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RyanHoliday.net - Meditations on strategy and life
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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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May 11, 2022by Ryan Holiday
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18 Little Stories That Will Have Massive Impact On Your Life

When I was 18 years old, I was a research assistant to Robert Greene. My job was to find stories he could use in his writing. Nearly seventeen years later, I still use so much of what Robert taught me about finding great stories in researching for my own writing. But the gift has been less in how it has helped me professionally, and more in how it has helped me personally. 

As I would learn much later, Robert was teaching me how to find what the ancient Greeks called a chreia: “an exemplary story about a famous person, often culminating in a memorable utterance,” as Gregory Hays has defined it. “Learning by precepts is the long way around,” Seneca wrote. “The quick and effective way is to learn by example.” In this article, I thought I would share a handful of my favorite stories I have found over the years—ones that have stuck with me and that I think will have a lasting impact on your life.

Enough.

The writers Kurt Vonnegut (Slaughterhouse Five) and Joseph Heller (Catch-22) were at a glamorous party outside New York City. Standing in the palatial second home of the billionaire host, Vonnegut began to needle his friend. “Joe,” he said, “how does it feel that our host only yesterday may have made more money than your novel has earned in its entire history?”

“I’ve got something he can never have,” Heller replied.

“The knowledge that I’ve got enough.”

How you do anything is how you do everything.

On the campaign trail, a heckler once tried to embarrass President Andrew Johnson by shouting about his working-class credentials. Johnson replied without breaking stride: “That does not disconcert me in the least; for when I used to be a tailor I had the reputation of being a good one, and making close fits, always punctual with my customers, and always did good work.”

Anything you do well is noble, no matter how humble.

Just work.

The dancer Martha Graham tells a story about her vaudeville days, when she was followed by a bird act. When the music went on the white cockatoos, trained by years of reinforcement and ritual, would become almost hysterical with excitement, clawing and beating at the cage until they go on stage and perform. “Birds, damnit, birds!,” she would yell at students who didn’t give their full commitment. The birds can’t want it more than you can. 

As they say in the Army, “You don’t have to like it. You just have to do it.” 

Always stay a student.

Late in his reign, a friend stopped Marcus Aurelius as he was leaving the palace, carrying a stack of books. Finding this to be a surprising sight, the man asked where Marcus was going. He was off to attend a lecture on Stoicism, he said, for “learning is a good thing, even for one who is growing old. From Sextus the philosopher I shall learn what I do not yet know.”

That’s right, even as the most powerful man in the world, Marcus was still taking up his books and heading to class.

It’s harder to be kind than clever. 

When he was a young boy, Jeff Bezos was with his grandparents, both of whom were smokers. Bezos had recently heard an anti-smoking PSA on the radio that explained how many minutes each cigarette takes off a person’s lifespan. And so, sitting there in the backseat, like a typical precocious kid, he put his math skills and this new knowledge to work and proudly explained to his grandmother, as she puffed away, “You’ve lost nine years of your life, Grandma!”

The typical response to this kind of innocent cheekiness is to pat the child on the head and tell them how smart they are. Bezos’ grandmother didn’t do that. Instead, she quite understandably burst into tears. It was after this exchange that Bezos’ grandfather took his grandson aside and taught him a lesson that he says has stuck with him for the rest of his life. “Jeff,” his grandfather said, “one day you’ll understand that it’s harder to be kind than clever.”

Your work is the only thing that matters.

A young comedian approached Jerry Seinfeld in a club one night and asked him for advice about marketing and getting exposure.

Exposure? Marketing? Seinfeld asks. Seinfeld, a pure stand-up, a comedian’s comedian, is appalled by the question. It’s offensive to his legendary heads-down work ethic. But to the kid, this was a surprise. Isn’t that the kind of question you’re supposed to ask? Isn’t that how you get ahead?

Just work on your act, Seinfeld said.

Get moving.

As a young woman, Amelia Earhart aspired to be a great aviator. But it was the 1920s, and people still thought women were frail and weak and didn’t have the stuff. Woman suffrage wasn’t even a decade old. She couldn’t make her living as a pilot, so she was working as a social worker. 

