First, let me say that I am happy where I ended up. I'm successful, enjoy my work, and when I compare my personal income with our family income when I was growing up, it is an absurd multiple.
We were a very poor family in a poor part of the South. I went to a top-10 small private university on a full ride, felt completely alienated and never quite figured out how to function in that environment. I dropped out and moved to San Francisco at what turned out to be a very good time (early 90's), and once Netscape dropped, discovered nobody else knew what they were doing with this web thing either, and more or less faked it until I made it.
At the same time, I have had and do have ideas that others have executed on, that I know I could have made a go at, if only…
The if only list is long, and most of it comes back to self-imposed limitations that I can trace back to how I grew up. Frequently it relates to economic security, but there are other habits of thought that stop me from even getting to worrying about that.
One big one is that I never learned to think about entrepreneurship. A big lesson hammered into me growing up was the importance of "finding a good job", not figuring out how to make my own.
I did start a company in my mid-30s, and we did OK, until we didn't. And that failure (I think) had nothing to do with the habits of thought of a poor kid. But failing in a similar way in my 20s would have left me in a position to learn from that and try again, something I'm unlikely to make a go at 10 years later. I do little things for side income, but those are hobbies.
So it ends up being this thing that doesn't really bother me at this point, but does leave me to wonder what would have happened if I had picked parents from a very different walk of life.
And I am quietly amused when people tell me how they built everything themselves "after a seed from Dad", or "with a great connection I made through a family friend" or similar. Those are impossible blockers for a lot of people, even if they get over some of the habits of mind better than I did.