I grew up in a place I don't want to return to. Also, I have two handicapped kids, one of whom will need round-the-clock care long after I'm dead. I got sick (at 21) of crappy bosses. And finally, I chose a good field to work in (programming)
I became highly self-motivated at 21 because I was a dropout & knew I had to be better than my degreed peers to get an equally good job. It was either go to college, then get some crappy job as a teacher, or find an area of programming so challenging that it scared other programmers (back then, it was embedded systems and compiler implementation).
Ever since I decided at 21 to become a programmer (despite having absolutely no tech background) I have studied for my next job while I'm working the current one. At 34 Microsoft hired me with no resume despite the fact that I was old and the last thing I graduated from was middle school.
One thing I always keep in mind is this: are there people dumber than I am doing better than I am in whatever I happen to be doing at the moment? If the answer is yes, then I know I can be just as successful simply by working as hard as I need to until I'm as good as they are, or maybe a little better.
Have been CEO of my own company for 14 years now, but continue to study current programming practices and to do interesting projects with them. No matter what job I have had, no matter how good, I have always operated under the assumption I could lose it all tomorrow, and that I would be facing stiff competition for jobs.
I avoided Silicon Valley because it was too much of a pressure cooker. Instead I lived in more laid back areas that still had some tech presence. This let me live a moderately balanced life despite essentially working 2 jobs at all times. Had I gone to Silicon Valley I knew, even in the late 80s, I would be slave to an 80 hour-per-week job and end up, in all likelihood, with nothing to show for it.
I read the industry and business press carefully from afar & kept a close eye on what was doing well and where the market was underserved. I tried to match my skills to holes in the market. My approach can be scary because I have to take on more risk, but the rewards have been better.
Because of this I invested lots in Microsoft stock in the late 90s when everyone said they were dead. Their past, and their P/Ls, said something very different. The stock I owned went up 1300% during this time because everyone else, including Microsofties, was trying to get out if it. (I exited at the peak.) This money helped me invest in the business I own now. It was also a risky buy at the bottom of a market.
I have more than one paid-for house and no debt but I still keep up my skills.
Though my income is very good, even in my 50s I am ready to work as a developer or architect if my company shuts down tomorrow.