Drive: The Surprising Truth About What Motivates Us -- Dan Pink (http://www.amazon.com/Drive-Surprising-Truth-About-Motivates...)
Linchpin: Are You Indispensable? -- Seth Godin (http://www.amazon.com/Linchpin-Are-Indispensable-Seth-Godin/...)
The Laws of Simplicity -- John Maeda (http://www.amazon.com/Laws-Simplicity-Design-Technology-Busi...)
Zen and the Art of Motorcycle Maintenance -- Robert M. Persig (http://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry...)
Invisible Man -- Ralph Ellison (http://www.amazon.com/Invisible-Man-Ralph-Ellison/dp/0679732...)
How to Win Friends and Influence People -- Dale Carnegie (http://www.amazon.com/How-Win-Friends-Influence-People/dp/06...)
The Kindle app has really got me buying a lot of books that I now need to finish...
- Simple Heuristics That Make Use Smart by Gigerenzer, et al. (http://www.amazon.com/Simple-Heuristics-That-Make-Smart/dp/0...). I have heard good things about this book but have not read it yet.
Category 2:
- Think Twice by Mauboussin (http://www.amazon.com/Think-Twice-Harnessing-Power-Counterin...)
- Influence by Cialdini (http://www.amazon.com/Influence-Psychology-Persuasion-Busine...)
Category 3:
- You already mentioned Michalko, but his other book, Thinkertoys, is also very good (http://www.amazon.com/Thinkertoys-Handbook-Creative-Thinking...)
Category 5:
- Switch by the Heath brothers is excellent (http://www.amazon.com/Switch-Change-Things-When-Hard/dp/0385...)