Steering a creative, independent career with Kevin Twohy
Meet Kevin Twohy, an independent product designer helping early-stage startups go from zero to one.
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.
Interviewed in November 2020
Tell us about yourself and your creative journey.
My name is Kevin Twohy, and I’m a product designer. I’ve always loved tinkering with computers like playing around with code which is what got me interested in software in the first place. When I saw the spark of making something from scratch that you could then hand to someone to use, I loved that. And through that, I learned, by accident, that doing user interface design was even a job.
I vividly remembered where I finagled my way into working at a startup that made consumer software. At that time, I was doing prototyping, getting user feedback, and working on giving a sense of where we could go. I shared many ideas, and at one point, I remembered early on that the VP of product asked me, “Can you sketch out what that idea would look like?” I sketched out a flow diagram and essentially wrote the engineering spec. He responded, “Yeah, but can you sketch out what you mean?” I thought, “It’s all there in the doc exactly how this is gonna work.” And it finally clicked for me that he meant for me to draw a picture of what it would look like on the screen.
I couldn’t believe that was a job! At that moment, I thought, “I bet I could figure that out.” And so, I downloaded Omnigraffle, and I was off to the races. I started devouring everything I could find about design, user experience, and user interface design. I had a total deficit of anything visual, so I was hanging out in wireframe land. Even just the idea of, “Come up with a theory, validate it, and use rectangles to flesh out what the software is going to do. And then someone will build that, and it’ll be real…” lasted me for years. It was very satisfying.
What happened from this point till now? This whole time, I’m immersing myself in the world of design, devouring anything I can in books and online. I did a stint in the agency world, which was like the big leagues from my perspective because they’re big Fortune 500 type stuff. I learned within a week that I knew this was not meant for me. I spent a total of maybe two years in the agency world.
I stuck around because, within the design work, something adjacent was pretty interesting that I didn’t know how to do yet. It was the business of selling design and painting a story for the client. It’s a required skill that can be very difficult to learn.
So while the type of work I was doing wasn’t right for me, I learned how to sell a point of view and build a case and the relationship between business and design and money. Afterward, I decided I wanted to be closer in a tighter loop to make something instead of selling a half-million-dollar PDF and hoping something would get built.
I worked at a couple of early-stage startups for several years, often as the first designer. I tried to stitch everything together that I learned to get going and get a product idea off the ground. Most times, I also would hire a design team under me. I did a few cranks of that.
I love that early process, and in a couple of cases, saw what happens after that early process of going from zero to one. At that point, the job becomes about other things like hiring and managing a team. Or making sure we’re driving towards quarterly goals and other things that come with a medium-sized company. I never really got that interested and kept wanting to go back to the beginning.
So that’s where I started to go independent. I wanted to decouple full-time employment from building a product to have a little more granularity with where I was steering my career and interests. I got this idea about how I have pretty good intuition at that early part of product development and that’s the part of the process that I love the most. And if I could figure out a way to only do that part as my job, I would love that. So I wasn’t even sure that it would work out well or be viable, but that’s what I was setting out to do. And that’s what I’m doing now.
When did you know that you loved and then also wanted to pursue this career? I saw this pattern occur a couple of times in a row when I was at early-stage startups. Specifically, that excitement of getting an initial idea working where most people assume it keeps getting more exciting as you continuously iterate and build the small startup to something larger—it doesn’t always work like that. That particular type of excitement often stops at that early stage with a small number of people working in a really tight loop on something. You then bring a user into the loop and keep going until you get something new into the world. The excitement of that specific moment is totally finite. And once it starts working, it’s actually kind of done. After that, the work becomes something else, such as hiring and managing teams. I had that happen a couple of times where I started to realize I’m spending my time and my energy doing other stuff, and I just don’t enjoy it as much, and frankly wasn’t especially good at it.
One big challenge that I see many people face is that you learn in your career to be quiet about stuff that you don’t fully understand or just doesn’t make sense to you. You might think that people know what they are doing since they’ve been around longer. And so you learn to tolerate that. However, I started to have this suspicion, like, “you know what, I had quietly thought this makes no sense at a couple of points of my career.” And it turned out that that instinct was right, but I never spoke up.
It feels like you’re gonna be a bad designer for saying out loud that you don’t care about this type of managerial stuff that happens after the early stage. But I felt, in my gut, I know what I like and care about.
