Why your side project is more than a side project

(If you want it to be)

Your current life has to make room for your next life. That’s a design problem, and it’s your most important one. Not “how do I make a living now” and “how do I figure out what’s next” as two separate questions. One problem. One solution: a life with some wiggle room in it.

I figured this out in 1993. I was thirty and working as a news artist making charts, maps, and infographics to run alongside stories in the paper. It was a good job. But the newspaper industry was also in visible decline, and it was clear I wasn’t going to retire there.

So I quit. I moved cities and took a part-time teaching position at a university. The pay was less than half what I’d been making. The job was term-limited: three years, then it was up.

From the outside that looks like two bad moves. Less money, less security, a clock ticking on the whole arrangement. From the inside it was the opposite. The part-time work was the wiggle room. The term limit was the pressure. Together they gave me a container to build the next thing inside.

That wiggle room became a side project, which then became a multi-million-dollar company. I sold that company in 2022 and now I’m doing it again. This time I’m doing it with friends, which makes everything a thousand times easier and more fun.

If you want to create this kind of wiggle room for yourself, that’s exactly what the School of the Possible is designed for. A space for play and practice and small creative experiments that not only bring you joy but open the potential for your next life.

I can’t guarantee where your side project will go. There are no guarantees in the creative life. But it might grow into something interesting. And if you don’t make room for side projects in your life, then you’ll never know.

I want you to experience what this feels like, and to make this as easy as possible I’m setting up a two-week free trial. No credit card required. Try it for two weeks. Cancel anytime.

Access your free trial here.