enough money to live in one of the most expensive places on earth, probably without having to work too much? check. a family and (apparently) happy marital relationship? check. moderately successful times working at important companies? check.

Sure, it's good to be ambitious and set high goals. But the dude needs to get a grip. If he wants to achieve more, fine. But there's no universal standard by which he's a "failure". At the end of the day it's up to him and he'd do well to admit it.