This is very similar to my path. I grew up poor and had a bad time in school, so I didn't make it in college as well. Once I started working in the industry though, I went all in all the time. Made myself the kind of engineer that people from startups around. Became a manager, a co-founder, a director, and was incredibly close to accepting a CIO/CTO role. With each goal I found I was less and less happy, eventually I took a boring job at a consulting firm that works with boring industries and Fortune 500 types. I'm a principal engineer and architect and it's boring as hell but it pays incredibly well, is super stable, and I get to go train bjj for 2.5 hours twice a week during the middle of the work day. I'm happier than I've been since I landed that first programming job.
> With each goal I found I was less and less happy, eventually I took a boring job at a consulting firm that works with boring industries and Fortune 500 types. I'm a principal engineer and architect and it's boring as hell but it pays incredibly well, is super stable...
I relate with this a lot. Maybe it is that I burned out or its my Age (40 later this year), but after being 8 years churning along in startup leadership (as tech lead and then Head of Engineering in two startups), now I accepted an "Architect" role which does not have all the craziness of being "in charge" of the whole system all the time, and "herding cats" managing people. I am SO HAPPY now I cannot believe I landed this role, and I hope I keep it for some time.
I think the only time I am going to "run very fast" is if I make my own company. Which won't be VC backed (in all these years in VC land, I've not liked the VC model).