Part of the problem is that you only get one real crack at the career game. As you get older, your options diminish and the negative social inferences that come with age (even though they have no basis) tend to mount, so you don't have a lot of chances.

Bosses definitely pick their successors based on the "one of us" metric, much more than actual merit or job performance, and this usually means one has to live in the same expensive neighborhoods and send one's kids to the same expensive schools as theirs. Is it possible to succeed, without playing that game? Yes, of course. However, it's unlikely, and so I wouldn't bet my life on it.

I guess I've never seen any of that but maybe I just don't travel in those circles.