people are going to say that I'm not gay enough to write this book because I have a male partner. People are not going to care because it's too black. And you don't see many sapphic stories generally, especially not with black girls. The book is in verse, and it's fucking weird. It's a weird ass book! It's just feelings everywhere.

And so, I was just so terrified. It's probably the most recent experience I've had with self-doubt. It was just like...I shouldn't be writing this book. That is how I felt a lot of the time I was writing it, promoting it, and talking about it.

It's such an interesting insight because earlier, you shared that after getting your first book published, we would assume that it should be smooth sailing and that you'd be more confident. But, no! Each time you go through it again, it's just a different level. 

And what I find really interesting is that your first book, "The Beauty that Remains," came from a place where you were processing that became a reflection of that particular time. Ideas can come from a place of being vulnerable, which is such a beautiful reminder that self-doubt will come out, and it's more important what you do with it and moving forward.

The important thing about any creative work is to be a little bit relentless with yourself but also with the outer world. The way your work is received is not so much a reflection of you but more of a reflection of the time and space the other person is in. There are so many different things that come into play. So, it's not always about you, even though it feels like it is. Something I'm currently learning as well.

The way your work is received is not so much a reflection of you but more of a reflection of the time and space the other person is in... So, it's not always about you, even though it feels like it is.

There's this video by Ira Glass where he's talking about creative people and their tastes. He's saying that if you're a creative person and if you're a person who likes to make things, then you have really great taste. But when you first start making things, whatever you make will not live up to your taste. The only way to get better is to keep making things. I always think about that because when I think "this is bad," it's because I have good taste, and I haven't had a chance to make this good yet. So I think about that a lot, too, especially when I'm in the first draft stage where everything fucking sucks! laughing

Every book is different; for instance, "Nothing Burns as Bright as You," I did very little editing to it. But everything I've worked on after that has been more normal, where when I write something, I have to edit it again and again and again. You'll never know; another book could just come pouring out again! Exactly, you'll never know because every book is so different.

What would you say if you could pick an Ashley in the past and give yourself advice? Jesus, there are so many different ones! 

If I could talk to my 15-year-old self, I'd be like, "Just kiss a girl. Just do it now and get it out of your system!" So that we know that "that feeling" is valid. And that, you can like girls.

From a creative perspective, I would tell the Ashley querying the 18-month-long novel that, "that is not the story, but that doesn't mean you won't find the story. And it's okay to let it go. Like, you can stop." But I also think part of that process really prepared me for the next thing, so I'm not sure I would change that experience. But, I would be open to telling my younger self that "you can write something new."

I would tell my 20-something-year-old self who wanted a baby, "no, you're not ready." And to "take your time, focus on getting to know yourself better because that will make you a better parent in the long run." I obviously didn't have a kid then, thank god! But I was in such a rush. It was because I didn't want to deal with not knowing what else to do. [Having a baby] was something I always knew for sure, and I didn't want to take the time to actually get to know what else I wanted to do aside from being a mom. So, I think it would have been a mistake to have a kid at that point in my life without figuring out myself a little bit more.

And what about now? What do you currently have on your mind, present day? It's important to think about what you care about more than anything else to find your voice. And then use that to guide a lot of your decision-making. I didn't start doing that until very recently, and I wish I had done that earlier.

Even if you're not consciously making that choice, the things you care about will tend to float to the top. Your life can feel a lot more focused and a lot less directionless if you make those decisions and then use that information to guide the decision-making. 

For instance, the fact that children have always been important [for me]: I think I should have kept this in mind when I was first applying for publishing jobs and only applied to work with kids because that would have made my life or my path a lot clearer and straighter. 

And thinking about representation—I did think about, for instance, when I was applying for agents. I was not thinking about representation for the first time [applying]. But the second time, I was like, "you know what, I really want to work with a person of color." So when I was much more focused the second time, I made a list of agents and picked only women of color; I got an agent. I actually got four agents interested because they recognized something in my work that was important to them—the representation of kids of color in the book. 

Taking the time to think about what is more important than anything else would make your life so much better and make your path straighter. That goes for finding your voice as well. Because once you figure out what's most important to you, you know how to dedicate your time, use your voice, and do what you need to do. It provides more clarity and direction that you could take. And not that you should take it, but you could.

Taking the time to think about what is more important than anything else would make your life so much better and make your path straighter.

Right and recognize your strengths, even if the world doesn't see those strengths. For me, I've always been extremely sensitive and extremely feelings forward. For a long time, I saw that as a weakness because the world doesn't really value that in the same way that I do. But recognizing that as a strength instead of a weakness has made my writing so much better. Because I now know how to pull on those heartstrings. I know how to make someone feel seen. And I realize that that is where my voice is strongest. And that's okay.

