13 Strategies That Will Make You A Better Reader (And Person)

Reading is a good thing. A good thing too many people don’t do enough of (or any of it all…) So obviously doing lots of it is good, right? This is why people try to figure out how to speed read (a scam, I say!). This is why they show off their huge libraries (guilty!). This is why they listen to audiobooks at 2x or 3x speed. 

“Less is more? Quality over quantity? Not with books!” 

But not all reading is created equal. As Epictetus said, “I cannot call somebody ‘hard-working’ knowing only that they read.” He said he needed to know what and how they read. Sure, reading is better than a lot of other activities, but you can still do it poorly or for poor reasons. “Far too many good brains,” Seneca said, “have been afflicted by the pointless enthusiasm for useless knowledge.”

To be a great reader, it is not enough that you read, it’s how you read. These 13 strategies by no means make a complete list, but if you implement even a couple of them, I’m comfortable guaranteeing you’ll not only be a better reader for it, but a better person too.

Stop Reading Books You Aren’t Enjoying 

If you find yourself wanting to speed up the reading process on a particular book, you may want to ask yourself, “Is this book any good?”

You turn off a TV show if it’s boring. You stop eating food that doesn’t taste good. You unfollow people when you realize their content is useless.

Life is too short to read books you don’t enjoy reading. My rule 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 to endure crappy books less and less.

Read Like A Spy

One of the most surprising parts of Seneca’s writing is how that avowed Stoic quotes Epicurus, the founder of Epicureanism. Even Seneca knew this was strange as each time he did so in his famous Letters, he felt obliged to preface or explain why he was so familiar with the teachings of a rival school.

His best answer appears in Letter II, On Discursiveness in Reading, and it works as a prompt for all of us in our own reading habits. The reason he was so familiar with Epicurus, Seneca wrote, was not because he was deserting the writings of the Stoics, but because he was reading like a spy in the enemy’s camp. That is, he was deliberately reading and immersing himself into the thinking and the strategies of those he disagreed with. To see if there was anything he could learn and, of course, to bolster his own defenses.

Keep A Commonplace Book

In his book, Old School, Tobias Wolf’s semi-autobiographical character takes the time to type out quotes and passages from great books to feel great writing come through him. I do this almost every weekend in what I call a “commonplace book”— a collection of quotes, ideas, stories and facts that I want to keep for later. It’s made me a much better writer and a wiser person. I am not alone. In 2010, when the Reagan Presidential Library was undergoing renovation, a box labeled “RR’s desk” was discovered. Inside the box were the personal belongings Ronald Reagan kept in his office desk, including a number of black boxes containing 4×6 note cards filled with handwritten quotes, thoughts, stories, political aphorisms, and one-liners. They were separated by themes like “On the Nation,” “On Liberty.” “On War,” “On the People,” “The World,” “Humor,” and “On Character”. This was Ronald Reagan’s version of a commonplace book. Lewis Carroll, Walt Whitman, Thomas Jefferson all kept their own version of a commonplace book. 

As Seneca advised, “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.”

Re-Read The Masters

You were in high school when you read The Great Gatsby for the first time. You were just a kid when you read The Count of Monte Cristo or had someone tell you the story of Odysseus. 

The point is: You got it right? You read them. You’re done, right? Nope.

We cannot be content to simply pick up a book once and judge it by that experience. It’s why we have to read and re-read. As Seneca put it, “You must linger among a limited number of master-thinkers, and digest their works, if you would derive ideas which shall win firm hold in your mind.” Because the world is constantly changing, we are changing, and therefore what we get out of those books can change. It’s not enough to read the classics once, you have to read them at every age, every era of your life. We never step in the same river twice, Marcus Aurelius said, and that’s why we must return again and again to the great works of history.

Read Fiction

There’s an interesting thread running through in the writings and teachings of Marcus Aurelius, Seneca, and Epictetus that can zip right past you if you aren’t reading closely. What is it? What did all these great men share? They heavily relied on plays, tragedies, satires, mythologies, and other works of fiction to clarify their thinking and their own writing.

