On discovering new worlds and navigating new paths

Your creative practice can’t be easily pinned down. Do you feel a pressure to be able to succinctly describe what you do?

That’s something I’ve always struggled with, trying to figure out how to label myself. I think it’s interesting to see what labels other people gravitate towards when describing my work, because that shows me what parts of what I do are resonating with them. I usually describe myself as just a software engineer and designer, because that seems broad enough to encompass everything that I do.

How did you come to do what you do today? Was it a natural path, or were there points of resistance?

It certainly wasn’t premeditated—it kind of fell together. My original career trajectory was more vanilla software development and design. I always struggled to find a place where I could really stretch my legs and explore all the different directions that I felt drawn in. I tried doing full-time work for a while, and I just hit this wall of having too short of an attention span. I never felt fully able to dig in on client projects the way that full-time work demands of you.

So it felt more natural to break out of that world, and give myself the freedom to explore some of the different interests that I’ve always had, but never considered pursuing. For example, I played video games a lot as a kid, and in the back of my head I always had a real interest in how those games came together, what they communicated, and what people took away from them. I always thought they provided this really interesting medium for describing the world, and also proposing different ways that the world could be.

That interest culminated into the project Humans of Simulated New York, which I made with Fei Liu. After working on that, I felt like, “Okay, this is something that I could explore further.” That was the start to the stimulation side of my work.

Screenshot from Humans of Simulated New York

How did you know when it was time to leave your full-time job? Were you concerned about how you’d make a living?

Yeah, totally. As I struggled to stay focused in the office setting, I found myself stealing away as much time as I could to work on other things. At a certain point, I was lucky enough to get a grant that allowed me to actually focus on one of these side projects, so I didn’t have to worry about money and that awkward transition out from full-time to freelance work. It all lined up, in that I just applied for this grant and I got it, at the same time where I was really struggling with staying meaningfully involved in my full-time work.

At this point, how do you balance money-making work with grants and other types of income? How do you ensure that your situation is financially feasible?

It’s always a challenge. There are a lot of jobs that I take that don’t necessarily align with my interests, just because they pay. But, fairly often I get lucky and manage to find some kind of paid work that’s in line with my personal interests. Grants definitely make it a lot easier, because you get to propose a project, so you have quite a bit of control over what exactly you’re going to be spending your time on. And, in my experience, getting a grant is just about as hard as courting a new client for a freelance project.

For me, it’s really been a matter of finding people and institutions who have similar interests and who are interested in supporting the kind of work I do.

How do you initiate working relationships with organizations? Do you tend to seek them out, or do they tend to find you?

For the grant process, it’s usually me looking for them, or people forwarding things to me, or through word of mouth—that kind of thing. Directly approaching organizations is something that I’m trying to figure out how to do right now, because a lot of the organizations that are doing interesting work with simulations are associated with the government, or are more stodgy and bureaucratic.

For instance, something that I’ve been really drawn to is agricultural technology and simulation. I want to develop simulations of crop growth based off of weather conditions and so on, to figure out what needs to change with water distribution. But, I have no connection to that world at all. Figuring out how to navigate this new space so I can actually start approaching people and not get laughed out of the room is a current challenge I’m facing.

When you’re entering a whole new community that you don’t have any real touch points in, how do you go about getting to know who and what you’re dealing with?

There’s usually a research phase, where I spend time figuring out what the main institutions in the space are, big and small. I’ll try to figure out who’s doing work that is particularly interesting, or that seems like it might align with my values. I’ll do some cold emailing, and I’ll try to show up at their events, that kind of thing. I just try to weave myself into their community.

That’s actually part of the process I really enjoy. It’s very exciting to enter a whole new industry or space, and go through that process of gradually filling out the map and landscape in your mind. I like trying to understand their perspective, the problems there, and how people in that space evaluate the major shifts that are going on in the world.

What is the responsibility of creative people to engage with things on a more critical or political level, like you tend to do? I’m also curious how you define success with a critical or politically engaged project.

I think we all have a responsibility to engage with political issues. The challenge is really figuring out how to successfully do that. That’s something that I struggle with a lot. What I struggle with in particular is convincing myself that any of this work functions meaningfully as an actual intervention.

A big part of the challenge is the distance between myself and the problems that I’m trying to directly engage with. With the agriculture example—with the politics of food production, food distribution, and food waste and all that—it’s a totally new space to me, and it’s a little presumptuous to think that I could find any way to become meaningfully involved.

