Less Wrong is a community blog devoted to refining the art of human rationality. Please visit our About page for more information.
Followup to: Unteachable Excellence
As previously observed, extraordinary successes tend to be considered extraordinary precisely because it is hard to teach (relative to the then-current level of understanding and systematization). On the other hand, famous failures are much more likely to contain lessons on what to avoid next time.
Books about epic screwups have constituted some of my more enlightening reading. Do you have any such books to recommend?
Please break up multiple recommendations into multiple comments, one book per comment, so they can be voted on and discussed separately. And please say at least a little about the book's subject and what sort of lesson you learned from it.