Epictetus draws on characters like Achilles and Agamemnon from the Iliad, Admetus from Euripides’ Alcestis, and a long list of others from Greek mythology. Marcus Aurelius quotes from the comedies of Aristophanes, the tragedies and plays of Euripides and Sophocles, and says we should read fiction “to remind us of what can happen, and that it happens inevitably—and if something gives you pleasure on that stage, it shouldn’t cause you anger on this one.” Seneca liked to quote the works of the great Roman poets Virgil and Lucius Accius, the legendary Homer, the playwright Plautus, and he wrote many brilliant plays himself. 

Yet, many people—even those with a voracious reading habit—make the same mistake: They hardly, if ever, read fiction. They even brag about it! They’re too busy. They don’t have time for “art.” There’s plenty of “real” stuff—the characters in fiction that bear little resemblance to the world we know? I don’t have time for it. But fiction, like all wonderful art, is filled with beautiful bits of insight about the human condition. It can change your life and teach you just as much as any non-fiction book. Actually, no, it can teach you more! It can shine a light on universal truths that non-fiction, bounded by the facts and figures of its specific world, often cannot (to say nothing of the research that connects literature with improved empathy, reduced stress, and hone social skills).

Read Before Bed

Speaking of reading fiction, the great William Osler (founder of John Hopkins University and a fan of the Stoics) told his medical students it was important that they turn to literature as a way to nourish and relax their minds. “When chemistry distresses your soul,” he said, “seek peace in the great pacifier, Shakespeare, ten minutes with Montaigne will lighten the burden.” He told his students to read to relax and to be at leisure. To keep their minds strong and clear.

Instead of turning to the TV or to Twitter, let us follow Osler’s advice:

“Start at once a bedside library and spend the last half-hour of the day in communion with the saints of humanity. There are great lessons to be learned from Job and from David, from Isaiah and St. Paul. Taught by Shakespeare you may take your intellectual and moral measure with singular precision. Learn to love Epictetus and Marcus Aurelius. Should you be so fortunate as to be born a Platonist, Jowett will introduce you to the great master through whom alone we can think in certain levels, and whose perpetual modernness startles and delights. Montaigne will teach you moderation in all things, and to be ‘sealed of his tribe’ is a special privilege.”

Ask People You Admire For Book Recommendations

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 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.)

If a book changed someone’s life — whatever the topic or style — it’s probably worth the investment. If it changed them, it will likely at least help you.

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.

You have to read and approach reading accordingly. Montaigne once teased the writer Erasmus, who was known for his dedication to reading scholarly works, by asking with heavy sarcasm, “Do you think he is searching in his books for a way to become better, happier, or wiser?” In Montaigne’s mind, if he wasn’t, it was all a waste.

Don’t Just Learn From Experience

“If you haven’t read hundreds of books,” the soldier-philosopher General James Mattis says, “you’re functionally illiterate.” Human beings have been fighting and dying and struggling and doing the same things for eons. To not avail yourself of that knowledge is profoundly arrogant and stupid. To paraphrase Mattis, it is unconscionable to fill up body bags while you get your education only by experience. It’s worse than arrogant. It’s unethical, even murderous. 

Well, the same is true for much less lethal professions. How dare you waste your investor’s money by not reading and learning from the mistakes of other entrepreneurs? How dare you so take your marriage or your children for granted that you think you can afford to figure this out by doing the wrong things first?

Too much depends on you for you to learn solely by experience—you have to also learn by the experiences of others. Drink deeply from history, from philosophy, from the books of journalists and the memoirs of geniuses. Study the cautionary tales and the screw ups, read about failures and successes. Read constantly—read as a practice.

Because if you don’t, it’s a dereliction of duty.

