Read To Lead: How To Digest Books Above Your “Level”
People always ask me if the books I carry around are for school because they’re full of notes, flags and folded pages–why would anyone work so hard on something they were doing on their own? Because I enjoy it, because it’s the only thing that separates me from ignorance.
By 
Ryan Holiday
The best advice I’ve ever got about reading came from a secretive movie producer and talent manager who’d sold more than 100 million albums and done more than $1B in box office returns. He said to me one day, “Ryan, it’s not enough that you read a lot. To do great things, you have to read to lead.”
What he meant was that in an age where almost nobody reads, you can be forgiven for thinking that the simple act of picking up a book is revolutionary. It may be, but it’s not enough. Reading to lead means pushing yourself–reading books “above your level.” In short, you know the books where the words blur together and you can’t understand what’s happening? Those are the books a leader needs to read. Reading to lead or learn requires that you treat your brain like the muscle that it is–lifting the subjects with the most tension and weight.
For me, that means pushing ahead into subjects you’re not familiar with and wresting with them until you can–shying away from the “easy read.” It means reading Feynman over Friedman, biographies over business books, and the classics over the contemporary. It worked wonders for me: at 19, I was a Hollywood executive, I was at 21 I was the director of marketing for a publicly traded company, and at 24 I’d worked on 5 bestselling books and sold my own to the biggest publisher in the world. I may have been a college drop out but I have had the best teachers in the world: tough books.
My apartment is filled with such books that on paper, I never should have been able to understand. It wasn’t easy to crack them, but with the secrets below I was able to. And the process starts before you even crack the spine of a new book.
Before the first page…
Break out of the School Mindset
The way you learn to read in the classroom is corrupted by the necessity of testing. Tests often have very little to do with proving that you know or care about the material but more about proving that you spent the time reading it. The easiest way to do this is picking obscure things from the text and quizzing you on them: “Name this passage” “What were the main characters in Chapter 4?” We carry these habits with us. Remember: now you’re reading for you.
Let’s say you’re reading the History of the Peloponnesian War
From Seneca
We haven’t time to spare to hear whether it was between Italy and Sicily that he ran into a storm or somewhere outside the world we know–when every day we’re running into our own storms, spiritual storms, and driven by vice into all the troubles that Ulysses ever knew.
Forget everything but that message and how to apply it to your life.
Ruin the Ending
When I start a book, I almost always go straight to Wikipedia (or Amazon or a friend) and ruin the ending. Who cares? Your aim as a reader is to understand WHY something happened, the what is secondary.
You ought to ruin the ending–or find out the basic assertions of the book–because it frees you up to focus on your two most important tasks: 1) What does it mean? 2) Do you agree with it? The first 50 pages of the book shouldn’t be a discovery process for you; you shouldn’t be wasting your time figuring out what the author is trying to say with the book. Instead, your energy needs to be spent on figuring out if he’s right and how you can benefit from it. Plus if you already know what happens, you can identify all the foreshadowing and the clues the first read through.
Read the Reviews
Find out from the people who have already read it, what they felt was important. From Amazon to the New York Times, read the reviews so you can deduce the cultural significance of the work–and from what it meant to others. Also by being warned of the major themes you can anticipate them coming and then actually appreciate them as they unfold. Tip: if you agree with their assessment of the work, go ahead and steal it once you’ve finished. You can’t copyright an opinion–this isn’t school, this is life.
The book itself…
Read the Intro/Prologe/Notes/Forward
I know, I know. It infuriates me too when what looks like a 200 page book turns out to have 80 pages of translator’s introduction, but that stuff is important. Every time I have skipped through it, I’ve had to go back and start over. Read the intro, read all the stuff that comes before the book–even read the editors notes at the bottom of the pages. This sets the stage and helps boost your knowledge going into the book. Remember: you need every advantage you can get to read a book above your level. Don’t skip stuff intended to add context and color.
Look It Up
If you’re reading to lead, you’re going to come across concepts or words you’re not familiar with. Don’t pretend like you understand, look it up. I like to use Definr or I use my phone to look stuff up on Wikipedia. With Military History, a sense of the battlefield is often necessary. Wikipedia is a great place to grab maps and to help understand the terrain. I was once trying to read some books on the Civil War and got stuck. 10 hours of Ken Burn’s documentaries later, the books were easy to breeze through (see, looking stuff up can be as easy as watching TV) That being said, don’t get bogged down with the names of the cities or the spelling of names, you’re looking to grasp the meta-lesson: the conclusions.
Mark Passages
I love Post-It Flags
After you finish…
Go Back Through
I have the same schedule with every book I read. After a mandatory 1-2 week waiting period after finishing, I go back through the book with a stack of 4×6 index cards. One these cards, I write out–by hand–all the passages I have noted as being important. It might seem strange but it’s an old tactic used by everyone from Tobias Wolff to Montaigne to Raymond Chandler. (Who once said: “When you have to use your energy to put those words down, you are more apt to make them count.” ) Each one of these cards is then assigned a theme and filed in my index card box. The result of 4-5 years of doing this? Thousands of cards in dozens of themes–from Love to Education to Jokes to Musings on Death. I return to these pieces of wisdom when I am writing, when I need help or when I am trying to solve a business problem. It has been an immense resource.
Read One Book from Every Bibliography
This is a little rule I try to stick with. In every book I read, I try to find my 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. Just keep a running list through Amazon’s Wish List service (here is mine). Last month I read a book on Evolutionary Psychology and discovered that I’d read almost 80% of its sources because I’d been pulled down the rabbit hole of a predecessor.
Apply and Use
You highlight the passages for a reason. Why type the quotes if you aren’t going to memorize and use them? Drop them in conversation. Allude to them in papers, in emails, in letters and in your daily life. How else do you expect to absorb them? The more fulfilling an outlet you find for the fruit of your database, the more motivated you will be to fill it. Try adding a line to a report you’re doing, find solace in them during difficult times or add them to Wikipedia pages. Do something.
I give you Seneca again:
My advice is really this: what we hear the philosophers saying and what we find in their writings should be applied in our pursuit of the happy life. 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.
Remember: we read to lead for moral and practical lessons. The point is to take what we’ve read and turn the words, as Seneca says, into works.
Conclusion: It’s on You
Of course, none of this is easy. People always ask me if the books I carry around are for school because they’re full of notes, flags and folded pages–why would anyone work so hard on something they were doing on their own? Because I enjoy it, because it’s the only thing that separates me from ignorance. These are the techniques have allowed me to leap years ahead of my peers. It’s how you strike out on your own and build strength instead of letting some personal trainer dictate what you can and can’t be lifting. It’s also expensive, I’ve purchased thousands of books and invested hours upon hours of time learning them. But how expensive is going back for an MBA? Or attending TED? I think there is more wisdom in the timeless books of the last 5,000 years than a conference or two–if you do it right and push yourself.
So try it: Do your research, read diligently without getting bogged down in details, and then work to connect, apply and use. It’s your job as a leader. And I think you’ll find that you’re able to read above your supposed “level” and that people will follow your example. If you put in the work, books, as the great writer and voracious reader Petrarch once said, will pay you back:
“Books give delight to the very marrow of one’s bones. They speak to us, consult with us and join with us in a living and intense intimacy.”
Enjoy the journey.
Note: This is just my system and its by no means all inclusive. However, since posting a version of it on my blog in 2007 it has been seen hundreds of thousands of times and discussed everywhere from Lifehacker to college classrooms. 
