A book I’ve heard about for at least a decade, but only now got down to reading after my Kindle broke and I decided to get into my many many unread paper books. It’s a great read, albeit one best taken in small doses; you certainly could read the whole thing in a few afternoons but it’s better to read a few pages then think, I think.
Taleb’s central point seems to be that our humanly-devised models of reality cannot predict everything, and we can’t even determine the limits of our competence; so we don’t know what we can’t predict – at the best, we can assume there are things we can’t predict, which stand on the margins of our science like sea serpents drawn on maps – here be dragons, Hic sunt dracones on the Hunt-Lenox globe.
It is therefore imprudent to build systems which will fail too heavily upon contact with the unexpected.
Taleb’s style is not for everyone. He leads to philosophical points through personal anecdotes, usually about unshaven, hairy-handed working men from the 2nd or 3rd-world who can barely read but are smarter than all the Harvard PhDs; there are several anecdotes about Taleb at conferences where he outrages academics with his blunt manner & wisdom. I don’t really mind the near-constant sense of Taleb’s ego, as he has the ballsiness, achievement, and intellect to justify a certain self-satisfaction; I merely withdraw from his worldliness, his lack of a spiritual dimension. He’s an exemplar of Rene Guenon’s Reign of Quantity, a man who sees everything in quantitative terms; thus missing the element of Fate.
There is nonetheless a great deal to enjoy, many passages I marked, e.g. :
In real life you do not know the odds; you need to discover them, and the sources of uncertainty are not defined.
and
The notion of future mixed with chance, not a deterministic extension of your perception of the past, is a mental operation that our mind cannot perform.
and
Likewise, do not try to predict precise Black Swans – it tends to make you more vulnerable to the ones you did not predict.
Taleb’s worldview is alien to my own; he’s one of these rootless cosmopolitans who lives in major cities – could live nowhere else – even as he talks about his ancestral hometown as the source of his wisdom and clarity. He would probably regard anyone who prefers to be rooted among his folk as a provincial loser and a racist, as if for all his intelligence he cannot quite bear to scrutinise the magic R word (or he doesn’t want to forfeit his conferences and interview requests and literary celebrity).

There is a slight sense of emptiness about his great intellect and learning – I want to ask, what is all this for? why be so smart? just to make more money? But that’s also testament to his greatness – were he a mediocre pop-science writer, the question would not arise.
