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Ones I would suggest as gateway drugs would be:

The Code Book, by Simon Singh is a very accessible history of cryptography and its role in historical events.

The Nazi Census, by Aly, Roth and Black, is an important survey of how data collection methods get used for bad things, and I recommend it to anyone doing large scale systems architecture, or working in privacy. (replace statisticians with 'epidemiologists', and you start to see a theme.)

The Mathematical Theory of Communication, by Claude Shannon is beautiful, and gives you an intuition for concepts like bandwith, signal, message entropy, finite fields, among others.

Power, by Jeffery Pfeffer, when combined with the Dictator's Handbook by Smith and DeMesquita forms the foundation for any serious management and strategy consulting.

GEB, by Hofstader was a way to have an intuitive frame of reference about cognitive science and theories of mind, which I think are going to be the next great cultural battle ground, and also relevant in the context of machine learning, and consulting.

My field? Security, privacy, and risk management.



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