I also found that it makes more sense to me that to learn and practice something, you have to do it a couple of times, again and again. And you try to find all the variables and figure out what’s different about the next time and come up with a general theory of how to get good at it. If you work at a company, or maybe you have a few several years stints at a company at best, you only really get to do that three, four, or five times in your career. Ideally, I would do those dozens of times over and over. So I thought that’s what’s intuitive to me, and I’m going to try to do that.
I also found that it makes more sense to me that to learn and practice something, you have to do it a couple of times, again and again. And you try to find all the variables and figure out what’s different about the next time and come up with a general theory of how to get good at it.
My plan up until a couple of years ago was that I’ll give this a shot, and then I’ll swing back into a company because I thought I’ve got to come back to the company’s safety net at some point.
However, I’ve been rewarded enough personally by the work and learning that it’s not to say, “I have solved the theory of how to be a creative, independent designer,” but it’s enough to keep going. And it’s enough to not feel like I’m giving that much up by being out of the tech corporate ladder to keep going.
Would you say you’ve accomplished what you set out to do? Think of it in stages. The first stage was, “could I even get someone to hire me?” There are enough challenges inherent in that. If you can get across that stage, then it’s “can I get enough people to hire me with enough stability and frequency so it can be my job?” And be as good or better of a job than the last full-time job I had. I feel like I’ve crossed that stage.
I’m currently at this stage where I have a more granular rudder where work is the baseline, but I can also decide where I want to go next, to be able to steer wherever I want to go. That, to me, has been my main goal. And if I can live a long, happy, creative life doing this type of work that people will pay me for, I’ll be satisfied. I started off doing wireframes and now I spend my time working with founders going from zero to one. If I were designing book covers in four years and creating an identity for a museum, I would be thrilled. I think of it all as a way to be flexible about how I steer and tweak the rudder more often to get where I want to go.
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I’ve always admired how you’ve taken control of your career, especially as an independent designer. Any advice for folks starting out? Trust your instincts about what you like and what you don’t, what you think makes sense for you, and what doesn’t. Not everyone is the same, and it becomes more difficult as you start to get further along in your career.
Trust your instincts about what you like and what you don’t, what you think makes sense for you, and what doesn’t.
Honestly, it can also be incredibly difficult to trust your instincts when there isn’t a path laid out. When you get deeper in your career, it’ll be challenging because you’ll start to have intuitions about aspects of the work you may not like and suddenly see that there’s no other way to go. If you’re able to, trusting your instincts earlier on and going in a direction that makes sense for you goes a long way.
What are you spending most of your current time on presently? I’m mostly working on these zero to one consumer software projects where I start with a founder from the very beginning. We begin to do some definition around what we might build. Then, put some structure around it, build a prototype to test and learn, refine, and get it out into the world. We may do a couple of cranks after that once the product is in the hands of users.
Most of those projects can last in the shortest a couple of months. At the longest, like MIRROR, can last like years. Sometimes I’ll do that inside larger companies like The New York Times. It’s basically zero to one project inside a larger company that wants to build something from scratch.
I have also been interested in drifting away from software and exploring more purely graphic design projects with a defined start and end. I’m working on a book cover design right now. I would love to do more of that type of work and mix that with the software work.
Why is it important to you to do what you’re currently doing, both career and project-wise? It depends on your lens. Personally, I think people should be more selfish, in general, with their creative energy and what they want for themselves. For example, I genuinely love doing design work, precisely doing it actively where I’m in a state of enjoyment at most times. If I can do that and get paid for it, then I feel I’ve been able to steer the ship where I want to go. That is more than where most people are lucky enough to get to, so that could just be the end for me.
Personally, I think people should be more selfish, in general, with their creative energy and what they want for themselves.
In the end, it all matters because it’s enough to make me feel personally fulfilled, plus it pays the bills. If the project ends up making a successful business outcome, that’s interesting. If it ends up making someone happy or helping them in life through the software I create, that’s a bonus.
I’m also interested in pushing towards more durable design work. Half of the successful software stuff I’ve worked on is completely gone. Even the stuff that’s successful now might not be around in a few years. I don’t think the disappearing matters the most as it’s part of that continuous history. Some types of work stay a while, so it’d be interesting to explore what that could be for me. For example, if I could land the right note with the book cover project, it could last for decades. Maybe 10s of millions of people will see it, and it’ll have some effect on them. The project would start and end with me, but it’s just the beginning in terms of its impact on its people once I’m “done.”
Are there any misconceptions about the industry you’re in, or the work you do? I’ve talked to many people who have reached out to me who want to go freelance but struggle with trying it.
