The Art of War by Sun Tzu - Special Edition by Sun Tzu, translated and annotated by Lionel Giles. Morality aside, this is how you win in war. I prefer this translation to others.
The Prince and Other Writings by Niccolo Machiavelli. Morality aside, this is how you gain power. I like the supplemental material in this particular version.
The Art of War & The Prince by Sun Tzu and Niccolo Machiavelli. Both of the above together in one volume, luckily still with Giles's translation of the Art of War.
Psychology
Psychology - Making Decisions with Intuition
Blink: The Power of Thinking Without Thinking by Malcolm Gladwell An easy read that brings to life lots of research showing that instant decisions made by your unconscious are often remarkably more accurate than slow, detailed analysis. Understanding this phenomenon can be life-changing, once you learn to leverage this kind of mental power.
Strangers to Ourselves: Understanding the Adaptive Unconscious by Timothy Wilson "Know yourself" is a lot easier said than done. This book explains why that is. It shows that our assumption that we have special access to knowing things about ourselves that others can't know is often wrong. It's eye-opening to realize how hard it is to know how we will feel, how will act, and how important (though flawed) our self-stories are.
Gut Feelings: The Intelligence of the Unconscious by Gerg Gigerenzer Similar to and extends the ideas covered in Blink. Reveals some of the tricks intuition uses to get extremely quick answers to complex problems. Provides lots of data an examples from health care diagnoses, prisoners' bail hearings, stock market investments, and other fields showing that the very simple rules intuition uses are more accurate than complex theories in those fields.
Consciousness: An Introduction by Susan Blackmore A 400+ page text book that surveys the confusing field of study surrounding consciousness. Blackmore warns that you will end up more confused when you start because you will realize how little you really know about the subject and realize that many of your assumptions about consciousness are probably wrong...yet the experts all disagree on what is right. She also warns that knowing this much about your own consciousness is disturbing. I can tell you that she's right.
The Power of Intuition How to Use Your Gut Feelings to Make Better Decisions at Work by Gary Klein Exposes the weakness of classical decision theory by showing that experts in every field studied rely on intuition, not complete logical analysis, to make high quality decisions. Intuition takes more data and relationships into account and is more effective than pure analysis at solving highly complex problems.
Psychology - Happiness
Geography of Bliss by Eric Weiner The author visits all the happiest places on Earth (they aren't where you think!) and tries to understand the essence of each country and what makes its people so happy. Before this, he was a foreign correspondent journalist who covered all the least happy places in the world. This writing quality of this book is AMAZING and I highly recommend it for humor/writing alone, not to mention the great content.
Happiness: The Science Behind Your Smile by Daniel Nettle Great science about the evolutionary basis of happiness and the biology behind happiness. Liking and wanting are controlled by separate brain circuits and while that's good for evolution, it's explains a lot of life's heart-aches. Also explains the biological reasons why a positive attitude leads to good health and success.
Stumbling On Happiness by Daniel Gilbert Explains that we are bad at remembering the past as it really happened, therefore we are bad at simulating the future, therefore we are very bad at predicting what will actually make us happy. Good information, but painfully sophomoric and longwinded writing.
Psychology - Mastery
Flow: The Psychology of Optimal Experience by Mihály Csíkszentmihályi Seminal work on the subject of flow, the special state of mind that we experience when we are most productive and when we are pushing the limits of our abilities. Setting up your life to achieve flow more often is the key way to achieve mastery in something and, possibly unexpectedly, has to do with how happy you are in life. Should have been required reading in high school to get everyone on the right path.
Art of Learning: An Inner Journey to Optimal Performance by Josh Waitzkin Waitzkin is a US Chess champion who was the subject of the film Searching For Bobby Fischer. He retired from Chess and took up Tai Chi Chuan, winning several international tournaments in that sport. Wonderful tips about his mindset for accomplishing this amazing feat, but suffers in quality of writing (sorry Josh, I'm still a fan).
Extraordinary Minds by Howard Gardner The study of genius. Compares four types of extraordinary people with an in-depth example of each. The Master (Mozart), The Maker (Freud), The Introspector (Woolf), and The Influencer (Gandhi).
Psychology - Other
Personality Type: An Owner's Manual by Lenore Thomson People have different methods for taking in and processing information. These biological differences lead to different personality types. Your personal life, business life, and your art will benefit from understanding these differences in people.
Emotional Intelligence by Daniel Goleman Like it or not, decision-making is greatly influenced by emotion. IQ seems like it should correlate with career success, but emotional intelligence is actually a better predictor. Positive attitude and emotional intelligence are what separate good competitors from excellent ones. Almost everything we do is affected by our emotional intelligence.
Getting Things Done by David Allen The author doesn't know that this is a psychology book, but it speaks to the wisdom of leveraging your unconscious mind's power by getting all that cluttered daily detail out of its way. Very practical tips for being more productive. Focuses on moment-to-moment behavior that will help, rather than theory or high concept.
The Strategy of Conflict by Thomas Schelling Negotiation power comes from factors you might not expect. This book has application to game theory, but also takes human psychology into account. Has a slant toward explaining negotiations over nuclear warfare and terrorism.
Designing Things
Notes on the Synthesis of Form by Christopher Alexander Required reading for anyone who wants to design anything. Should be called "The Synthesis of Form, Dammit."
The Timeless Way of Building by Christopher Alexander Less technical and more poetic than 'Notes' (above). Alexander tries to describe The Quality Without a Name that makes a design living rather than dead.
The Oregon Experiment by Christopher Alexander Alexander applies the concepts in the previous books to rebuild the Oregon University Campus. Postscript: the undertaking is considered a failure, but not because of Alexander's methods.
How Complex Systems Are Created
The Selfish Gene by Richard Dawkins Our genes don't serve us; we serve them. Understanding the enormous power of genes is applicable to procedural content in games, not to mention how cool it is to have some of life's mysteries explained.
Why I Write (Penguin Great Ideas) by George Orwell Explains four basic motivations of writers and also exposes how politicians use vague language to deliberately deceive.
Ernest Hemingway on Writing by Earnest Hemingway, of course. Few writers were ever so seriously committed to their craft as Hemingway. A valuable glimpse into his mind.
On Writing by Stephen King King was a "20 year, overnight success." Here he explains his hardships, method, and sensibilties.
In these three books, Professor Tufte conveys his strong sensibilities about displaying visual information (such as charts, graphs, and diagrams) in an honest and clear way. I know of no one so forceful and correct on these issues as Tufte:
The Cognitive Style of PowerPoint by Edward Tufte Microsoft Powerpoint presentations lead to simplified, shoddy thinking. This short pamphlet evescerates Powerpoint. You should order a few and leave them around your workplace.
Understanding Comics: The Invisible Art by Scott McCloud This book transcends comics and is actually a manual about displaying visual information in an artistic way. McCloud also investigates what 'art' is and how artists develop.
Richard Feynman, Physicist and Greatest Human
Feynman is the ultimate role model on how to think, learn, and explain.
The Character of Physical Law by Richard Feynman Feynman gives a series of seven lectures on physics intended for lay-people. Equally interesting: 1) learning incredible ideas about how the universe works, 2) seeing how a master of clear explanation explains things, and 3) the many things Feynman says we don't know the answers to yet.
Built to Last: Successful Habits of Visionary Companies by Jim Collins and Jerry Porras My favorite business book. Compares "gold medalist" companies to their 2nd place competitors to determine what the best have in common. This is the product of six years of serious research at Stanford.