His one advantage
He might hate people reading over his shoulder on the train, but at least he has some positive points as well.
For one, he lives in a continual state of pseudo mid-life crises. Growing up with constant reminders about how intelligent and special and remarkable he is, he persistently believes that he’s under performing, that he has not yet achieved enough, that he could be doing so much more.
One of his saving graces is that he doesn’t equate success with money, as a lot of his peers do. Well, as a lot of his peers did. He removed himself from that environment to one where there are more important measures of success.
Would he ever be successful enough? The question burns him, and would probably always be answered with a concrete and rigid ‘No!’
You can’t win if there are no goal post except for the ever-receding horizon.