From the ever wonderful Edge.org comes a series of video lectures by Critical Thinking master Danny Kahneman:
I’m deeply ashamed of the rest of the story, but there was something really instructive happening here, because there are two ways of looking at a problem; the inside view and the outside view. The inside view is looking at your problem and trying to estimate what will happen in your problem. The outside view involves making that an instance of something else—of a class. When you then look at the statistics of the class, it is a very different way of thinking about problems. And what’s interesting is that it is a very unnatural way to think about problems, because you have to forget things that you know—and you know everything about what you’re trying to do, your plan and so on—and to look at yourself as a point in the distribution is a very un-natural exercise; people actually hate doing this and resist it.