These 38 Reading Rules Changed My Life

It’s a weird thing to say, but I guess I’m a professional reader. That’s really what authors are. A book is made of books. “The greatest part of a writer’s time is spent in reading; a man will turn over half a library to make one book,” Samuel Johnson said.

I’ve written 15 books now, which has meant reading many thousands of books in the process. Once a month for the last 15 years, I’ve recommended many of those books in the Reading List Email. And in 2021, I opened my own bookstore filled with my all-time favorites.

So the question I am asked most often is:

How do you read so much? What’s the secret?

The answer is not “I’m a speedreader.” As I’ve written before, speed reading is a scam. The answer is that I have a system, a process that helps me be a productive reader. It’s not my system exactly, as I’ve taken many strategies from history’s greatest readers. Nor is this a system designed around speed or quantity. Reading is wonderful in and of itself, why would I try to rush through it? No, I try to do it well. I try to enjoy it.

In this email, I thought I would detail some of the rules I’ve come to follow over the years. They don’t all make me faster, but they do make me better.

–Do it all the time. Bring a book with you everywhere. I’ve read at the Grammy’s and in the moments before going under for a surgery. I’ve read on planes and beaches, in cars and in cars while I waited for a tow truck. You take the pockets of time you can get.

–Physical books only.

-It’s not that I have a problem with audiobooks–if it gets you reading, I’m all for it. I just think there’s something very special about the physical form. I just read a great book about this actually called Proust and the Squid by Maryanne Wolf.

–Hardcover over paperback.

–Bring a pen with you too. Reading is better if you’re taking notes.

–Keep a commonplace book. As Seneca wrote: “We should hunt out the helpful pieces of teaching and the spirited and noble-minded sayings which are capable of immediate practical application—not far far-fetched or archaic expressions or extravagant metaphors and figures of speech—and learn them so well that words become works.” (Here’s a video on my commonplace book method).

–Err on the side of age. Classics are classics for a reason.

-Beat them up. Books are not precious things. As an author, I love it when people hand me a book to sign that has had real miles put on it. When people hand me a pristine copy and tell me it’s their favorite, I assume they are just flattering me. It’s obvious what my favorite books are…because they’re falling apart (here’s my copy of Meditations for instance).

–In every book you read, try to find your next one in its footnotes or bibliography. This is how you build a knowledge base in a subject—it’s how you trace a subject back to its core.

-Same goes when you find an author you love, read them ALL. I read Cecil Woodham-Smith’s book on the charge of the Light Brigade…only to find she had also written a biography of Florence Nightingale. It was that discovery that shaped a full third of my book Courage is Calling.

-That comment from (the disgraced and indicted FTX founder) Sam Bankman Fried about how every book could be a 900 word blog post is preposterously stupid. The whole point of reading is to really understand something. So if all you’re after is the ‘gist,’ skip books and stick with blog posts.

–If you see a book you want, just buy it. Don’t worry about the price. Reading is not a luxury. It’s not something you splurge on. It’s a necessity. Even if all you get is one life-changing idea from a book, that’s still a pretty good ROI.

-That might sound privileged, but Warren Buffett considers the foundation of his multi-billion dollar empire to be a book. At 19-years-old, he bought a copy of The Intelligent Investor by Benjamin Graham. We don’t know exactly what he paid for it, but in the early 1950s, a hardcover typically went for $1.30–the best investment he ever made, he’s said. Today, Buffett’s worth $108.7 billion, having given away some $37 billion to charitable causes. Not a bad ROI!

–Some people might recoil at categorizing a book that way, but as a lover of literature, I have no problem with it. I myself wouldn’t be writing this to you today if I hadn’t bought a paperback of Meditations in 2006 for $8.25 on Amazon. That book of philosophy taught me not just about life, but also schooled me in the art of writing, in working with and managing people, and gave me the speciality which I now write my own books about. Again, not a bad ROI.

–Don’t just read books, re-read books. There’s a great line the Stoics loved—that we never step in the same river twice. The books don’t change, but you do.

–As I said, speed reading is a scam. You just have to spend a lot of time reading.

–If a book sucks, stop reading it. The best readers actually quit a lot of books. Life is too short to read books you don’t enjoy reading.

–The rule I like is ‘one hundred pages minus your age.’ Say you’re 30 years old—if a book hasn’t captivated you by page 70, stop reading it. So as you age, you have less time to endure crap.

-Embrace serendipity. So many of my favorite books are just random things I grabbed at bookstores (this is why I say don’t sweat buying a book–just roll the dice). That’s what bookstores are for, what I’ve tried to build mine around. It’s a discovery engine better than any algorithm.