I'm not a big plot person. Plot is great! But that's something that I have to actively work with. But feelings, those emotions, like that is really, really easy for me, and it comes very naturally to me. And so, recognizing [your strengths] and then building your brand around what you're best at will make your voice and your contribution to the world stronger because it's based on something already there.

And so, recognizing [your strengths] and then building your brand around what you're best at will make your voice and your contribution to the world stronger because it's based on something already there.

Give us a list of 3 things you'd recommend.

These are my must-haves to have a comfy experience while working. My work is writing, but this can be relevant to anybody doing any sit-down work.

1. Sony WH000XM5 headphones. I remember the exact model name because I did so much research on these! They are one of the most comfortable headphones I've ever had. The sound quality is amazing, and I can wear them for hours without being uncomfortable. They also keep my ears warm, so I don't need to wear a hat. They are also Bluetooth, so they can connect to your phone or laptop.

2. Free People Socks. I love all the socks from them because they make really thick, soft socks. They're so cozy, and cozy is very important to me.

3. Matcha Latte Powder from Trader Joe's. I love it. The instructions on the back say to use three tablespoons of powder with hot water. But, what I do instead is take oat milk, heat it up, then add only two scoops, and the powder last so much longer. It's so fucking good. You could also just put it in a mason jar and shake it up.

What song do you currently have on repeat?

Swan Upon Leda by Hozier. This one is sad and very much a rainy-day song. It conjures feelings like you're in the woods with a cozy, maybe fireplace situation.

Drive and Disconnect by NAO

Enjoyed the Conversation with Ashley Woodfolk? Learn more about Ashley at www.ashleywoodfolk.com. You can also find her on Instagram @ashwrites and Twitter @ashwrites.

Ashley is also passionate about giving back to Food Bank for New York City. As part of this Conversation, a donation was made to Food Bank for New York City.

You can support Food Bank of NYC by donating directly.

Donate to Food Bank for New York City

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Meet Faraz Ahmad, a father, husband, brother, and a Senior Software Engineer at Netflix. He shares with us how his north star of providing for his family has guided him throughout his life and career to find safety and stability through resilience and a deep desire to learn. We talk about his childhood, the paths he chose, some stumbles along the way, and ultimately how full circle many of his decisions have been in hindsight.

Interviewed in October 2022

Heads up, the interview contains some explicit language that may not be suitable for all audiences. Interviewed in December 2022.

Tell us about yourself. My name I'm Faraz Ahmad. I'm a Senior Software Engineer at Netflix. I'm in New York City. I'm married and have a kid. I'm originally from Orange County in Southern California and am happy to hang out and talk with you.

Happy to chat with you as well. Let's go back in time and share a bit about the start of how you got to where you are today. My family is Indian. My dad and mom are from Hyderabad, South Central India. My dad moved to Toronto in the 70s, and he was a mechanical engineer at the time. After Toronto, he worked in Detroit, Michigan, and made cars on the car lines at General Motors. While working there, he noticed a shift in the early 80s when computers were becoming a thing. So he went back to get his Master's [degree] in Computer Engineering. That led him through a different career path and moved him to California. Since then, he's been doing Systems Engineering work.

Being surrounded by tech definitely played a big influence on my life. My dad worked in tech and has worked remotely since the early 90s. So, I remember him being around all the time, which was nice. I also have an older sister, the first daughter of our Asian immigrant family, who followed the mold. Both my dad and my sister both went to school for Computer Engineering.

I remember very distinctly, right out of college, my sister got a job as a Software Engineer, and she bought a Lexus. And, I was like, "Oh my god—this is peak luxury." It was crazy that my sister, who used to hang out with me, was driving this car. And to me, as a kid, I was like, "this is probably what I want to do" because, from a financial standpoint, this is going to provide me with the thing that I want to do with my life. So, this is where my interest in engineering started. So yeah, I went to community college and university to study Computer Science.

You often see what is in your peripheral vision, especially as a child of immigrants. So many folks, like myself, often think, "this is my only path." Was that true for you, that studying and having a career in engineering was the path to go down? That's a good question. Actually, for a long time, I was fighting [going into engineering]. I was almost like, "oh, I don't want to do this because my dad and my sister did it." I wanted to do something more creative. 

I was really into filmmaking in high school and college. Growing up in Southern California, I was close to L.A.—so I wanted to go into the film industry and become a writer or director. So, I originally started studying film. But then I got to my second year at college and realized none of my friends that were graduating were getting jobs. That was a big red flag, especially coming from my background. Not being able to provide for myself or help my parents financially was a really big scary thing.

So I had to think about what am I good at? What do I like to do? What do I have a familiarity with, and can I have support? A lot tied into "Okay, so I like the internet and actually using the computer a lot." I've always been building stuff and having my dad's influence with having a computer in the house and him being in the industry.

