
August Fruge, longtime director of the University of California Press, wrote an excellent memoir, A Skeptic Among Scholars. There are many academic novels and memoirs, but I think very well of Alvin Kernan's In Plato's Cave. Also there is Herbert Simon's Models of My Life, which touches on academia and computing.
Peopleware by DeMarco The Psychology of Computer Programming, Secrets of Consulting, and Becoming a Technical Expert by Gerald Weinberg. Not exactly fitting into the category, but worth reading if you can find it: Models of My Life by Herbert Simon.
A co-worker who left to become a consultant took the Weinberg books along with him.
- "Poor Charlie's Almanack" by Charlie Munger
