Actually, I am not young. I just retired and have been thinking about my life, career, etc. I do not have a disability (my wife may disagree) and I agree it makes life more challenging (wouldn’t be called a disability otherwise). I also agree with you that life can be hard, children are born with health challenges, children make poor decisions with terrible consequences, spouse dies, you get cancer, etc. We all need to get through these. That does not change the fact that we all have decisions to make everyday about our careers, our families, our health, our financial situation, and so on. When we look at those who made different decisions, it does not necessarily mean they made better or worse decisions, just different decisions.

I have been thinking about this a lot recently. A former boss and good friend who is incredibly smart and effective in the work place asked why the two of us had never gone the PE route and been more successful. While he is very successful by most standards, he sees people flying private jets all the time who do not appear more skillful, yet have been more successful. As I think on this, I feel I simply was never willing to go all in on the risk required to achieve that level of financial success. I tried co-founding a company once when I was 28 while engaged and importantly, before children. I felt I could take the risk and if I failed, could bounce back. I did fail - company did ok but my I ended up disliking working with my senior partner - and I did bounce back, ending up at GE.

After that, I did not feel comfortable taking that level of risk until my children were off to college and no longer dependent on me an I had enough money saved that my wife and I would be ok for a long time. The people I know who have been jet-money financially successful took huge risks. They were all in on their venture(s). Frequently this cost them their marriage and/or relationships with the children. This was their choice. Their cost/benefit analysis to optimize their success criteria. Some regret the decisions - they underestimated the effort and impact on those they cared about. However, most have not. They are happy with how things have turned out.

Different strokes for different folks.

The other factor you are missing in your analysis of PE route is the number of musical chairs are limited. There can only be 1 taylor swift not millions. So the choice is not for everyone. Even if everyone made that choice, a million taylor swifts will not happen. Surviorship bias is real.

Great point

It sounds like, by and large, you've had a pretty good life. But please understand that, while you've made good decisions and have taken advantage of the opportunities in front of you, a large chunk of your success comes down to random chance.

Many people do not fall on the good side of that random chance.