I've also seen firsthand the kind of life I could provide for myself and my family. So, this is pretty solid, and it feels safe. But, honestly, all of the unknown scared me. So I decided—okay, I will do this Computer Science thing. While I'm not super in love with it, I know enough that I'm good. I know my dad might be able to help me get a job, and my sister works in the field. 

And even if I'm not the greatest at it, I will have a decent life. I will have a steady paycheck and provide for my family and myself. And all of these things trump everything else.

You mentioned the word "safe." Why did that matter so deeply to you—to have that sense of security while growing up? My parents split up when I was really young; I was five. After we split up and lived with my mom and my dad separately, it was a very different environment between the two houses.

I saw a big difference between my dad and my mom. My dad was an engineer, and my mom was a teacher and homemaker. My dad was middle class and was solid in his career. My mom struggled to make ends meet. We lived on welfare and child support, and money was not abundant at my mom's house.

I started working at random jobs early in high school to help make the bills. I felt I was responsible for taking care of my family and had a need for security. It's a common thing for many people, and it's real. It's expensive to live here in America, and not everyone comes from backgrounds where when you're a kid, you can be a kid.

And so my main driving factor was seeing my mom struggle. I wanted to be able to provide for her and make sure she feels okay. At the same time, there are things I want to do. I didn't know the answer to any of the problems we had growing up other than that we just didn't have enough money. And so, I was like, "I need to make more right now...how can I do that?" 

It's cliché, but the way to do that was to get an education and a job that pays you well enough to take care of your family. My first realization was when I was in high school, where I realized I needed a plan for my life because I could see both sides of what my dad went through and the kind of life he was living compared to the complete opposite with my mom. At that time, I had to ask myself, "which of these paths do I want for myself and my family?" My answer was to provide stability and safety for myself and my family.

What was the experience of fully committing to the beginning of pursuing a career in engineering? It was really challenging at first because it was accepting that I was basically putting a pause on this dream for what felt like the greater good—which is fine. But, at the end of the day, do I regret this decision? No. I would do it again, 1000 times, because if you told me, I had to choose between my dream career or taking care of my family? I would 100% choose my family every single time.

Once you made that step, what was your life like at this point? What were parts of this new identity you're now embracing? That's a great way to say that it's a “new identity.” At that time, even though I was technically in my third year of college, I started over again because I had changed majors. So I had to reset to be a "freshman" again. I also had a lot of imposter syndrome. I thought about whether this path was for me. On the flip side, it was also nice to spend time with people younger than me because it was healing from the childhood I had missed because I was working all the time to support my family. I got to be a kid again with these other kids.

At the end of the day, I realized it was all a very early lesson about what being resilient was. Shit happens all the time in life and at work. And, like, what are you going to do? You can pout about it, or you'll move forward and pick up the pieces to try and make the best of the scenario. So it was all a big shock for me that this change was happening. But, it was also lucky that it happened early for me because some people aren't lucky enough to experience the realization of a need for change. After all, everything "goes according to plan" till after college and you're deeper in your career. And then shit just happens, and you wouldn't know what to do or how to react. Or you're suddenly 40 or 50 and have a complete crisis about your entire identity! It could be anything. So I'm grateful. In hindsight, I've had many of these challenges early on. It's put a lot of perspective into my life and has given me a lot of wisdom.

Shit happens all the time in life and at work. And, like, what are you going to do? You can pout about it, or you'll move forward and pick up the pieces to try and make the best of the scenario. So it was all a big shock for me that this change was happening. But, it was also lucky that it happened early for me because some people aren't lucky enough to experience the realization of a need for change.

Switching to engineering itself isn't easy. It's not an easy subject, and I find Computer Science hard. I also wasn't a great student. A lot of it was because I wasn't also a student—I was working full-time simultaneously. I was doing whatever I could to get by and graduate all this time while trying not to get kicked out of school—which almost happened to me several times. There was no way I was going to let myself fail or quit.

So I finished college at around 25-years-old. Then, I started applying to hella jobs. The job I got right out of college at IBM is a full-circle moment because my dad's first job was at IBM when he moved out to California. You could say it was divine or meant to be, the only problem was that it was in Ohio. So about 90% full-circle moment!

But, I wasn't thrilled. No shade to Ohio! Laughing Growing up in Southern California and then having to move to Ohio... I wasn't super jazzed about it. But I was very proud that I fucking landed this job. They were going to pay me well, maybe around $70K at that time, which was the most money I'd seen in my entire life. Ohio is much more affordable than California, so I could move there, get a really nice apartment, and still be able to send money home.

But then a wrench got thrown into it. I met my now-wife as I was getting ready to move. And I was, like, "oh shit, I really like her." I didn't want to move to Ohio because I wanted to see this relationship with her through. You know, so life happens, right?

