The Black Swan is pretty long (15 hrs) and has some big stretches that aren't that useful (the first hour or two & 3 more hrs toward the end). Nassim Nicholas Taleb is an almost-insufferable narcissist (if I heard one more reference to his Wharton degree and/or hometown in Lebanon I think I would lose my mind). But I have to say, after all that, this was possibly the very best non-fiction, non-economics book I've ever read in my life. I'm not sure if I know anyone who will not be bored to tears with this book. But if you happen to be, as I admit that I am, someone who thinks constantly about epistemology and is always searching for better frameworks for understanding the world around us, I've never seen a more purely useful, practical non-economics book.
Assuming you've already read Sowell / Landsburg / Harford / R. Frank and are well on your way to mastering the basics of practical, everyday, applied "thinking like an economist," and you have time to move onto other things then I'd say this guy Taleb has a lot of extremely useful things to say. And when I say a lot, I mean a LOT.Incidentally, the Black Swan concept is not the theme of the book. It's just one illustration of his real core idea. The Black Swan is the idea that, contrary to overwhelming conventional wisdom, the universe is almost never Gaussian, and the fallacy of the bell-shaped curve leads us to drastically underestimate the expected frequency of extra-ordinary events. But his real point is more basic than that. When you distill the book down, he is essentially saying that it's human nature to simplify everything we see and learn into stylized, Plato-nified models, and that always, always leads us to misunderstand the world and everything in it.
Taleb is obviously an undergrad-philosophy-major-turned-Wharton-MBA-quant jock-PhD-who-grew-up-speaking-French-in-an-elite-Beirut-family-before-coming-to-the-U.S.-and-spends-a-lot-of-time-in-Europe. (Make your own judgments.) : ) But if you can get past all that, the book was truly amazing. I'm glad I did. And I expect I'll have to re-listen to it a few times to make sure I got it all. It really was worth it.