I see where you’re going here but you have the wrong target, CEOs work ridiculously fucking hard, we’re talking 80-100hrs a week. Especially for publicly traded companies — the FCC and general corporate structure makes it basically impossible for them not to be doing ridiculously a lot all the time.
No, the lazy fucks who have more money than god are chairmen and board members. All of the idle involvement, none of the crushing fiduciary responsibility.
Never too late, although it does sound like you could reflect on how much time you spend on you. Your career is great, but you need to be happy first.
Get weird, find some hobbies or just get on some paid (and therefore more serious and less gamey) dating apps and start finding out what you want and what you like. Lack of experience seems like the hardest thing in the world to overcome, but it’s really not, just gotta relax and make some mistakes. Accept that you’re gonna have some awkward interactions and just try to make each of them a fun story…and don’t take pushy advice to heart.