Again, family is always my North Star. And, like most people, they want to meet somebody and be in a relationship. So, when I met her, I decided that it would be okay and that I should try to find a job here [in California] instead. So, I kept applying even though I had this job lined up in Ohio.

Ironically, though, I ended up at a tech recruiting fair and a family friend who knew my dad recognized me. So, I gave it a shot and decided to interview with a health-tech company called Optum from the fair. And that is definitely a privilege where I was lucky that my dad had already built these relationships that allowed me to get in the door. Otherwise, that conversation [at the recruiting fair] would have never happened. The position was for new grads in Southern California and paid more. So, I could continue to date my now wife and can stay home to continue supporting my family. 

So when I joined this company, it was fine. I didn't really know what I was doing. In the first year, in any job, you don't have a lot of mentors, so it was very challenging [for me]. The company wasn't really great at mentoring either: it was like they decided to just bring on a bunch of new grads and put them in a room and see what happens. It was hard, but it was fun and felt like college again, except we now all had some money. I had a similar experience with my first role as well! One of the benefits of going into a new job with a group of people is that I ended up with some of my close friends. Yeah, it's a lot of just trying to figure stuff out together. 

I really struggled my first couple of years in my career because of this internal battle where I didn't find a love for my craft until a couple of years later. But I wanted to make the most of it and be happy since I was getting paid well. I also had some poor management experiences and ended up jumping around jobs. 

Fast forward, I decided to join a startup which was a big turning point in my career. At this time, I was pretty scared. I had been working my whole life to build stability and security for myself and my family...and then I decided to become the first employee for this startup where it was just the founder and me. It was also the cool thing to do in 2015 when everyone said, "you should go work at a startup in New York."

I thought I could learn a lot more because I wasn't learning a lot at the healthcare company. So I figured I would be a lot more hands-on, code more, and learn more about product. It was very challenging, early, and chaotic. I bumped heads with the founder. We're friends now and we're cool, but at the time, I was very young and stressed out about the company. 

Afterward, I kind of bounced around. I worked at a couple of other startups and was lost. I was wondering if this career would work out for me and was really scared.

On the one hand, you craved safety and stability, but you left that for the opposite...where chaos could lead to more potential growth in your career. At this point in your journey, did you realize that you wanted to make peace with yourself, the journey, or the choices you were making, if at all? That's a really good insight. And I'm glad we're talking about this since we don't usually talk about stuff like this. At that time, I had not made peace. I would say I was in the deep end, where I was really confused. I had a lot of imposter syndrome and didn't know whether I would make it.

It wasn't until I got this job at a startup called AdHawk that I met my old manager, Ian, who took a chance on me because I was very unproven at that time. Up until that point, I had basically changed jobs every six to seven months because I couldn't figure things out. Or these were the wrong positions that didn't allow you the growth or support you needed to grow in the way you wanted.

Right, and so I think Ian was my first true mentor. We had similar backgrounds and life experiences. He said he saw something in me and thought, "okay, there's something here that we could figure out." He really grounded me because he provided a stable growth plan. He allowed me to learn and gave me opportunities to grow.

I felt safe again because I was allowed to make mistakes, learn, and ask questions. It also helped me realize that it really matters who you work for, like your boss and your supporting group, which makes a huge difference. They made a very safe space for me to explore what I wanted to get into and figure out what I wanted to specialize in.

And it wasn't that the startup was chaotic, but it was like we were all in it together. We had a group of 10 engineers and figured it out as we went. Everyone was also roughly my same age and we're all in New York, so it was just fun. At this point, I also realized if this is what working in this space [in engineering] could be like, then I would love to work like this. Because it was really creative and fun. 

So what happened after AdHawk? Did you continue to pursue engineering more openly? Yeah, after two years at AdHawk, I decided to specialize in web and front-end engineering. It feels more creative. I work with designers and talk to users. It was fun; I've always had this itch to be creative. In a sense, it was like I got to paint on the browser canvas. It satisfies me enough to where I enjoy coming to work.

I initially wasn't considering leaving AdHawk when [the opportunity] at Uber came up. But, at the same time, I was scared because I felt like I finally found this place [at AdHawk] where I was really happy. 

But then, going back to the north star of my family, at this time, I'm married. My partner was expecting our first kid, and I had to take a step back to ask myself, "Do I feel safe and feel confident?" And I did. I made peace with this career choice where I felt like I belonged and could do this. 

So, I decided to take this interview at Uber. I was considering two main things: is it going to pay me more, and am I going to be able to learn more? And I felt that I could do both, so I took the job at Uber and was there for two years.

With any new job, you're learning a similar cycle. At this point, I felt that I had the tools and was better equipped [to take on a new role]. And I now have a blueprint of what I need to do to succeed at a company or any company based on everything I've experienced. Through all this, I felt resilient.