Then one day the phone rang. A donor had been willing to fund the first female transatlantic flight. But there was a catch: Amelia wouldn’t get to actually fly the plane. She’d have to sit in the back like “a sack of potatoes,” as she put it. And not only that—the two male pilots were going to get paid, but she wouldn’t get paid anything.

Guess what she said to the offer? She said yes. Because that’s what people who defy the odds do. That’s how people who become great at things—whether it’s flying or blowing through gender stereotypes—do. They start. Anywhere. Anyhow. They don’t care if the conditions are perfect or if they’re being slighted. They swallow their pride. They do whatever it takes. Because they know that once they get started, if they can just get some momentum, they can make it work. And they can prove the people who doubted them wrong, as Earhart certainly did.

They still hide money in books.

As a young boy, the famed basketball coach George Raveling learned an invaluable lesson from his grandmother, who raised him. As they were preparing dinner in the kitchen one evening she began to tell him about how in the days of slavery, the plantation owners would hide their money in books on the shelves of their libraries. “Why did the slave masters hide their money in books, George?” she asked him.

“I don’t know Grandma,” George replied, “why did they do that?”

“Because they knew the slaves couldn’t read,” she said, “so they would never take the books down.”

There’s a reason it was illegal to teach slaves to read. There is a reason that every totalitarian regime has burned and banned books. Knowledge is power. It sounds like a cliche, but cliches only sound that way because of the generally accepted truth at their core. 

How to create anything of consequence.

Plutarch tells the story of a rich Delian ship owner who was asked how he built his fortune. “The greater part came quite easily,” he said, “but the first, smaller part took time and effort.”

Creating anything of consequence or magnitude requires deliberate, incremental, and consistent work. “Well-being is realized by small steps,” Zeno would say, looking back on his life, “but is truly no small thing.”

Be the red.

In a famous exchange, the Stoic philosopher Agrippinus explained why he was spurning an invitation to attend some banquet being put on by Nero. Not only was he spurning it, he said, but he had not even considered associating with such a madman. 

A fellow philosopher, the one who had felt inclined to attend, asked for an explanation. Agrippinus responded with an interesting analogy. He said that most people see themselves like threads in a garment—they see it as their job to match the other threads in color and style. They want to blend in, so the fabric will match. But Agrippinus did not want to blend in. “I want to be the red,” he said, “that small and brilliant portion which causes the rest to appear comely and beautiful…’Be like the majority of people?’ And if I do that, how shall I any longer be the red?”

Use it all as fuel.

At age sixty-seven, Thomas Edison was eating dinner with his family when a man came rushing into his house with urgent news: A fire had broken out at Edison’s research and production campus a few miles away. Fire engines from eight nearby towns rushed to the scene, but they could not contain the blaze. Fueled by the strange chemicals in the various buildings, green and yellow flames shot up six and seven stories, threatening to destroy the empire Edison had spent his life building.

Edison calmly but quickly made his way to the fire, through the now hundreds of onlookers and devastated employees. Finding his son standing shellshocked at the scene, Edison would utter these famous words: “Go get your mother and all her friends. They’ll never see a fire like this again.”

The Stoics loved the metaphor of fire. Marcus Aurelius would write that “a blazing fire makes flame and brightness out of everything that is thrown into it.” That’s what Edison did. He did not despair. He did not weep. He did not rage. Instead, he got to work. He told a reporter the next day that he wasn’t too old to make a fresh start, “I’ve been through a lot of things like this. It prevents a man from being afflicted with ennui.” 

Do what you have to do. 

Before the Civil War, Ulysses S. Grant experienced a long chain of setbacks and financial difficulties. He washed up in St. Louis, selling firewood for a living—a hard fall for a graduate of West Point. An army buddy found him and was aghast. “Great God, Grant, what are you doing?” he asked. Grant’s answer was simple: “I am solving the problem of poverty.”

Never question another man’s courage.

After he became premier of the Soviet Union, Nikita Khrushchev was onstage, speaking to the Politburo, denouncing the crimes of Stalin’s regime. Anonymously, some unnamed member passed a note to the front of the room. “Yes,” it said, “but where were you at the time?”

Without a beat, Khrushchev, with an intimidating tone, shouted and asked who wrote the note. Silence. “I was where you are now,” Khrushchev. Meaning, in the audience. Anonymous. Intimidated. Doing nothing. Just like everyone else. 

Alter your approach.

