These books have had the biggest impact on how I think about, see, and act in the world.
- Incerto by Nassim Taleb. A couple times a month, I get an email or message asking, “Why do you like Nassim’s books? He’s an arrogant asshole!” Well, I actually kind of like arrogant assholes. But, more importantly, Nassim’s books opened up more new ways of seeing & thinking about things for me than, arguably, all the other books in this list added together. I revisit his books now, 5+ years later, and I’m still learning new things. Note: The Incerto is actually a bundle of four books — Fooled by Randomness, The Black Swan, Antifragile, and The Bed of Procrustes.
- The Righteous Mind: Why Good People Are Divided by Politics and Religion by Jonathan Haidt. You’re seriously mistaken if you think politics is driven by careful, rational thinking. We vote emotionally, and emotions tied to morality are some of the most powerful (and violent) ones. What Haidt does so well is ground these moral emotions in evolutionary psychology & anthropology and then show us how differences can affect our moral, political and religious view of the world.
- Superforecasting: The Art and Science of Prediction by Philip Tetlock & Dan Gardner. Tetlock managed to destroy my trust in expert judgment (“No better than chimpanzees throwing darts, really?!”) and then restore it again (“Political forecasters suck, but you can learn to do better!”) — all in a single book. (I’d also check out Tetlock’s Expert Political Judgment: How Good Is It? How Can We Know?.)
- Straw Dogs: Thoughts on Humans and Other Animals by John Gray.Reading Gray’s books sort of feels like getting dumped by your high school sweetheart. It’s incredibly depressing, but you’re a lot better off for it in the long run. (You might like this if you liked Harari’s Sapiens).
- The Use of Knowledge in Society by Friedrich Hayek. Not really a book, but whatever. Print it out, read it, scribble notes all over this. You can love or hate Hayek, but everyone should be exposed his ideas. It was life-changing for me to realize that complex systems can work without anyone understanding how or why they do so.
- Happiness by Design: Finding Pleasure and Purpose in Everyday Life by Paul Dolan. This gave substance to a lot of the nagging doubts I’ve had about happiness research. Most happiness studies use self-reporting, and self-reporters often have no clue what they’re talking about. Plus, the stories we tell ourselves often “override” our actual feelings, sometimes making us say, “It was a good life” or something when we were actually miserable the whole time. (Which, by the way, is why I’m skeptical about listening to the regrets of the dying as a guide for how to live your life.)
- What Do You Care What Other People Think? by Richard Feynman. A curious and playful physicist, womanizer and adventurous safe-cracker, Feynman had absolutely no respect for false authority. Did I mention he won the Nobel Prize in physics? Feynman had a big impact on my writing style, and he taught me to write clearly, use intuition, and always, always think for yourself.