I got more passionate about my work because the end result was that I got to provide for my family. To me, that's my motivating factor. But, again, I mentioned earlier that I'm not one of those people who loves Computer Science or computers or programming. It's a means to an end. The end is providing for my family. And so long as I have that north star and Computer Science allows me to do that with a relatively comfortable lifestyle and where I'm not working crazy hours.

Some people have different motivations. Some are really motivated by work. In my case, I'm motivated by my family. It doesn't make anyone less of an engineer or less of whatever they are in their careers. It's more about whether or not you can show up, do a good job, be friendly, and build the things that matter the most.

“Some people have different motivations. Some are really motivated by work. In my case, I'm motivated by my family. It doesn't make anyone less of an engineer or less of whatever they are in their careers. It's more about whether or not you can show up, do a good job, be friendly, and build the things that matter the most.”

Often, we hear that people's lives revolve around their careers. And to be successful, you have to be successful at your job. What do you believe in? I see this discourse a lot. It's probably Twitter drama, honestly. But it's like if you're not living, breathing code all the time, then you're not going to be a successful engineer—and to me, that's a misconception. I don't know what they call it; maybe "Hustle porn," where you must be coding all the time, day and night. You have to be doing side projects. And where if you're not trying to start your own company, you're not a real engineer blah blah blah. It's always this gatekeeping nonsense.

I don't understand what it is. My perspective is that people obviously want better for themselves. And maybe that's how it's been portrayed to them. So they assume from the outside that this is how people look. I'm not saying it's the wrong way. I'm saying there are multiple ways to look at it. 

There are probably people like me who are not crazy about engineering. I want to provide for my family, and I like doing it. I'm okay. I'm pretty solid and decently good at it. But I don't live and breathe code. I don't think about it after I close my laptop. I have a regular life and want to live my life.

And I think that's also really important to call out: “why are you doing this?” In the end, I don't want to be 50, look back and be like, "what did I do with all my free time? Did I spend time with my family, or did I talk to my friends? Did I call them on the phone? Did I get to go eat hotpot with Leslie?” Did I stare at a laptop all day and night, and that's it?

Right, it's okay to unplug! Honestly, I would argue it's better to unplug because it gives you more perspective on your career. It'll help you better understand why it's important to you. You'll get to meet people you wouldn't really talk to to get out of your normal circles. The world is so big, and many interesting people are out there. I just find that you don't have to be plugged in all the time. Go live your life, and you'll feel more balanced. You'll feel more whole. Yeah! Because your career is just one part of your life.

The world is so big, and many interesting people are out there. I just find that you don't have to be plugged in all the time. Go live your life, and you'll feel more balanced.

Maybe some people go into their jobs with the mindset that "this is my career and what I really want to do." And it's fine to go down that trajectory. But, for me, it was not like that. It was simply, "I just need to do this," and that's totally fine. Both are valid. It's all valid. But there's room for people to understand that it's not one-and-done. 

One last thing I want to share is that I always get emotional thinking about it. I'm super blessed and happy to work at Netflix now. My dream came true differently because I always wanted to work in film. And now, in just a different way, I am. And I'm doing it in a way that I'm able to provide for my family.

That's so real, though. It was hard to get to this point in your life, but being able to do that and find success—however you want to define it—matters. A lot of what you experienced early on in your life, from the burden we carry as children of immigrants, could be seen as negative. But, to me, it's also a big positive because it gave us the fuel to get to where we are today. The present doesn't exist without events and the decisions we've made in our past. Exactly. I always tell my friends that [this current job] is my dream job. If you were to ask me as a kid if I thought this was where I would be, I couldn't imagine it.

Another full-circle-related question—what advice would you want to give the past you who just started the beginning of your journey to get to your dream today? For Faraz who was choosing a path between film or engineering and who was asking the questions of "Am I making the right decision? Am I going to give up on my hopes and dreams for my family?"—I would say that these questions are valid. And knowing what I know now, I would tell myself, that “yeah, dude, you’re doing the right thing and making the right decisions.”

And things will work out. And if it doesn't, [I'd tell myself] that I'd be fine, and I'll figure it out.

I would now only believe this after my experience of working at AdHawk and having a mentor who would remind me, "you're doing the right thing, and you're going to be okay." Because once I accepted [that advice], and when I made peace with the idea of safety, it became a full circle moment. It helped me realize that it's not always going to be safe. It might be chaotic, but I'm still resilient.

That's beautiful. And being able to reflect on such a crucial time in your life to find that you're still on track for what you want. 

Yeah, it's really nice to sit back and reflect because we get stuck in our day-to-day lives. This [conversation] was a good reminder that I can tell my younger self, "you've come really fucking far!" Let's celebrate that.

Celebrate that and take time to be grateful. And show gratitude and be really proud of yourself because you've come a long way. You've learned a lot, and you'll figure it out. Laughing Now, I feel like a wise old Indian dad! Well, you are a dad! Laughing I am a wise old Indian dad.  

