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.
Collapse: How Societies Choose to Fail or Succeed by Jared Diamond
Subject: What causes civilizations to collapse, and how to prevent it.
Lessons: Collapse is usually caused by a civilization exhausting its natural resources. Examples include Easter Island, Norse Greenland, and modern Rwanda. There's more, but it's my father's book, and not mine.
I didn't like this book. The whole book focuses on societies that are obviously very different from our own - orders of magnitude smaller, and having no scientific understanding of their world. Then it attempts to carry lessons over.