This Question Will Change Your (Reading) Life

When I was a teenager, I began a habit that would change the course of my entire life. I don’t mean to overstate it — it was simple, just a question I would ask the people I met — but without it, I’m not sure who I would have turned out to be.

Every time I would meet a successful or important person I admired, I would ask them: What’s a book that changed your life?* And then I would read that book. (In college, for instance, I was lucky enough to meet Dr. Drew, who was the one who turned me on to Stoicism.)

Who I asked the question to first, or how I came to the habit, I can’t recall, but the results stayed with me. I can reel off the titles of the books that came out of it like they are tattooed on my body:

• 48 Laws of Power
• Meditations
• Autobiography of Malcolm X
• History of the Peloponnesian War
• What Makes Sammy Run?
• Man’s Search for Meaning

The question that produced these books as answers was not borne of idle curiosity. It was my way of cutting through a personal conundrum, which was this:

I loved books and was very hungry for the good stuff — what Tyler Cowen has called “quake books.” The ones that shake you. That knock everything over and turn it upside down. But I also understood that there are so many books out there, and only so much time. It was overwhelming.

Which books should I read? Should I read books about physics or books about history or books about self-improvement? And even if I knew the genre I preferred, which authors should I read and why? Should I read new books or old books? The books getting rave reviews or the classics or the ones on the featured table in the front of the store?

I didn’t know. So this question was my hack.

If a book changed someone’s life — whatever the topic or style — it was probably worth the investment. If it changed them, I thought, it might at least help me.

What resulted was a kind of ad-hoc reading list of transformational books and surprise rabbit holes that I would have never expected. Because the books that change people cut across the entire spectrum of intellectual pursuits: philosophy, psychology, literature, poetry, and self-help. The discrete topics of those books, individually, are as varied as the individuals who answered this question.

You could fill up an entire life of reading with just these books and that would be enough.

Literature is the accumulation of painful lessons humans have learned by trial and error.

Eventually, I applied this little trick beyond just people that I met. Whenever I read interviews of interesting people and they mentioned a book that was particularly influential or important to their development, I would buy it.

I didn’t need to be told in person. I didn’t even need to be the one asking the question. (The New York Times By The Book column is a good place to start)

I read an interview where Neil Strauss mentioned John Fante’s Ask the Dust, so I bought it, read it, and fell in love with it… and in reading about John Fante, I learned that he’d been influenced by Nietzsche and Knut Hamsun, so I read both of them. Napoleon and Alexander Hamilton were changed by Plutarch’s Lives (and so were about a million other people across history), so of course, I read it. I heard that Phil Jackson recommended his players read Corelli’s Mandolin, and that Pete Carroll recommends The Inner Game of Tennis. Lots of successful people have reading lists that they either post on their blogs or that their biographers have compiled after their deaths. I made my way through those, too, book by book.

This strategy has led me to some busts, of course. Elon Musk supposedly loves Twelve Against the Gods, but I didn’t quite get what the fuss was about (the used copy I bought cost $139). Entrepreneurs I admired swore by Ayn Rand so I read Atlas Shrugged, but even in my early twenties, I thought it was a bit ridiculous. Tim Ferriss loves Zorba the Greek, but it didn’t do it for me. But even in these books, I got something out of them. I got more out of them than I would have from most of the forgettable titles the New York Times was slating for review or whatever was tearing up the bestseller lists at the moment.

Socrates supposedly said that we should employ our time improving ourselves by other men’s writings, and that in doing so we can “come by easily what others have labored hard for.” Yes. That’s the point of literature — it is the accumulation of the painful lessons humans have learned by trial and error. For 5,000 years we’ve been recording this knowledge in books. The more hard knocks we can avoid by reading them, the better. (This quote, attributed to Mark Twain, says it well: “The man who does not read good books has no advantage over the man who can’t read them.”)

Not only have we been creating books for thousands of years, but humans — particularly the smart and successful ones — have been reading them for just as long. We’ve been reading on cuneiform tablets, on scrolls, on books created out of stretched animal skins, and now on mass-produced paperbacks and via Audible. Over those centuries, there has been an incredible filtering mechanism working for us, finding and highlighting the books that contain the most wisdom.

That’s why I started asking people for the books that changed their lives. We should seek out the literature that has shaped the people we admire and respect — we can cut down even on the discovery costs of looking for those books. They’ve given us a shortcut to the treasure map.

Everybody seems to want a mentor. Meanwhile, they’re passing up the opportunity to learn directly from the people who taught the people you aspire to be. When someone like John McCain spends his whole life raving about For Whom The Bell Tolls, why would you not check it out? Clearly, it got him through some shit. Peter Thiel credits Rene Girard and Things Hidden Since the Foundation Of the World with shaping his worldview. Clearly, it’s made him some money — you’re not going to pick that up? Angela Merkel — Forbes’ number one most powerful women for 12 of the last 13 years — lists Leo Tolstoy’s Anna Karenina and Fyodor Dostoyevsky’s The Brothers Karamazov as her favorite reads. Add them to the list!

We’re trying to filter the good stuff to the top — to upvote it — to make it even more readily available than it was in our own lives.

Every person you admire has influences. They didn’t come out of the womb the way they are now, and it wasn’t only lived experience that contributed to what they know or how they think. Right now, I am reading How The Classics Made Shakespeare… which is literally a book about all the books that taught the greatest playwright who ever lived.

Why not try to find these books? You’re just going to figure it all out on your own? You’re going to just pass on this opportunity for connection? (I’ll tell you, there is nothing people like hearing more than thoughtful questions about their favorite book or author.)

C’mon.

Send an email. Raise your hand and ask a question. Stop by office hours. Dig through old interviews.

Then…

Go to the library. Pull up Amazon and buy the cheapest used copy you can find. “Borrow it” from a friend.

Whatever it takes.

And after these books change you, as wells as other books you discover on your own, you have one important job: You have to pay it forward.

Because that’s what we’re trying to do here — we’re trying to help others learn from the wisdom of other’s experiences. We’re trying to filter the good stuff to the top — to upvote it — to make it even more readily available than it was in our own lives.

That’s why I keep my own list now, of books to base your life on. It’s why I run my reading list newsletter each month. And it’s why I’ll almost always stop, no matter how tired I am or how many emails I have in my inbox, to respond when people ask: What books changed your life? What do you think I should read?

Because it’s the most important question in the world.