Except that he then goes on to argue that the people who get FU money won't confront those questions because they can't be happy that much money, they'll have to keep going because of their "insatiable hopes of yet greater scores". And, if that's how you think, you're just as trapped as any "wage slave".
(Incidentally, I think the author is wrong, and skewed by his time at Goldman. I personally know substantially more people who have either had "small" payoffs, or have lifestyle businesses or passive income streams, and their desire doesn't seem to be to collect still more money, but rather to spend their time travelling or backpacking or what have you. But, I'm probably just as skewed by living in Portland as the author is from living in Manhattan.)
I think your argument here almost supports his hypothesis though - he argues that there is a correlation between large payouts and a desire to continue and earn even better. So the idea that those people who have smaller payoffs don't still have a burning avaricious desire is consistent with his suggestion.
The question is, /if/ his hypothesis is true and there is a correlation, what is the causation? Does winning big give you a taste for it and make you want to try again? Or is it (more likely in me eyes) that only those with such a strong drive to beat out the odds will ever make it to the really big payouts without cashing in early for less.
(Incidentally, I think the author is wrong, and skewed by his time at Goldman. I personally know substantially more people who have either had "small" payoffs, or have lifestyle businesses or passive income streams, and their desire doesn't seem to be to collect still more money, but rather to spend their time travelling or backpacking or what have you. But, I'm probably just as skewed by living in Portland as the author is from living in Manhattan.)