As a young working actor, George Clooney struggled with how to tackle his audition process. Clooney was always concerned about the problem that he faced: how to book an acting job and earn some much-needed income. How did he deal with this? 

Clooney turned the situation around and had a realization: the audition was also an obstacle for the producers, who needed to find someone to fill the role and do an amazing job. Clooney began to approach his auditions from a different angle. Instead of going into his auditions as someone trying to get a job, he approached them as someone who could help the producers do theirs better. As a result, he began landing roles and would eventually become one of Hollywood’s most celebrated leading men.

You only control the effort, not the results.

John Kennedy Toole’s great book A Confederacy of Dunces was universally turned down by publishers, news that so broke his heart that he later committed suicide in his car on an empty road in Biloxi, Mississippi. 

After his death, his mother discovered the book, advocated on its behalf until it was published, and it eventually won the Pulitzer Prize.

What changed between those submissions? Nothing. The book was the same. It was equally great when Toole had it in manuscript form and had fought with editors about it as it was when the book was published, sold copies, and won awards. If only he could have realized this, it would have saved him so much heartbreak. He couldn’t, but from his painful story we can at least see how arbitrary many of the breaks in life are.

Good things happen in bookstores.

On a merchant voyage in Athens in the 4th Century BC, a man named Zeno was shipwrecked. He lost everything. He washed up in Athens where he walked into a bookstore and listened to the bookseller reading dialogues from Socrates. After the reading, Zeno asked the question that would change his life: “Where can I find a man like that?” and in so doing, he began a philosophical journey that led to the founding of Stoicism and then, to the brilliant works of Seneca, Epictetus, and Marcus Aurelius — which, not lost to history, are beginning to find a new life on bookshelves today. From those heirs to Zeno’s bookshop conversion, there is a straight line to many of the world’s greatest thinkers, and even to the Founding Fathers of America.

All from a chance encounter in a bookshop. According to the ancient biographer Diogenes Laertius, Zeno joked, “Now that I’ve suffered shipwreck, I’m on a good journey,” or according to another account, “You’ve done well, Fortune, driving me thus to philosophy,” he reportedly said. 

On the window of our shop, The Painted Porch—named after the Stoa Poikile (“Painted Porch”) where Zeno taught his classes—we have written in large letters: “Good things happen in bookstores.”

Big ones, small ones, corporate or independent ones. Where books are browsed, new ideas are introduced to older readers, while old ideas are introduced to newer readers. And perspectives shift just the same. Couples connect. Experiences are shared. Worlds are built—in the pages of the books being browsed, and in the lives of those doing the browsing.

Follow the process.

There’s a story of the great 19th-century pioneer of meteorology, James Pollard Espy, and a chance encounter as a young man. Unable to read and write until he was 18, Espy attended a rousing speech by the famous orator Henry Clay. After the talk, a spellbound Espy tried to make his way toward Clay, but he couldn’t form the words to speak to his idol. One of his friends shouted out for him: “He wants to be like you, even though he can’t read.”

Clay grabbed one of his posters, which had the word CLAY written in big letters. He looked at Espy and said, “You see that, boy?” pointing to a letter. “That’s an A. Now, you’ve only got 25 more letters to go.”

As Heraclitus observed, “under the comb, the tangle and the straight path are the same.” There is no task, however seemingly mammoth, that is not just a series of component parts.

Remember that you will die.

In late 1569, a French nobleman named Michel de Montaigne was given up as dead after being flung from a galloping horse. As his friends carried his limp and bloodied body home, Montaigne watched his own life slip away, like some dancing spirit on the “tip of his lips,” only to have it return at the last possible second. This sublime and unusual experience marked the moment Montaigne changed his life. Within a few years, he would be one of the most famous writers in Europe. After his accident, Montaigne went on to write volumes of popular essays, serve two terms as mayor, travel internationally as a dignitary, and serve as a confidante of the king.

It’s a story as old as time. Person nearly dies, takes stock, and emerges from the experience a completely different, and better, person. And this is the old philosophical idea of memento mori—”remember that you will die.” In his Meditations, Marcus Aurelius wrote, “you could leave life right now. Let that determine what you do and say and think.” Never assume that you have a firm grasp on life because it could slip from your fingers at any moment.

