A conversation with a friend prompted me to think more deeply about what motivates me work-wise.
For me, it comes down to these things:
Starting something is a way to choose who you work with, and who you serve through the business (or nonprofit, or open-source project, or whatever flavor of “doing your own thing” interests you).
Who I work with is a huge factor in my work happiness and work motivation. And the biggest factor (by far) that shapes the company, the product, and the culture is the people that are part of the company.
The idea that you are personally responsible for things happening (or not happening), and for things going well (or going poorly). And that you have a lot at stake: you gain a lot when things go well, and lose a lot when they don’t.
The feeling you have the freedom and ability to act on an idea. A lack of agency is very frustrating: I feel stuck, unsatisfied, and demotivated.
I love learning, and there’s no better way to learn a lot of different things (in my work sphere, anyway) than trying to start something new. I also enjoy breadth of learning (vs depth).
Balance is important, with family and friends and health and hobbies and everything else life is made of. Work isn’t everything, it’s not even the most important thing — but it is something, and can be a meaningful part of overall happiness.
Somebody asked me recently if I was a “serial entrepreneur,” and I said “I don’t think so. It’s more that entrepreneurship is the only thing I can think of to do that I have a chance at being happy with.”