Read to Lead: How to Digest Books Above Your “Level”


I shouldn’t be able to read most of the books on my shelf. I never took a single classical history class and I cheated through most of Economics 001. Still, the loci of my library are Greek History and Applied Economics. And though they often are beyond me educationally, I’m able to comprehend them because of some equalizing tricks. 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.”

This is how I break down a new book:

Before the First Page
Break out of the School Mindset

Almost everything you learn in the classroom is tainted by the fact that ultimately teachers have to test you on it. 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?” So forget that–you’re reading for you. Even when you’re in school, you should be reading for yourself and not for the teacher. The worst thing that can happen is they knock you down a little bit on a grade that means very little.

When you read History of the Peloponnesian War, the countries involved in the conflict between Corinth and Corcyra is not really worth remembering. (Proof: I had to go look up the names on Wikipedia, all I remember was that they both started with a C. )What you should latch onto is that as the two fought for allied support from Athens, one took the haughty “you owe us a favor” route and the other alluded to all the benefits that would come from aiding them. Guess who got the support?

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.”

He rightly points out that Homer was wise before he recited or sat down to write his own works–so what do you really gain by analyzing the minutia of it? The work is an expression of the message, not the message itself. So forget everything but that message and how to apply it to your life. Dates, names, pronunciations–they only matter in how they provide context for the lesson at hand. They carry little value otherwise.

Ruin the Ending

I almost always go straight to Wikipedia and ruin the ending. Who cares? Your aim as a reader is to understand WHY something happened, the what is secondary. In the case of HOTPW, without reading the entry you might have passed over the glorious anecdote that Thucydides missed a large part of the war because he caught the Plague and that he was largely delegated to writing about the battles because his military incompetence led to an early defeat.

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. 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 (Amazon)

Find out from the people who have already read it what they felt was important. From the reviews you can deduce the culture significance of the work–and from what it meant to others, at least grasp a bearing of what it could mean to you. Also by being warned of the major themes you can anticipate them coming and then actually appreciate them as they unfold. Which again frees you up much in the same way that ruining the ending does. And frankly, if you agree with their assessment of the work, go ahead and steal it once you’ve finished. They didn’t copyright it–this isn’t school, this is life.

The Book Itself
Read the Intro

I know, I know. It infuriates me too that a 200 page book has a 80 page translator’s introduction, but they are helpful. Every time I have skipped through it, I’ve had to go back and start over. Read the intro. It often has a ton of interesting stuff about who the work ended up influencing, and other tidbits that often stick with you longer than the work itself.

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 Blackberry to look stuff up on Wikipedia. If you’re away from a computer and need the definition of a word, type “Define: ______” and text it to 46645 (Googl) and you’ll get one back from Google. 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. 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 conclusion.

Post It Highlighters

These will change how you read. On the right side of the page, I tag the pages I have highlighted important passages on. On the top of the page, I mark if there is a concept I need to research or if there is a book the author suggests I read as a supplement. Don’t be afraid to tear the book up with tags–tape is cheap but the time it will take you to otherwise flip back through the book to track something down is not.

Flip Through It Again

Before you close the book, go back through and reread all the passages you’ve marked. This puts them back into your memory and let’s you walk away knowing the crucial hits of the author’s message. With these flagpoles you will be able to go back through and remember the details if necessary, like knowing the chord structure of a song and working through the rest as it comes.

After You Finish
Type Out the Important Quotes and Passages

In Old School, Tobias Wolff talks about how he used to retype the works of classic authors when he felt uninspired just to feel what it was like to have that profoundness flow out of his finger tips. That is why I have the Book Quotes and Passages section. I’ve been compiling for almost 4 years now and have nearly 15,000 words typed. And I still have boxes left to go through. Not only will it inspire you, but it will help you remember them.

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.

Connect, Apply, Use

When you make connections–that the cultural reactions after WWI (largely extroverted and flamboyant) and WWII (introverted, uptight and overly moral) appear to be opposite takes on the same disillusionment–you can see things for what they are. And then better understand the cyclical nature of history and human nature. Make the connection–that every major military pretext for war was claimed by (some) historians to be governmentally orchestrated (sinking of the Maine, Pearl Harbor, the Gulf of Tonkin incident, 9/11)–and appreciate how our responses to events rarely ever contain perspective or a sense of rational continuity. Ex: Is Cicero’s advice on speaking similar to the mechanics of good writing?

Begin to apply the mindset of the author to your daily life–even if you don’t agree with it. How would an evolutionary psychologist consider this situation? If people are economically self-interested, how can I explain this action? If Von Clausewitz said that we love Greek history because it’s the easiest to manipulate, should I trust this anecdote? Ex: I know Cicero wanted to make you a better speaker, but if he wanted you to write better, what would he say?

Use. You highlight the passages for a reason. Why type the quotes if you aren’t going to memorize 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? Don’t be a douche and drop them where they aren’t relevant, but use the wisdom to make yourself a better person.Ex: Write, even if it’s just for yourself, even if you’re thinking aloud, what Cicero can teach you about writing.

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.”


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.

So try it: Do your research, read diligently without getting bogged down in details, and then work to connect, apply and use. And I think you’ll find that you’re able to read above your supposed “level” even outside the classroom setting.

You can check out my Reading List for a place to start.

**Note: My list isn’t conclusive, it’s just my system. If there are any steps I am missing, feel free to post what you use.

Written by Ryan Holiday
Ryan Holiday is the bestselling author of Trust Me, I’m Lying, The Obstacle Is The Way, Ego Is The Enemy, and other books about marketing, culture, and the human condition. His work has been translated into thirty languages and has appeared everywhere from the Columbia Journalism Review to Fast Company. His company, Brass Check, has advised companies such as Google, TASER, and Complex, as well as Grammy Award winning musicians and some of the biggest authors in the world. He lives in Austin, Texas.