***

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May 4, 2022by Ryan Holiday
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Here’s Your Secret To Success: Go The F*ck To Sleep

Some people take pride in how little they sleep. It’s proof of their hard work, their dedication, their determination.

Me?

I’m prouder of the exact opposite.

Despite producing over a dozen books, writing my daily emails for Daily Stoic and Daily Dad, reading books to recommend to my Reading List Email each month, opening and operating The Painted Porch Book Shop, and spending lots of time with my wife and kids—I’ve never pulled an all-nighter. My writing pace is not fueled by stimulants. My productivity is not dependent on adrenaline. My work doesn’t interfere with my sleep. The only thing that has ever kept me up and busy in the middle of the night have been my young children.

In the military they speak of sleep discipline–meaning it’s something you have to be good at, you have to be conscious of, something you can’t let slip. We only have so much energy for our work, for our relationships, for ourselves. A smart person knows this and guards it carefully. A smart person knows that getting their 7-8 hours of sleep every night does not negatively affect their output, it contributes crucially to their best work.

So in this article, I am going to give you the 13 strategies that have been the secret to my success. Some of them you may have come by before. Others you probably haven’t. But all of them work.

Beware Burnout

Arianna Huffington quietly grew The Huffington Post into a behemoth with some 200 million unique visitors a month and 17 international editions. Her stake in Huffington Post was worth an estimated $21 million. But for a time, Arianna’s wealth and power came at the expense of living a good life. After years of working upwards of 18-hour days seven days a week, the sleep tax collectors showed up. Arianna was in her home office when she collapsed, hit her head on her desk, broke a cheekbone, and woke up in a pool of her own blood. At the hospital, doctors ran several tests. Brain MRI. CAT scans. Heart sonograms. Her diagnosis? Burnout.

But unlike so many overworked people, however, Arianna was able to look in the mirror after this harrowing incident and do what too many are unable to do: she changed. She realized that life was about more than just doing, that there was no glamor in working oneself to the bone, trading sleep for an extra conference call or a few minutes on television or a meeting with an important person. So, despite being at her peak financially and professionally, she left The Huffington Post, went looking for what she would call the “third metric” of success, and launched Thrive Global, where she’s brought the resources of both science and philosophical wisdom to combat the rising epidemic of stress and burnout.

Near the end of his life, Marcus Aurelius sat down and wrote about what he learned from the mentor who most shaped his life: his adopted step-father Antoninus. Antoninus worked hard, Marcus wrote, but he also made sure “to take adequate care of himself…With the result that he hardly ever needed medical attention, or drugs or any sort of salve or ointment.” Marcus said that life is short and if we practice bad habits, if we don’t take care of ourselves, if we aren’t willing to change, we will surely shorten that time.

You Are Not An Exception

People say, I do perfectly fine on four or five hours of sleep. No, you don’t. I’m an exception. No, you’re not. 

In a study by a team of scientists at the Division of Sleep and Chronobiology in the Department of Psychiatry at the University of Pennsylvania, participants were divided into four groups: one was sleep deprived for up to 88 hours, one group slept for four hours a night, one group slept for six hours a night, and one group slept for eight hours a night. There were two important findings. First, the performance of the groups who slept four and six hours was as impaired as the sleep deprived group. Second, when asked, all participants grossly miscalculated how impaired they were.

As Dr. Thomas Roth, the Director of the Sleep Disorders and Research Center at Henry Ford Hospital in Detroit, put it, “The number of people who can survive on five hours of sleep or less without any impairment, expressed as a percent of the population, and rounded to a whole number, is zero.” Or if not zero, close enough to zero that we can assume it doesn’t include you. 

Sleep With Your Phone in the Other Room

Sen. Ben Sasse of Nebraska is known for giving his young staffers old-school alarm clocks — not because he wants to make sure they’re on time for work, but so they don’t have an excuse to sleep with their phone on the nightstand. If you have an alarm that’s not your clock app, your phone can go in the other room, and if your phone is in the other room, you can’t check it at night.

This means you won’t know if you get a text message or an email. It means you won’t be tempted to scroll through social media. It means you won’t be staring at a screen that are, as Matthew Walker writes in Why We Sleep, “artificially forcing us awake, thereby masking our  natural tiredness at night, [which] keeps people awake for longer, and makes falling asleep more difficult.”

