First, the title: it refers to the long-held Western belief that “All swans are white.” This was a belief given up in a second once Australia was discovered and a black swan sighted. What the experts had counted upon was untrue and it unsettled ornithology. That anecdote is the whole point of the book: you cannot predict anything with any great degree of accuracy.
Condi Rice’s statement “No one saw it coming” in reference to 9/11 is perhaps the classic remark in illustrating this attitude. And now that 9/11 has happened, it assumes a disproportionate importance in our minds: most of our security measures are devoted to preventing 9/11, while it seems more reasonable to assume that the next terrorist attack will be of a completely different, unforeseen type.
Taleb thinks that most of our world falls into matters of “Extremistan” while we assume it falls into “Mediocristan.” In Extremistan, an extreme occurrence can alter the entire playing field; in Mediocristan, no one occurrence is enough to disrupt everything. Our assumption of Mediocristan is one of the world’s predictability, but few of our wars, our technologies, our tragedies and triumphs were foreseen ahead of time as Taleb amply demonstrates.
What is to be done, according to Taleb, is to assume the world is unpredictable and put yourself out there to take advantage of the randomness that controls the world: go to lots of events, act on the spur of the moment and see what happens.
Taleb’s arguments are essentially a practical, formalized version of David Hume’s arguments against knowledge. Hume used the examples of billiard balls and the sun (why should we count on a billiard ball going into a hole or the sun rising tomorrow just because it’s happened before?). Hume’s arguments are true, but they seem profoundly unhelpful, like a “Yeah, so what? Great, there’s uncertainty in everything. I’ll get over it.” But through a barrage of real-life examples, Taleb ends up convincing us fairly well of his point. My favorite example of his is the turkey story: suppose you’re a turkey who’s been living for a thousand days. Through those thousand days, you might be convinced that you’ll always be fed by humans; humans are great, generous, magnanimous beings. Unfortunately for the turkey, Thanksgiving is coming up; you’re killed on the thousand and first day. Oops.
As far as that goes, Taleb’s advice and arguments are pretty good. But Taleb’s argument is partially polemical and overstates the strength of his argument. He totally denies the usefulness of planning, saying that almost all plans end up failed anyway. But this seems a somewhat strange conclusion to make. We don’t do things just for the hell of it; rather, we must have some idea of what we want, even if we’re following Taleb’s advice. Essentially, what a plan is, is a formalized discussion of what we think we’ll gain and what we think we’ll lose. We shouldn’t owe fealty to the plan, but we should make one; otherwise we’d just be engaging activities because it might help us out, and that makes little sense.
Prose-wise, Taleb carries on as a highly competent polemical writer. He has some very funny anecdotes and examples and is highly readable (a huge plus given the technicality of some of the math examples). On the other hand, his writing can become a bit stale: you’ll tire of the thousandth mention of neckties.
Overall, I highly recommend The Black Swan