But yes, you're right. Everyone's journey is different. So I hope people who are feeling like their life is a bit chaotic right now, or doubting themselves, [can be reminded] that it's going to be alright. There's a path forward, and you'll figure it out. And it's not the end of the world. And to stay resilient by being grounded.

Everyone's journey is different. So I hope people who are feeling like their life is a bit chaotic right now, or doubting themselves, [can be reminded] that it's going to be alright. There's a path forward, and you'll figure it out. And it's not the end of the world. And to stay resilient by being grounded.

What song do you currently have on repeat?

In all honesty, I listen to whatever lo-fi playlist is on Spotify. Here's one I've been listening to. Otherwise, my number one song on repeat is Baby Shark, obviously because of my kid!

Give us a list of 3 things you'd recommend.

Friendly advice:

1.  Take a class on film making, it’ll forever change the way you “watch” movies

2. Do yoga every day it’s good for you

3.  Call your friends on the phone once a week 🙂

Enjoyed the Conversation with Faraz Ahmad? You can read Faraz’s substack for more musings online.

Faraz is also passionate about giving back to The International Rescue Committee (IRC). The IRC helps people affected by humanitarian crises—including the climate crisis—to survive, recover and rebuild their lives. Faraz believes in its mission to support refugees from different countries who are seeking a better life. As part of this Conversation, a donation was made to IRC.

Donate to the IRC

Meet Jing Jing Tan, a psychology geek currently leading user research as a UX Research Manager at Uber Eats based in Toronto, Canada. She shares her journey into studying psychology through Human Biology and the leaps of faith that helped her navigate her way into the tech startup world. Additionally, she breaks down how and when leveraging user research can give early signals during product development to help decision-makers focus on the right problems to solve, thus narrowing in on the right solutions and offering more efficiency in the overall process.

Interviewed in March 2022

This conversation has been edited for clarity and brevity.

Tell us a little bit about yourself. First and foremost, I am a psych geek. I love channeling psychology to be the bridge between the people using products and those making decisions about those users. That's what I've been working on for the past decade.

Growing up in a typical Asian household, I had two choices for a career:  being a doctor or an engineer. So I decided to pursue pre-med at university and enrolled in Human Biology. I volunteered at hospitals, started clubs, and got good grades. I was doing all the right things to become a doctor. Unfortunately, then a quarter-life crisis hit.

In my third year [of university], while volunteering and doing biology-related research, I had a breakdown realizing that it was not the path I wanted to continue. Which led to a soul-searching conversation with my mom because I knew she hoped for me to get into med. She ended up being supportive of what I wanted to do. Luckily, I was able to finish my Human Bio courses, added on Psychology at the end of my third year, and managed to graduate on time. I loved the additional year and a half I got to specialize in psychology.

Those courses opened up my perspective on my world views and how we behave in the world. Views included how we interact with each other, geographically and internationally and how there are differences in people's behaviors based on cultural upbringings. I loved every single second of it. 

After graduation, I was interested in the international element of interacting with people and applying the knowledge I learned. So I taught English in Korea for a bit and then did my Master's degree in Ed-tech. That was my first foray into Tech overall, which opened my eyes to how psychology can be applied in a tech startup environment. Since then, I've been working in Tech and stumbled into UX research by accident with the help of a mentor at the first tech company I worked at. And I loved it. That's what got me into this field. 

You mentioned that you initially only knew of two career paths: being a doctor or an engineer. How did that happen? Mostly because my mom was a doctor and my dad was an engineer [in China]. But, unfortunately, both had to give up their stable jobs to come [to Canada]. It breaks my heart to see really smart, qualified people like my parents having to start from zero. Their experience made me anxious about moving into psychology because there's little certainty about that path.

What was your experience of putting a stake on the ground and declaring, "I'm going to chart my path," instead of going for what was expected of you at that moment? It was not easy at all. I had a crisis while working in a research lab. I was mating worms and doing genetic experiments to see which genetic markers crossed over. One day, I walked into the lab, thinking the worms had died and I would have to start the experiment all over again, and I was like, "I'm so tired of working with dead worms!" So that day, I walked into the university's Counseling Center and broke down.

The front I was trying to put up with for myself and my parents was breaking down. Speaking with the counselor and bawling my eyes, I told her, "I don't know what I'm doing. I don't want to do this anymore." I was worried that I was wasting time. She reassured me that "what you learn is never a waste. The way you learn to break down problems, think about experiments, and how human biology ties into psychology and behavior is not a waste. Knowledge is buildable rather than being a waste."

So that was the reframe I went to my mom with as well. I was upfront and shared, "Mom, I'm not happy. I don't think I'm cut out to be a doctor. And here are some of the reasons..." She was torn initially because [being a doctor] is the only thing she knew about that would provide me a stable path. But over time, she realized that my happiness was more important than certainty and stability. And so, I was able not only to convince her but myself that it was the right path to move forward.

