By the rules of your game, a driven executive who makes hundreds of millions of dollars but can't find real satisfaction is more "objectively winning" than a guy who's straddling the poverty line but has everything he needs and is very happy with his life. You don't even realize that the second guy isn't playing the same game. You're playing Monopoly, leaning over to the guy playing checkers across the way, and screeching that he's a loser because he doesn't have any hotels.