Does anyone regret being an entrepreneur?
No, but there are laments.
Successful entrepreneurs generally speaking, can only do that. Why? Why can’t they go work for someone else, collect a huge paycheck, whatever — afterwards? I think the reason is that being a successful entrepreneur actually re-wires your brain. Literally.
I believe the stress of owning all the issues, all the challenges, of almost failing a dozen times over a dozen years, does change you. In many ways for the better, but changes your brain.
I was/am an accidental entrepreneur. I never thought I was good enough to be a founder. No YC told me I could do it, nor did any mentors.
However, when I joined a venture-backed start-up that had raised $50m+ but had $0 in revenue and was close to going under … I felt I had no choice. I had to help somehow. We couldn’t fail. So I licensed some of its technology, grabbed the best co-founder on the planet in that space (who also had no dreams of being a founder), started our own company around that technology … and became a founder for the first time.
But if it wasn’t for seeing “Failure as Not an Option” … I likely would have stayed on a VP/SVP/COO/whatever track. And perhaps, been happier on some levels. I was good at that.
And maybe, if I had stayed on that path, I would have not thought about work every second of the day. Maybe, truly enjoyed a vacation or even just a weekend. Maybe, have had a true hobby. Been a better parent at the school stuff. Etc. etc.
I “love” what I do every day. I was listless, bored, maybe even a bit depressed in the downtimes between start-ups. But being responsible for everything is so hard, even now.
No regrets. This was the path for me. But, perhaps if I hadn’t joined that particular start-up, I’d be a #2 Person at some great start-up today. And maybe on some level, happier. Maybe. I was a pretty good #2.