Some of these have been mentioned, but these stand out for me Programming: Getting Real The Pragmatic Programmer Hackers and Painters Business: Good to Great Start Your Own Business (I knew basically nothing about small business before I started, and it's a good intro) Crossing the Chasm (good so far, haven't finished) Technology/Culture: The Long Tail The World is Flat Productivity/People: Getting Things Done Getting to Yes How to Win Friends and Influence People
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