I just finished reading The Black Swan: The Impact of the Highly Improbable. It is, as Kevin Drum notes, an odd book to read. The tone makes you want to not trust Taleb, and he almost tells you not to trust him, but then his ideas make some sense. He seems prescient about the current financial crisis, as his whole book suggests that financial institutions are generally blind to outlier events such as the mortgage bubble and ensuing stock market crash because they use models based on the bell curve rather than a power law. His argument is basically that black swan events, those that no one predicted, happen more often than we think, and that our models of prediction are terrible at predicting even smaller versions of these events, much less the seriously catastrophic (or conversely, seriously beneficial) ones.
Taleb has equal scorn for academics and bankers. Academics are too insular, having never been in "real" decision-making situations. Bankers are in real decision-making situations but don't think critically about those decisions. They check their brains at the door. Worse for him are bankers who use tight mathematical models from academics to predict risk.
Interestingly, when searching the blogosphere to find what others have said about the book, I mostly found commentary on Taleb's hedge fund that is based on his ideas. Some have claimed it's not doing well--because his strategy is to lose small amounts of money 90% of the time and win big 10% of the time--while others have touted its brilliance. I don't care much about applying his ideas to finance, even though that's his field. I think it's more interesting to consider the idea of the black swan, both positive and negative in more general terms. He says to be open to opportunity, to be generally open-minded about what might happen. Try as much as possible to think outside the box. People are not predictable; society as a whole is even less predictable.
I remember being a kid trying to imagine how my life would turn out--what kind of job would have, who would I marry, would I have kids, where would I live--and it always felt like this black hole. I was not, back then, one of those people who planned much past the next few days. I had friends who were already planning to be doctors or lawyers and were planning their classes and colleges based on those plans. I just figured some unexpected event might occur that could change any plan I made. I was right. Just thinking that something unexpected might occur helps you deal with it. It doesn't mean that when a good thing or a bad thing happens that it doesn't impact you. It just means that you can take it in stride. You can just start doing what you need to do to minimize the pain or take advantage of the opportunity. Rather than, as I sometimes do now, worrry about what might happen, and conjure up all the most horrible images, it makes more sense to live from day to day. It's harder than you think.