Wake Up Early

I have written many times about the power of waking up early. The mornings are the most productive hours of the day—before the interruptions, before the distractions, before the rest of the world gets up and going too. Early, we are free. Hemingway would talk about how he’d get up early because early, there was “no one to disturb you and it is cool or cold and you come to your work and warm as you write.” Toni Morrison found she was just more confident in the early morning, before the day had exacted its toll and while the mind was fresh. Like most of us, she realized she was just “not very bright or very witty or very inventive after the sun goes down.” Who can be? After a day of banal conversations, frustrations, mistakes and exhaustion. 

And of course, when you get up with the sun, you are more likely to wind down with the sun. It was one of Seneca’s observations: we were made to follow the rhythm of the sun. “We are more industrious, and we are better men if we anticipate the day and welcome the dawn,” he wrote, “but we are base churls if we lie dozing when the sun is high in the heavens, or if we wake up only when noon arrives.” If you want the secret to success, if you want to start executing at a higher level, then you have to get in the habit of waking up early. You have to come to the realization that you are at your best when you are in rhythm with the sun.

Strenuous Exercise Every Day

I take a walk and go for a run just about every day. It’s not about burning calories or getting the heart rate up or training for a marathon. “It is indeed foolish,” Seneca wrote, “to work hard over developing the muscles and broadening the shoulders and strengthening the lungs.” Rather, he said, the goal of exercise is simply to “tire the body” so we can later enjoy a heavy sleep. 

The ancients didn’t need the research, but it is nice knowing what we now know. Matthew Walker writes of the “clear bidirectional relationship” between exercise and sleep. Physical activity leads to better sleep which boosts physical activity which leads to better sleep which, so on and so on. “It is clear,” Walker writes in Why We Sleep, “that a sedentary life is one that does not help with sound sleep, and all of us should try to engage in some degree of regular exercise to help maintain not only the fitness of our bodies but also the quantity and quality of our sleep.” Make it a rule, as I have: strenuous exercise every single day.

Go The F*ck To Sleep

You think you’re not an early morning person…but that’s mostly because you’re not going to bed early enough. You’re staying up to what? Scrolling through TikTok or tweets at 11pm? You should be asleep!

When you’re burned out, when you’re exhausted, when you’ve had that long day where all you want to do is veg out on the couch? That’s precisely when you need the extra discipline to get up and go to bed. Follow the advice of a book I love to read to my kids: Go the F*ck to Sleep! 

Morning routines are great but a bedtime routine is important too. Being disciplined about wrapping up and winding down is essential. 

Read Before Bed

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.”

Journal Before Bed

“Is there anything finer than this practice of examining one’s entire day?” Seneca asked. “Think of the sleep that follows this self-inspection,” he said, “how peaceful, deep, and free, when the mind has been either praised or admonished, when the sentinel and secret censor of the self has conducted its inquiry into one’s character.”

That’s what a great night’s sleep requires. A mental state free of clutter and chaos. It is a state that is never not hard to achieve, because each day presents plenty of opportunities to clutter or minds—responsibilities, the dysfunctional job that stresses you out, a contentious relationship, reality not agreeing with your expectations. But journaling is a tool uniquely suited to help us declutter our minds. A couple thousand years after Seneca intuited it, the Journal of Experimental Psychology proved that journaling before bed decreases cognitive stimulus, rumination, and worry, allowing you to fall asleep faster. So tonight, try Epictetus’s nightly ritual and see what it can do for you:

“Allow not sleep to close your wearied eyes, Until you have reckoned up each daytime deed: ‘Where did I go wrong? What did I do? And what duty’s left undone?’ From first to last review your acts and then Reprove yourself for wretched [or cowardly] acts, but rejoice in those done well.”

Treat The Weekends The Same

It almost doesn’t matter what the problem is, the solution is often a consistent routine. Tell a sleep expert you’re not sleeping well, that’s what they’ll suggest. Tell a psychiatrist you’ve been feeling anxious, that’s what their first question will be. Tell a productivity guru your work output isn’t where you want it, that’s where they’ll start. Tell a dog trainer your dog is acting up, that’s where they’ll start. Tell a strength trainer you want to get stronger, tell an author you want to get better at writing, tell the Stoics you want to round out the day in a calmer, more tranquil state—a consistent routine will be the answer.

