Ryan Holiday’s Top 7 Reading Tips
#4 Read like you’re having a conversation with the author.
Ryan Holiday is the author of several bestselling books like The Obstacle is The Way, Ego is The Enemy, and Courage is Calling.
His love for reading opened many doors for him. At 22, Ryan worked as a research assistant for Robert Greene — while Greene was writing his New York Times bestseller book, The 50th Law.
At 25, Ryan published his very first book, Trust Me I’m Lying, which debuted in Wall Street Journal’s bestseller list. And in the next 9 years, he has published 11 more books — many of them sold millions of copies.
I admire Ryan. I’ve been reading his books and blog posts for five years now. He inspired me to read more, collect ideas, and share those ideas by writing about them.
After years of following Ryan, I’ve decided to collect his tips about reading.
Here, I present to you the best of them.
1. Read to invest in yourself.
Reading books is how Ryan builds his intellectual assets.
“The decision to make time to read has been the single greatest investment in my life,” says Ryan. “It’s changed my life. It opened up countless doors for me. It made me financially successful. It also helped me manage that financial success and the stresses about success.”
A book can be the greatest investment you’ll ever make.
“Warren Buffet says that the single best investment he ever made was buying a copy of Benjamin Graham’s book, The Intelligent Investor.”
2. Read to access the wisdom from the past.
If you don’t make the time for reading, you fail to take advantage of the wisdom from the past.
“Many people have done whatever it is you’re trying to do,” says Ryan. “In my case of being a writer, being an entrepreneur, people have been doing these for thousands of years. So if I don’t avail myself of their insight, I am stupidly preventing myself from learning from their mistakes.”
It’s also true for other aspects of life.
“How dare you waste your investor’s money by not reading and learning from the mistakes of other entrepreneurs? How dare you take your marriage or your children for granted, thinking that you can afford to figure this out by doing the wrong things first?”
It is wise to learn from your mistakes. It is wiser, however, to learn from the mistakes of others.
3. Read to discover that you’re not alone in your struggles.
“Books are wonderful friends,” writes Ryan.
They can offer you wisdom or healing or companionship — they can give you so much without asking for something in return. They can empathize with your pain. They can remind you, ‘I’ve been there. We’ve all been there. You’ll be fine.’
Ryan quotes James Baldwin:
“You think your pain and your heartbreak are unprecedented in the history of the world. But then you read. It was books that taught me that the things that tormented me most were the very things that connected me with all the people who were alive, or who had ever been alive.”
In Ryan’s words: “You think your pain is so unique — and then you read.”
Read books. You’re not alone.
4. Read like you’re having a conversation with the author.
Highlight lines and passages and quotes. Write your comments on the margins. Argue with the author.
“I mark things that I think are of value to me,” says Ryan. “When I read I fold the pages, I’m using highlighter flags, I’m having a conversation with the author.”
Do not just blindly accept the author’s points. Question them. Argue with them.
Do I believe this? How does this relate to what I know?
“When I meet people who have read my books and they show me all the dog-eared copies, I take that as a praise. You’re supposed to be in an argument, in a discussion with the author.”
5. Take notes.
After Ryan reads a book, he lets it sit for weeks or a month before going back to it again.
Then he captures ideas that resonate with him most using notecards.
He does this longhand because “it helps you create muscle memory. This forces me to go through the material over and over again until it’s locked in my brain. I’ve interacted with the material so many times that I developed a fingertip feel for what it is, what it means, and how I might use it.”
He would then categorize his notes by theme and transfer them inside his commonplace book.
A commonplace book, he said, is like a backup hard drive for your brain.
“I have different sections for all the things that matter to me in my life. I have a section of parenting stuff, I have a section of philosophy stuff, I have stoicism stuff, I have strategy, examples I like from history.”
Start collecting ideas that sing to you. The extra effort to engage with those ideas will make them stick with you more.
6. Engage with your notes.
Ryan believes that engaging with ideas at so many levels helps him engrave them to his identity.
“I love reading more than almost anything, but even I’ll admit that it would be a waste of time if I just let ideas accumulate in my head. More than that, I wouldn’t truly know what I’d read because I’d never put myself out there, applied it, or made connections.”
Ryan sprinkles quotes from the books he’s read into his writing. He collects ideas to create. He reads books to write.
“The Obstacle is the Way began as a single notecard. First I read Meditations, and I read a quote there, ‘The impediment to action advances action, what stands in the way becomes the way’. Then I read Pierre Hadot’s The Inner Citadel, where he talked about turning obstacles upside down. So I went through it, I marked it, turned it into a notecard, and started a new category in my commonplace book.”
First is an idea, then a notecard, then a section, and then a book. It doesn’t always need to end with a book, though.
Yours can be like this:
First is an idea, then a notecard, then a practice, and then a habit.
7. Reread the best books.
Ryan suggests revisiting the books that changed you because you’ve changed since you last read them.
One of the books he loves rereading is Meditations. He said he’s read it a hundreds times.
“It’s the engaging and the re-engaging that taking notes and using them and then applying them allowed me to understand them at a level that just would not be the case if I read it once.”
So instead of asking, “How can I read more books this year?” Ask, “What books can I reread this year?”
Every time you reread a book, you’ll discover new insights, new gems. You missed them before because you’re not yet ready to notice them.
“We never step in the same river twice. For it’s not the same river, and you’re not the same person.” — Marcus Aurelius
Thanks for reading!
