I remember the day I realized who I wanted to be very clearly. I was sat in the Matter San Francisco garage, watching a panel of entrepreneurs from previous cohorts give advice to the current set of six startups who were about to graduate from the program. As I listened to the advice from the sidelines, as a member of the Matter team rather than a founder, an overwhelming sadness began to take hold.
It shouldn't have: Matter was a dream job that allowed me to support a particular kind of mission-driven startup founder. I loved every minute of it. But at my core, there was a part of me that missed building. Through supporting these 75 companies, I understood the mistakes I'd made more deeply, and knew I could do better next time.
I also knew myself better than I had the two times I'd been a co-founder. The truth is, I have a problem with authority: I hate being told what to do, and I'm not interested in perpetuating existing hierarchies. Starting my own businesses has been a way to create a working environment that's mine and mine alone, in a way that being an employee or a contractor never could be. I get to set the culture; I get to set the mission. It's a very individualist way of looking at work, but I'm not sure I can be different. Establishing a protective bubble that allows me to think in the way I need to has been important. It's a double-edged sword: external accountability also turns out to be important, and is harder to come by when you work for yourself.
I didn't go out and become a founder again. Instead, I've found a way to give myself creative space by working on side projects, which are never businesses and sometimes have nothing to do with technology at all. That doesn't mean I won't eventually start something new, but it takes the emotional pressure off a little. I get to work on something that's entirely mine, on my own time, with nobody telling me I should do it a different way, and without the pressure of it having to raise money or be self-sustaining. I've found it to be a very good balance, and it often helps my day job work.
Ultimately, the reasons I felt misgivings during the Matter panel were tied up in my identity. I am a founder: I make things using effort and creativity. That's not a million miles away from being an artist. But it's very different to being someone who has spent a long time going deep on a single career path serving other peoples' businesses. That might be where I am, but it's not how I see myself, and it doesn't cut to the core of the work I do. I've learned I'd rather earn half as much money to have twice as much freedom.
I've found it useful to bring that attitude to work. I'm in service of a mission that I've bought into, but take a critical eye to the vision and strategy. Is it the right thing for the people I want to help? Is it meaningful to work on? Is it intellectually honest? Going in and treating the company as if it was my startup to shape by definition means I'm unlikely to go with the flow, for better or worse.
I suspect most founders are the same.
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