Rather than the outcome itself, it is how the outcome was achieved and to what extent is governed by randomness or lack of it that is of prime importance.
As Taleb mentioned in Fooled by Randomness, a janior winning a lotter ticket for a million, and a dentist who earns the same after three decades of practice can afford to buy a house of equal value. However, if the janitor was to relive his life a million times, only one out of the million lives he's lived would have earned him a million bucks. The rest of the lives, he would be wasting his money on countless lottery tickets, thus averaging his payoff to zero.
Whereas the range of dispersion for the dentist is far smaller.
As Taleb mentioned in Fooled by Randomness, a janior winning a lotter ticket for a million, and a dentist who earns the same after three decades of practice can afford to buy a house of equal value. However, if the janitor was to relive his life a million times, only one out of the million lives he's lived would have earned him a million bucks. The rest of the lives, he would be wasting his money on countless lottery tickets, thus averaging his payoff to zero.
Whereas the range of dispersion for the dentist is far smaller.
BTW, Taleb himself kept buying truck loads of lottery tickets (Options) waiting for the Black Swan to show its face. Ultimately, the fund had to be closed and Black Swan came but in India and not in the US.
Regards,
--Ashish