I remember feeling like a huge weight lifting off my shoulders after those conversations, and having her support meant a lot to me. I'm happy that we both took a leap of faith, and things are working out now because we would never have thought this job [user research] existed. 

Would you say that happiness contributed to your ability to find a future that could be more fruitful for you? Perhaps my mom thought stability leads to happiness. But I thought differently—that happiness could lead to stability. While you're doing things you enjoy, you will find ways to make it work. You will find that nowadays, people have different side hustles. People have much more freedom with what they decide to work on in life.

While you're doing things you enjoy, you will find ways to make it work. You will find that nowadays, people have different side hustles. People have much more freedom with what they decide to work on in life.

That mental shift was something that [my mom and I] ended up having. My mom is from an older generation, so she didn't have as many opportunities to build the life she envisioned. She had to choose a path and believed that it continues to be the path that brings happiness. But I think between her generation and ours, there's now a shift. There are more opportunities; there are a lot more ways where we can design our own lives. So I'm happy that she took a leap of faith with me. 

So why psychology? I've always loved psychology in high school. I knew psychology was something I needed to do and enjoyed. So I ended up double majoring in Human Biology and Psychology within the same four years, and everything worked out.

People often fear that they might be unable to move forward with something new and have to "start over." But you have a great example of how your initial work contributed to something even more than what you initially did. "Starting over" was a different way to continue to build on top of something you started and into your career. There's so much optionality out there. Until you've made that conviction to pursue your passion, you might not be aware of those options. So that was the first step: having that courage on both my mom's and my sides to say, "I want to pursue this." 

There's so much optionality out there. Until you've made that conviction to pursue your passion, you might not be aware of those options.

So how did you decide after graduation to pursue your next leap of faith by going to teach English in another country? I went into psychology knowing that future career options meant more schooling, getting a Master's degree, and eventually getting into therapy or academia. However, I didn't feel like I wanted to pursue that path.

I spent all of [my time at] university living at home, which meant hating the two-hour commutes back and forth. So it was another leap of faith to decide to build my own life and start to develop my independence and perspective. The leap of faith into studying psychology was the first step. Now, I was ready to take my second, which was moving as far away from my family as possible. I wanted to prove to myself that I could do it. I had always been interested in teaching and living abroad. I chose Korea because it worked out much quicker than other options.

What was that transition like to Korea? Korea is very technologically advanced. At that time, there was a smart board in every single classroom, so you have many tools to incorporate technology into your teaching as a teacher. I loved education tech from that angle. From that experience, I started planning small steps to explore ed-tech further.

To get into the ed-tech field, I felt I needed to know the foundations and theory and build a network. So, I got a Master's degree at Harvard's Graduate School of Education in the United States, where I fell in love with tech. Through exposure to hackathons and startups, I decided, "here's an upcoming field that I would love to explore and see if there are opportunities to apply psychology to it."

Now that you've completed your Master's, how did you make it to the first few roles in the industry? Did the program help open you up to the various work you could apply psychology to, or was it more "I'll take what I can get, then maneuver my way through?" There were a couple of paths I was looking into during my Master's program. 

One path was Instructional Design. It's very similar to product design, except you design training materials. Another path forward was going full-in on startups. During my Master's, I was involved with the startup community and hackathons. I loved the energy of it. I love the idea that a small group of people could get together and make something out of nothing within a weekend. It's wild, and this was back in the days when Tech was not sexy. We were building stuff on really dated platforms. 

After graduating, I looked into both instructional design and the startup path and applied to many jobs. The one that worked out was this startup, a storytelling platform for teenagers. I loved that there was an educational angle to it. Millions of teenagers around the world are reading, writing, and crafting their fantasies on this platform. The job, focused on Trust and Safety, was entry-level, and I didn't have any experience. It focused on resolving disputes between users. That was a very transformational experience because it opened my mind to the kind of psychology and fantasy that people have around this platform, its characters, and different worlds. This role was where I got into UX research. 

At the time, I had no idea [UX research] existed. In Canada, we had limited roles in this field. It was thanks to my manager at the time that pushed me into this role that I didn't know was possible.

What were some things you learned about the field while in this role? The magic of research is that there are people who use a product and people making decisions about the product. Often, there isn't enough visibility between the two parties. Pinpointing the motivations of the people using your products, the "whys" behind the behaviors, goals, and what's not working are all things that shape the success of a product. The first step for a product to succeed is for people to want and need it. Desirability is the first step. 

Pinpointing the motivations of the people using your products, the "whys" behind the behaviors, goals, and what's not working are all things that shape the success of a product.

Fast forward, I worked at the storytelling platform for four years. Then I went into a healthcare-related startup, then a consultancy, and now at Uber.