Regardless of the practices you implement from above, the best thing you can do for your sleep is be consistent, seven days a week. “There is much we can do to secure a far better night of sleep using what we call good ‘sleep hygiene’ practices,” Matthew Walker writes in Why We Sleep, “but if you can only adhere to one of these each and every day, make it: going to bed and waking up at the same time of day no matter what. It is perhaps the single most effective way of helping improve your sleep.”

Sleep Is An Act Of Character

I mentioned it above—in the armed forces, they refer to the idea of sleep discipline. In the Persian Gulf in the 1990s, future Admiral James Stavridis had just been given command of a ship for the first time. This occurred at exactly the same time, he noticed, at age 38, that his natural metabolism and his infinitely youthful ability to just gut it out, had begun to decline. You don’t have to be the most self-aware person on the planet to see that you make worse decisions when you’re tired, that you’re less able to work well with others, that you have less command of yourself and your emotions. But it was still a considerable innovation for Stavridis to decide to treat sleep as an equally important part of a functioning warship as its weapons systems.

In response, Stavridis began to monitor the sleep cycles of his crew, moderate their watch duties and encourage naps wherever possible. “Watching our physical health,” he would write later, specifically referring to sleep, “is an act of character and can enormously help with our ability to perform.”

Discover The Life-giving Powers Of The Nap

Anders Ericsson, of the classic ten-thousand-hours study, found that master violinists slept eight and a half hours a night on average and took a nap most days. A friend said of Churchill, “He made in Cuba one discovery which was to prove far more important to his future life than any gain in military experience, the life-giving powers of the siesta.” Naps are restorative, especially as you get older. After a triple-double performance by Lebron James on a Sunday following back-to-back road games in the Midwest and a stop in Phoenix to watch his son play, James was asked if there’s any secret to all the energy he’s been playing with. “Sleep,” LeBron said. “I slept last night from 12 to 8. I got up, ate breakfast, and then I went back to sleep from 8:30 to 12:30.” Teammates joke that Lebron is always either sleeping or playing basketball.

I try to tell this to my kids, who hate napping—one day you will miss this. Trust me. 

Don’t Sleep When You’re Dead (Sleep Or You’ll Die)

The thing I take from Arianna Huffington’s story is that cutting back on sleep not only decreases your quality of life…but it can take your life. People get depressed without sleep. They burn out. They crash their cars. They faint in the bathroom and hit their heads. The philosopher and writer Arthur Schopenhauer used to say that “sleep is the source of all health and energy.” He said it better still on a separate occasion: “Sleep is the interest we have to pay on the capital which is called in at death. The higher the interest rate and the more regularly it is paid, the further the date of redemption is postponed.”

If you want to have a good and long life, sleep now, not later. 

Invest In Your Sleep

When I dropped out of college and moved to LA, I didn’t have enough money to buy a bed. I borrowed an IKEA futon and slept on the floor for almost two months. When I made a little bit of money, I bought the cheapest mattress from the cheapest mattress store and slept on it for almost a decade. I don’t remember when exactly I decided to upgrade but it was long after I could afford otherwise. The point is: If sleep has all these benefits, if it is literally life-saving, then it makes sense to invest in it. Maybe that’s buying a better mattress. Maybe that’s biting the bullet and paying for a layback seat on an international flight. Maybe that’s a sound machine or blackout shades. Figure out what gets you better sleep and consider it a hell of a deal. 

(One part of my sleep routine is the Eight Sleep’s Pod Pro Cover. Actually I should say OUR sleep routine because my wife loves it more than I do…and if she sleeps better, my life is also better.)

P.S. Eight Sleep users fall asleep up to 32% faster, reduce sleep interruptions by up to 40%, and get more restful sleep overall. Eight Sleep’s Pod Pro’s technology makes it easier to sleep through the night, tracks sleep stages, heart rate and HRV, to provide deep health insights. And overtime, it learns from all this data and auto-adjusts to create your optimal sleep environment. It even offers dual-zone temperature control. And I worked out an exclusive deal with Eight Sleep for you all. Go to eightsleep.com/ryan right now to upgrade your sleep experience and get $150 off the Pod Pro Cover!

 

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April 13, 2022by Ryan Holiday
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