michaelmilton comments on Great Books of Failure - Less Wrong
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To Engineer Is Human: The Role of Failure in Successful Design, by Henry Petroski
Summary: Petroski takes us through a bunch of conspicuous engineering failures throughout history and describes the technical and sociological solutions that followed.
Lessons: Engineering runs through alternating cycles in history where periods of innovation, new ideas/materials, and speed result in disasters (the Tacoma Narrows bridge), followed by periods of conservatism and overbuilding (the Firth of Forth).
I think the best cautionary tale in this book is the 1981 collapse of the skywalk in the Hyatt Regency in Kansas City from what was thought an extremely minor design change. In any event, the book addresses lots of failures and is well-written and readable.