A while back I read the The Black Swan. I could have sworn I reviewed it, but I can't seem to find it. Given that it's been out for a while now, and plenty of quality reviews are available (better than I could have produced) I probably won't be rectifying that situation. Here a link worth checking out that I picked up recently from a DL I'm still on.
And this one from Everything2, a community I've just joined that looks promising.
If you like to listen, I found this podcast, done by EconTalk, covered many of the key points that are detailed in the book.
It's relevant to me at the moment because I'm engaged in a planning exercise. The traditional means of pursuing that activity, and of executing, treats the world as if "Mediocristan" was the only game in town. And of course, not only is it not the only game, in this case it's most definitely the wrong game. Additionally, Taleb makes explicit his views about the primacy of confirmation bias. He's not afraid of saying scary, and counter intuitive things -- things like "the more information you consume, the less you know". Confirmation bias, incidentally, is behind that observation. Nevertheless, planning must be done, and Taleb does provide some interesting thoughts on that score. Personally, I've adapted his "dumbbell" approach to several different planning problems I face.
Mediocristan, Extremistan, "dumbbell" approach? You'll just have to read the book.