But overall, this theme that I keep seeing is there are different misconceptions about research. For example, some folks think of research as fortune-telling: "we'll talk to users, and our product will be 120% successful because we talk to users." Check the box! Teams tend to think that users are showing us what they want. 

So on one end, some people believe that research is a fortune-telling device—which it is not. And then, on the other end, people might think research is unnecessary because data and experiments will tell us everything. Experiments will tell you behavior, but they will not tell you the why or the context. There continues to be misconceptions about how best to leverage research and insights from customers. 

With these common misconceptions, what's another way to reframe how to best leverage research? The way I think about research is around early signals. When you think about product development, building and testing something in the field takes a lot of effort, and there could be 1000s of different solutions.

Let’s break down how to begin. First, is this even a problem that people are experiencing? We must first identify the right problem and distill them into a clear problem statement. Then, with so many different decisions that we could be making, before we even ship something, we should ask, "what are some early indications that we can get from customers about which are the right paths forward?" I see the value of research as being able to give early signals about where and what the problems are, in what context we're designing for, and what general direction we should be investing in for a solution. 

I see the value of research as being able to give early signals about where and what the problems are, in what context we're designing for, and what general direction we should be investing in for a solution.

Research is neither a crystal ball nor completely useless. When it comes to experiments, research is in the middle. It almost acts like a guiding light through a tunnel. With the right investments, we can identify the right problems and directions for solutions, so the chances of the product succeeding will increase. Thus the chances of people using the product will increase. It's not guaranteed, but at least we have a signal that it could increase before fully investing all engineering resources into building it.

Are there other times when research is appropriate? There's comfort in data, especially concrete, measurable numerical data. But the world is messy, and people are irrational. Looking at data alone does not tell you the bigger picture of what's not being said and shown.

There's comfort in data, especially concrete, measurable numerical data. But the world is messy, and people are irrational. Looking at data alone does not tell you the bigger picture of what's not being said and shown.

I'm a little worried about the growing gap between people making decisions based on the comfort of big data without understanding the context of the nuance, motivations, and qualitative side of things. This is also why I want to be that bridge to help companies humanize their customers and not over-intellectualize on just pure data.

Would it be safe to assume that companies and teams also gravitate towards what's easier to attain and access to make decisions? People love clarity; things should be cut and dry, and that's it. They love concrete answers and hate ambiguity. And unfortunately, human behavior is ambiguous. Society is ambiguous. But that's also the magic of it. We're building products for something that may or may not land. But understanding that nuance will help us better design a product that will then sell.

Moving forward is hard if you don’t know what actions to take. Research leads to actionable insights, but we need to make that investment up front. Thus, research reduces downstream engineering time, and you’ll find that certain directions are not the right ones. 

Switching gears, what advice would you give the past you who just started learning and working in the research field? Pay attention to your own limiting beliefs and work through them. The older I get, the more I'm aware of these limiting beliefs and how they affect my decisions. Many times, even being aware of them is the first step. Have conversations with yourself about whether or not these are true. Whether or not you want to take action on them. Whether or not you wish to accept them to be facts. Because often they're not. Awareness is the first step. 

Pay attention to your own limiting beliefs and work through them.

Give us a list of the top 3 things you'd recommend.

These are my top favorite hiking spots:

1. Patagonia has the best scenery. We did a five-day trek around Patagonia, which was breathtaking every step of the way. It was also disheartening to see the glaciers break apart because of global warming.

2. Iceland. There isn't a particular trail I'd recommend but driving around the entire Ring Road and spending a full week. It's amazing; it doesn't even feel like you're on Earth. It feels as though you're on an entirely different planet. Every single twist and turn feels different. One area feels like Mars, then you turn and see waterfalls and crazy greenery everywhere.

3. Banff is just pristine. No matter what type of hiker you are, there is something for everybody. It's also very family-friendly.

What's your favorite song of the moment? Or at least something you have on repeat?

I don't listen to much music but usually listen to white noise – like rain dropping on the windows.

Continue the conversation with Jing Jing. 

You can find her on Twitter @jjtan87 and Linkedin. Jing Jing also has a UX Research focused newsletter that includes deep dives on product features and UX research templates and tooling. 

She’s the host of podcast “Crazy Mighty Ladies”  that is dedicated to sharing and highlighting women who made powerful personal transformations. You can find her first episode on:

• Apple Podcasts

• Google Podcasts

• Amazon Podcasts

Jing Jing is also passionate about giving back to Ernestine’s.

Ernestine’s is a non-profit organization that provides advocacy, crisis intervention and shelter to Women, Two-Spirit, Trans, Non-binary and Gender Diverse individuals and their children experiencing violence. As part of this conversation, a donation was made to Ernestine’s.

Donate to Ernestine's