Study The Past To Understand The Present

“I don’t have time to read books,” says the person who reads dozens of breaking news articles each week. “I don’t have time to read,” they say as they refresh their Twitter feed for the latest inane update. “I don’t have time to read fiction—that’s entertainment,” they say as they watch another panel of arguing talking heads on CNN, as if that’s actually giving them real information they will use. 

Being informed is important. It is the duty of every citizen. But we go about it the wrong way. We are distracted by breaking news when really we should be drinking deeply from the great texts of history. Because the truth is that most truths are very old. In fact, it’s these timeless truths that teach us more about the future and about our current times than most of our contemporary thinking. 

The actor Hugh Jackman said in an interview that he gets his news by keeping his eye on the big picture—going through the Ken Burns catalog and reading books like Meditations. “That’s the way you should understand events and humanity,” he said, “with that sort of 30,000-foot view.” If you want to be informed, study the past.

Aim For Quality, Not Quantity

The philosopher Mortimer Adler talked about how the phrase “well-read” has lost its original meaning. We hear someone referred to as “well-read” today and we think someone who has read lots of books. But the ancients would have thought someone who really knows their stuff, who has dived deep in a few classic texts to the point that they truly understand them. “A person who has read widely,” Mortimer says of the modern reader, “but not well deserves to be pitied rather than praised.” The early 17th century philosopher Thomas Hobbes joked similarly, “If I read as many books as most men do, I would be as dull-witted as they are.”

You don’t have to read hundreds and hundreds of books. In fact, most people who make it their goal to read a certain amount of books each year inevitably fall off pace, get discouraged, and stop reading altogether. You’ll both read more and get a better return on your investment if you do what the Stoics advised. As Marcus Aurelius would say, don’t be satisfied with just “getting the gist” of things you read. “Read attentively,” he said. Read deeply. Read repeatedly. Aim for quality, not quantity. 

Get Out Of A Dry Spell

The path to wisdom is not a straight one. The journey is long and circuitous. It’s a windy road with twists and turns, ups and downs, highs and lows. Maybe you’re in the middle of one of those lows yourself right now, at the bottom of the valley. This can be a scary place to be, because without the proper perspective it can feel like you’re going to be stuck there forever. You take a few steps in one direction, and it feels like you haven’t gotten anywhere. The top of the mountain is just as far away, if not more distant. 

There is a term for this phenomenon: being stuck in a slump. A reading slump always pops up for me, for instance, during a book launch when it’s nearly impossible to concentrate enough to read. I’m busy. I’m fried. For a variety of reasons, the result is always a reading dry spell. But I’ve found I’m able to get back into it by rereading something that has really spoken to me in the past. Instead of expecting a random book I pick up to really speak to me, I go back to something that has already spoken volumes…and find out how much more it has to say. I’ll grab a new translation of Marcus Aurelius and see him from a different view. I’ll go reread a favorite novel, such as A Man in Full or The Moviegoer or Memoirs of Hadrian

Join A Program

In 2018, we did our first Daily Stoic Challenge, full of different challenges and activities based on Stoic philosophy. It was an awesome experience. Even I, the person who created the challenge, got a lot out of it. Why? I think it was the process of joining a program. It’s the reason personal trainers are so effective. You just show up at the gym and they tell you what to do, and it’s never the same thing as the last time.  Deciding what we want to do, determining our own habits, and making the right choices is exhausting. Handing the wheel over to someone else is a way to narrow our focus and put everything into the commitment.

And if you are serious about becoming a great reader, the Stoics can help. We built out their best insights into our Read to Lead: A Daily Stoic Reading Challenge. Since it first launched in 2019, Read to Lead has been our most popular challenge, taken on by almost ten thousand participants. We recently announced that, for the first time ever, registration to join the 2022 live cohort is officially open.

The 2022 live course will take place across 5 weeks at a pace of 2 emails a week (~30,000 words of exclusive content). Additionally, there will be weekly live video sessions with me! It’s one of my favorite things to get the chance to interact with everyone in the course—I would love to have you join us. You can learn more here! But it closes May 16 at Midnight so don’t wait.

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