I went to a specialized high school (as a semi-anonymous account don't want to give too much detail), and as such more than a few of my close high school friends went on to be famous in their chosen profession, and a couple starred in some fairly well known movies. I ended up going to a top university, and one of my roommates ended up founding a successful internet company you've all heard of. My first job out of college was at tech company with a "boot camp" like training program for new recruits. One of my close colleagues eventually co-founded a financial trading company that made him phenomenally rich in his late 20s, and another colleague founded a well-known unicorn.

Perhaps because I was inculcated fairly early in a competitive environment, it's hard for me to look back and not woulda/coulda/shoulda it. Mainly I'd like to ask some of my successful ex-colleagues and friends (some of whom I'm still in contact with, so wouldn't be too hard I guess) if they have any significant regrets. One on hand they must know how incredibly lucky and fortunate they've been, but of course their lives have their own trials and tribulations. And my life is good, I have close friends and family, quite mundane, though at least a good mundane. But still, I find it hard sometimes to not at least wish for a future reincarnation, one where I have the natural talents or extra drive or whatever that is needed to grab that brass ring.