In terms of actually measuring the success of a project like that, I feel like Bail Bloc is a good example of a fairly ideal outcome. Going into the project, we had a few goals in mind—one of them was to actually generate a substantial amount of bail fund money and bail multiple people out of jail, and the other goal was to get people thinking about the issue of bail and mass incarceration.

In this particular example, it was interesting to get the cryptocurrency community—who on the face of it has no relationship to the concept of bail, but who does have a relationship to future systems of financialization—to actually consider the idea of bail as a problem.

Screenshot of the New Inquiry’s Bail Bloc

Do you tend to make a set of goals for all of your projects?

I don’t explicitly write out goals for every project, but while I’m working on something, there does always tend to be a few things that I’d like to see happen. With The Founder, for instance, my hope was that people working in Silicon Valley—like designers and engineers working at Facebook or Google—would play the game, and would then reflect on the experience. So that was definitely a goal, even though I never wrote it down or anything.

When you’re getting started with a new project for which you have an outcome in mind, how do you zero in on the mechanics, the design, and that sort of thing?

My process is pretty chaotic, and I don’t really have a way to articulate it for that reason. One general theme is that the ideation phase centers around an idea that just feels right. Usually, once I do actually hit upon something that feels really right, the rest follows more naturally. Once a project has enough momentum where I know which direction to start going in, I’ll start sketching out ideas. And then I’ll just keep pursuing that for a few days, and see where it leads.

How do you keep your schedule balanced? How do you decide which opportunities to take on, and which to say no to?

That’s also something I struggle with. The way I’m dealing with it right now is that I have income requirements that I try to hit, so I take work based on those. Also, if a project seems like it’d be really fun to work on, I’ll do my best to make time for it. The consequence of this approach is that my time management isn’t great. My schedule sort of ebbs and flows between having too much to work, and not enough work.

It’s also difficult to carve out that essential time to not do anything, and to just meditate on the stuff that I’m researching. I think that’s probably why the ideation phase is really difficult for me, just because I’m often distracted by other work that I have to do, and by other responsibilities. To do my best work, I need a stretch of uninterrupted time to think things through.

Screenshot of The Founder

I’m curious to hear more about your approach to taking breaks, and making sure that you don’t burn out.

For me, there’s another thing I have to balance, which is that I often get really bad migraines that will incapacitate me for a couple of days. Having the threat of that looming over me motivates me to prevent myself from burning out or overworking myself.

In terms of other strategies for not burning out, I try to bike everywhere. I like that because it works as a time to just zone out. I’m also protective of my weekends, and all the other typical types of work-life balance stuff.

What have been the most important practical or business lessons you’ve learned as a creative person?

It takes a lot of work to get work, and to stay afloat financially, which kind of sucks. Freelancing and doing creative work comes with a lot of freedom and independence, and that’s worth a lot to me personally, but it also means that I’m responsible for so much more. Keeping track of the business side of things has actually taken away from the time that I have to really focus on my purely personal pursuits.

The main lesson I’ve learned is that you just have to take a lot of shit work, unfortunately. I would love to be able to exclusively write games and make simulations, and I’m lucky enough that some of that kind of work is coming through, but it’s usually at a lower pay, and is just very rare to find in general.

If you could go back in time and give yourself one piece of advice, what would it be?

I think I would have told myself to work full-time a little bit longer and have a better plan for transitioning to freelance. When I was doing full-time work, I was in a much better position to find clients that would be able to pay pretty well, but I didn’t have any of the foresight to know that at that time. I’m sort of trying to make up for that right now.

With Seven on Seven coming up, I’m curious: what do you think creates the mechanics for a really positive collaboration?

For me, something that tends to help is having overlapping interests, but coming at those interests from completely different perspectives. I’m excited about the Seven on Seven collaboration because Sean [Raspet], my partner for this, has a similar interest in food science and agriculture, but he’s coming at it from a chemistry and food science perspective, which I have absolutely no background in. Since I have no sense of what that space is like and how people from that world think, I’m really excited to see how our different skill sets and frameworks for thinking about the world will align or not align.

Something I look for with all collaborations is to learn from the other person. I like to learn about what kind of conceptual tools their background has enabled them to develop, and to understand what insights I can take from their perspective to fuse into my own work. Another advantage of collaborating is it allows me to work in a new medium, and to try out some new things. With Sean, he works a lot with growing algae, and I’ve never done anything with plant-based mediums, or with growing as a medium. So I’m really excited to see where that could take us.