It seems like everyone who has retired, or is looking to retire, is of the mindset, “When can I stop trading my time for money?” Based on that strict definition, I retired in my teens.

I have never understood this mentality. Baffling to me. Also, invest in yourself or your own entity, not someone else or their entity. Will change your life.
So, this past weekend... Actually Sunday... I flew CLT <--> ORD to attend a memorial service for a 26 year old young man who played lacrosse on a number of teams I coached. I think I met him when he was probably 10. He was on my first team I coached.... and I had many years of spending time with him and his family. Those of you know who know me a bit know that I've had a number of kids who I had the pleasure of coaching through youth ball and through club ball while they were in HS. (note: I intentionally did not coach these kids in HS so as to get other coaching and having spent this time with these kids, I never wanted their HS coached to be second guessed. My own kid is included in this mix.)
Three of them. All kids I coached, made it through college, gainfully employed and valued members of our community and were downtown Chicago... grabbed an Uber to get them home. Drunk driver on the Eisenhower caused a three-car collision. Killed one boy, sent another to the hospital. Third walked away.
Seeing probably 50 kids at a funeral for one of their former teammates and friends makes you really question what the fuck this is all about.
Boss sent me a note this morning... for my annual stock option grant. YAY... not really. I just had to watch a fellow dad bury his (only) son and two months ago he lost his wife due to complications of West Nile (no joke... Chicago suburbs). Yay... more options. Whatevs...
When can I stop trading my time for money? That's a great way to think of it. I could have stopped a while ago, I'm sure. But, this I do know. My time, regardless of how much I'm being paid, is FAR better used to spend time with young people, making them better people and lacrosse players than it is building AI and analytic systems as a professional.
Life has thrown too many signals my way for me to justify not living for myself and _giving_ back in ways that I uniquely can.
The end of this chapter should have a G-D fast forward button.