What game do you want to play?

I’ve been working on some of my own software ideas since September 2022. I’ve loved parts of it, but I’ve struggled with feeling lonely and ineffective, especially surrounded as I am by Silicon Valley hustle culture. Am I just not hustling hard enough?

In Working, Robert Caro describes how he had been working alone on his first book for five years, and he was feeling really bad about how long it was taking him. The people he knew would ask him if he was “still doing that book”. Eventually, he was admitted to the Allen Room at the New York Public Library, where he met other writers who didn’t balk when he said how long he had been working on his book, because they had taken similar lengths of time to write their books. Hearing this “wiped away five years of doubt”.

I’m really glad I learned about this book so I could read that story. It really resonated with me and has helped me reflect on what I’m doing. If I compare myself to a hustly startup founder, I’m going to feel inadequate and full of doubt. I can easily see myself hitting the one year mark this September and wondering if I should throw in the towel. But after reading this, I started reflecting on what I’m actually trying to achieve working on my own software ideas. I realized that my primary goal is not, in fact, to start a company. I’m more motivated by craft and solving complex problems at the intersection of design and engineering. If a company is necessary to achieve that goal, sure I’ll start one.

This perspective shift is really helpful. Instead of thinking I’m a “startup founder”, I’m now thinking I’m more of an independent software developer. I’ve stumbled across others on Twitter who are taking a similar approach to me - they are not dead-set on starting a company, but they are building cool software tools they’ve wanted to solve for a long time, and the journeys they are on often last years. There are others designing and building software at interaction design research labs, and still others running bespoke software agencies focused on complex UI problems. These people are are following paths more similar to the path I find myself on.

For some reason, the word “game” came to mind. Now that I have a better idea of the game I’m playing, I also feel this desire to meet others playing a similar game. I haven’t yet met anyone, but at least now I know where to look!

One could of course tell me to stop comparing myself to others and to do my own thing. And sure, that sounds right, and I’ve told myself this often, but it doesn’t really help calm the feelings of doubt. What does help calm those feelings is seeing other people playing a similar kind of game to the one I’m playing and realizing that they either have felt or do feel the same way that I do.