The Incerto Series by Nassim Nicolas Taleb
The Incerto Series is a series of 5-volume philosophical essays on uncertainty written by Nicholas Nassim Taleb. He introduces a contrarian view of approaching finance specially dealing with outliers, extremeness, and explaining things after the fact. These essays are refreshingly original. They do get repetitive at times, but the points conveyed are worth remembering. The first two titles in the series, Fooled by Randomness and Black Swan, have gained a lot of popularity, but the other three (Anti-Fragile, The Bed Of Procrustes, Skin in the Game) also have some interesting ideas.
I loved Black Swan for some of its unique perspectives. A black swan is a highly improbable event with three principal characteristics: it is unpredictable, it carries a massive impact, and, after the fact, we concoct an explanation that makes it appear less random and more predictable than it was.
Taleb has valid criticism of the financial industry’s reliance on models that fail to account for the true nature of uncertainty and the potential for catastrophic events. His discussion of the “antifragile” concept that argues that some systems are strengthened by encounters with disorder is a very powerful concept; I have found it useful in quantitative trading.