Books that changed my life

For someone that reads books for a living, I’m pretty lazy about updating my recommended reading list. After two years of leaving it untouched, I’ve finally updated it.

Here it is, reproduced below.

Source
I don’t understand it when someone says, “I read books, but a book has never changed how I see the world.” Books are constantly changing my understanding of myself and how the world works.

Here, I share a list of the books that have had the biggest impact on me.

Highly Influential
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.
Still Pretty Damn Good
The books here are still pretty damn good and worth recommending, but they are not life-changing like the books above.

Liberty by Isaiah Berlin. Berlin’s ideas of value incommensurability & incompatibility have helped alleviate what, in my early twenties, was an obsessive desire for the ‘perfect’ life. I was so used to thinking of terms of “best answer” and “optimization” that it took a long time to just grasp what (despite his clear writing) the guy was talking about.
The Monk and the Philosopher by Ricard & Revel. A conversation between a molecular-biologist-turned-Buddhist-monk and his father, a prominent French intellectual. The West has a particular (and often problematic) way of seeing the world, but it’s hard for someone inside the system to see it from the outside.
The Case Against Education by Bryan Caplan. A compelling case that a lot of education — especially higher education — doesn’t teach many valuable skills. It’s more of a big IQ and personality test.
How to Worry Less About Money by John Armstrong. Armstrong points out something that (in retrospect) is incredibly obvious — many money problems aren’t actually about money at all. They’re about how we think about money. Which, in turn, means that you can’t solve them by earning more or spending less.
Letters from a Stoic by Seneca. One of the first books of non-fiction I ever read. I still turn to it when life starts going wrong.
The Complete Essays by Michel de Montaigne. The father of the modern essay. Honest and inquisitive, he seems to cover every aspect of human nature in his wandering writings, but he always comes back to one core lesson: be skeptical — think for yourself.
Spent: Sex, Evolution and Consumer Behavior by Geoffrey Miller. A thought-provoking book that connects consumerism and evolutionary psychology. Gave me a new set of ways to think about our obsessive consumerism. We often buy things not for their uses, but for what those things tell others about us.
Status Anxiety by Alain de Botton. This book did a lot of cognitive heavy lifting for me by clarifying the connection between anxiety and our hyper-competitive culture. (A close second to this book is de Botton’s The Consolations of Philosophy.)
Gut Feelings: The Intelligence of the Unconscious by Gerd Gigerenzer. Definitely read this if you are a fan of Dan Kahneman’s Thinking, Fast and Slow. Kahneman tends to study heuristics/and intuition with the question “When does intuition fail?” Gigerenzer takes the opposite starting point, asking, “When does intuition succeed?”
Seeing Like a State by James Scott. I’m a fan of the blog Ribbonfarm, which is named borrowed its name from this book. Some brain-turning examples of how ideas in our heads take on shapes in the physical world.
Being Wrong by Kathryn Schulz. I think this book would have made my “highly influential” list if I’d found it five years earlier. By the time I read this, I was already familiar with the main ideas, so it ended up being a refresher more than anything.
How to Think by Alan Jacobs. A short read that challenged my beliefs on critical thinking as a solitary, non-social activity.
The Blank Slate: The Modern Denial of Human Nature by Steven Pinker. It’s terrifying how you can come out of 16 years of education and have absolutely no clue how big of a role biology plays in who you are. I was blaming my parents for all sorts of things that they had nothing to do with! This book was a much needed cure for a hurtful and limiting set of ideas that a lot of us grow up with. It’s also got me interested in evolutionary psychology, cognitive psychology, linguistics, and all the other sciences that help us learn about human nature.
Me, Myself and Us by Brian Little. A great introduction to personality psychology that isn’t overly pop science-y. Helped me outgrow the narrative-driven thinking about psychology that we grow up with.
I’ve left out some more practical, self-helpy books from this list. Maybe I’ll add them in another time if people want to see them.