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GGGP here.

I probably could have skipped my 5th startup, but psychologically, I couldn't see myself as retired. Startup #4 was, for a time, the most stressful job I've ever had. My part was distributed, and I was dealing with all the gotchas that entails, and these gotchas were being uncovered at a high rate, thanks to a stellar system testing guy.

And then, suddenly, the last serious distribution bug was solved, and the system was working, rock solid. And I glided, through the acquisition, and then for a couple of years with our new corporate parent. Interesting new development stopped, and it was all about maintaining a working system. They knew they couldn't keep people there with interesting work, so they threw money at us. And it worked for a lot of people. Me too, for a while, until startup #5 came along, and it was really interesting. So I left.

But #5 was poorly conceived, and had other difficulties, and it burned me out after a few years. A really deep burnout -- I was angry all the time, and couldn't get myself to focus on work. I figured that 25 years of startups was enough, I was able to retire, so I did.

I do sometimes struggle to keep myself occupied. I've done a couple of minor software projects, but it is difficult to motivate myself to do something that has already been done, and that nobody really needs. I have also found it difficult to motivate myself to get into new (to me) areas, e.g. machine learning. There is some amount of depression going on, for sure.

I did consider going back to BigCo, but: I really enjoy having the freedom to travel where and when I want, the lack of stress, and all the other obvious benefits of not working. But the major reason is this: If I am bored and don't know how to fill my time, that is a fundamental problem. Doing some random task for BigCo doesn't fix that problem, it masks it. I need to figure out what it is I want to do.

I did find one fun project: I decided that I really needed something that didn't involve sitting in front of a keyboard. So I decided to build a sailboat. Having no experience with woodworking, I opted for a kit that includes pre-cut wooden pieces, and it's up to me to glue, and sand, and varnish, and paint. Sort of like building a model, like when I was a kid, but on a bigger scale. Surprisingly difficult, for me at least.



Really interesting perspective. Thanks for sharing.


Thank you so much for your answer - all very interesting!




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