There are two common themes. The first is that they’re worried about stability and the “feast or famine” cycle of it, which is totally true. People don’t get to hear enough about how to set up a stable, predictable structure. For me, most of my projects last about a year, and I work on a couple at a time where the projects have their own cadence. I always know what I’m working on next from six months to a year out. In some ways, it may potentially be more stable than a full-time job because you’re not stuck in one company that may go out of business. But again, this might not be for everyone.
The other theme I hear is folks expressing they really like being on a team and that interaction of being in-house. And that is very real. I totally empathize with that. But I will say, if you work on these projects for a year or more, I personally feel like I’m part of the teams that I have been on. In some cases, I’ve been working with them for multiple years, and there’s no way to get any work done without interacting with them daily and being embedded into the team. So while certainly there is a lot of freelance work that’s external and you “throw it over the fence,” there is a path that you can work on a team without getting a W-2.
My team and I have gotten to work closely with Kevin for a year now and I can’t say enough about the quality of strategic product thought and creative output he brings to the work. He continues to be a core team member for us. Also, A+ jokes. Need some help? Have a look https://t.co/wtmMgVYvIG
— Alex Rainert (@arainert) December 30, 2020
When I hear objections from people such as “I want to embed myself into a team,” I’m hearing that team dynamic, not throwing things over the fence, and seeing things to completion is essential—so just do that. Don’t take on projects where you’re going to be off to the side, etc… Be upfront about how you like to work with yourself and clients, so they know how to make the most out of the engagement. People are willing to be flexible, as long as you do quality work, are reliable, and a nice person to be around.
Be upfront about how you like to work with yourself and clients, so they know how to make the most out of the engagement.
Sounds pretty full circle to me, from how you’ve started going independent to get better control over steering your career and now to be able to set up in a way that works best for you and your client! It’s tough when you’re starting to know which way you want to go and have the confidence to assert it. So it might take a few reps to learn that. Right, it’s like the design process where you learn and iterate. It’s almost like setting up a hypothesis for each step of your career, testing, and validating as you go.
Is there any other advice you would tell yourself when you started going independent aside from trusting your instincts and getting practice? Besides being an individual contributor and learning the core work you’re doing, widen that and figure out what other adjacent skills or experience are there that people are willing to pay you for. That could be you’re a great visual communicator, have stellar writing skills, etc. It would be the type of thing your friends would call you for advice on or treat you as a trusted source. That’s the stuff you can use to become a subject matter expert that ends up being higher leverage than just selling wireframes for money.
It also means that you become more unique and have fewer competitors because there could be thousands of people who sell wireframes, writing, graphic design for money. But as you hone in on your unique set of skills, more people will want to hire you for that unique combination.
Also, if you can diversify and find a way to bring more of your whole self into it. It also gives you more exit strategies where you’re like, “okay, I hit the end of the road on this particular aspect of what I’m doing. So I’m going to go 10 degrees to the left and build out this other part of it.”
I wish I had this advice earlier in my life! Me too! (laughing) I wish that the independent path was more visible and seen as a viable track for the long term, not just for a short stint. There’s a vast chasm you have to jump over in the first 12-18 months of it. But, if you can get past that and build up the confidence and muscle memory, it’s possible. If this was more visible and more people could see it as a real example, that would make it so much easier for other folks to get started.
Give us a list of the top 3 things you’d recommend.
A *New* Program for Graphic Design: I’ve been interested in going back to basics and giving myself a fine arts degree via the internet. It’s adapted from a lecture at Princeton, so it reads like you’re in class. It’s also a quick read, and I reference the bibliography to find more books to read through. Also, I’m currently in a back to fundamentals mode to “learn the rules and break them”.
How to With John Wilson: This show is strange and beautiful, I’m not sure there’s anything else like it. Man-on-the-street comedy meets visual free association meets….something else. If you’ve been missing wandering the streets of NYC, this will help.
Fave song of the moment or what do you have on repeat right now?
Sun In An Empty Room by The Weakerthans. I’m deep in the podcast world right now for one of my projects. It’s the theme song of a great podcast called Heavyweight, which I like a lot (both the theme music and the podcast itself).
Continue the conversation with Kevin.
You can find him at kevintwohy.com and on Twitter @kevintwohy.
Kevin is also passionate about giving back to Shatterproof.
As part of this Conversation, a donation was made to Shatterproof, a national nonprofit organization dedicated to reversing the addiction crisis in the United States. You can also support by donating directly.
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