-Don’t just build a library, build an anti-library—a stack of unread books that humbles you and reminds you just how much there is still to learn. It’s a sign of what you don’t yet know. It’s also a resource there whenever you might need to do a deep dive into that topic.

–Emerson’s line was, “If we encounter a man of rare intellect, we should ask him what books he reads.” When I was a teenager, I got in the habit of doing this. Every time I would meet a successful or important person I admire, 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).

–Speaking of Emerson…in his essay “Reading,” he put down his three rules: “1. Never read a book that is not a year old [because only good books survive]. 2. Never read any but famed books [same reason]. 3. Never read any but what you like.”

–Whenever I’m in a reading funk/dry spell (most commonly, around book launches), I find I’m able to get back into a groove by re-reading some of my favorite novels. What Makes Sammy Run? The Great Gatsby. Ask the Dust. The Moviegoer.

-Speaking of Ask the Dust, I read that because my friend Neil Strauss said in an interview it was his all-time favorite novel. He also turned me onto Knut Hamsun’s Hunger, which he had also raved about. When people rave about something, don’t dismiss it. If someone says a book changed their life? Consider it seriously. They’re talking about something powerful.

-I find myself sometimes reluctant to read something that’s super popular. That snobbishness never serves me well. More often than not, when I get around to those bestsellers I kick myself–they were bestsellers for a reason! They’re great! Don’t be a book snob.

You say you don’t have time to read but what does the screen time app on your phone say? What does your calendar say?

–If you want to understand current events, don’t rely on breaking news. Find a book about a similar event in the past. Read history. Read psychology. Read biographies. Go for information that has a long half-life, not something that’s going to be contradicted in the next bulletin.

-Examples: Read The Great Influenza to understand COVID. Read It Can’t Happen Here to understand modern threats to democracy. Read First Principles to understand American politics.

–Ruin the ending. I almost always go straight to Wikipedia and figure out the plot–especially if I am reading something tough like Shakespeare or Aeschylus. Who cares about spoilers? Your aim as a reader is to understand WHY something happened, the what is secondary.

–One of the things that people in publishing know is that readers tend to skip prefaces and forewords. This is crazy! Those things are there for a reason. They often have a ton of helpful and interesting stuff about the context around when the person was writing, who the work ended up influencing, and other tidbits that sometimes stick with you longer than even the work itself.

-”Don’t be satisfied just getting the ‘gist’ of things,” is what Marcus Aurelius learned from his philosophy teacher Rusticus. One of the reasons I try to spoil the plot, make my way through the intro and the preface, read reviews and articles about the books I’m reading, watch videos about them, and read other books on the topic is because I want to really understand what I’m dealing with. If I don’t, if I only want a surface take, why read a book at all?

–When intelligent people read, they ask themselves a simple question: What do I plan to do with this information?

-My favorite line from Harry Truman is, “not all readers are leaders, but all leaders are readers.” When we read, we aren’t learning to impress people, to win some game of mental gymnastics. It’s to get better, to find things you can use in your real life. If you’re looking to expand what you do with the books you’re reading, I highly recommend our Read to Lead course. It’s been taken by over 10,000 people, and is our most popular for a reason.

Read widely and from people you disagree with. The Stoics believed that we should actively engage with anyone who can be a source of wisdom to us, regardless of their origin. If there is wisdom out there to be had, we’d be wise to avail ourselves of it.

-Pretentiousness is bullshit. Epictetus once heard a student talking proudly about having made their way through the dense works of Chryssipus. You know, Epictetus told him, if Chryssipus had been a better writer, you’d have less to brag about.

–Look for wisdom, not facts. We’re not reading to just find random pieces of information. What’s the point of that? We’re reading to accumulate a mass of true wisdom—that you can turn to and apply in your actual life.

-Another line from Seneca is about how people get too caught up in the facts and figures and they miss the message. I totally agree. On the literary snobs who speculate for hours about whether The Iliad or The Odyssey was written first, or who the real author was (a debate that rages on today), he said, “Far too many good brains have been afflicted by the pointless enthusiasm for useless knowledge.”

–If a book is good, recommend it and pass it along to other people.

It’s the last one that I follow the most. I’m proud of the books I’ve been able to champion and turn people onto over the years. I feel like I am paying forward what the Gregory Hays translation of Meditations did for me (I loved it so much I put out my own edition you can grab here).

I love looking around my bookstore and seeing titles that I don’t see in other bookstores very often. Just recently, Ann Roe’s publisher of Pontius Pilate told us they had to do another printing because we’d raved about it too much. I heard something similar about William Seabrook’s Asylum. That’s the job of a reader and a writer–to find great stuff and suck everything you can out of it as you read it and re-read it.

And to help others do the same.

I hope these rules help you help yourself and help others.

Written by Ryan Holiday