I chose the wrong school because they accepted me, and my high school counselor thought I had zero chance. I couldn't afford it, and dropped out. I would have gone much farther studying computer science at Purdue Calumet, and could have had it all paid for.
Once I had the Windows NT 3.51 server drive mapped as D:, and got confused thinking it was a local drive. Had to drive 25 miles and rebuild things in the middle of the night, sweating bullets. We were a small ISP with 200 customers, I was the tech staff.
My next to last big mistake was staying at a system administrator job far longer than I should have.... they really didn't need someone full time, and it zapped my drive to get things done.
Then I took a job making gears... the pay and commute sucked, but I liked doing it. 5 years away from technology, then Covid hit, I got sick... and I've been tired ever since.