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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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!

I’ve done some crazy things in my life, but as I’ve said, the absolute craziest was deciding to open a bookstore. Running a small business is always difficult, running a small business during a pandemic is damn near impossible but a small town book store in rural Texas? 

But here we are, a year later, not just still standing but doing great! 

We’ve learned a lot…about business, about books, and about ourselves. 

I made a YouTube video about the experience, but I wanted to expand it here into a fuller explanation of all the lessons that The Painted Porch has taught me. I share them here so you can get something too—and perhaps learn a little from my experiences and hopefully go create something cool of your own out of it. Here are 29 lessons from the first 12 months of owning The Painted Porch. 

– It always takes longer than you think it’s going to take. That’s Hofstadter’s law. From the moment my wife suggested we open a small-town bookstore, everything has taken longer and been harder than we expected. If you can’t pass the marshmallow test of delaying gratification and deferring things into the future, you’re just going to get crushed. 

– For most of my life as an author and entre­preneur, my work has been digital. Close to half of the sales of my books are audiobooks and ebooks. Every morning, I send out the Daily Stoic and Daily Dad emails to over 500,000 people. I put out a podcast that’s had 80 million downloads. As satisfying as it is to reach large numbers of people through the enormous scale of the internet, there is even more satisfaction in doing something in real life, for real people, even at a much much smaller level. Every time I walk by or to the bookstore, I think, Wow, I made that. 

– I think one of the best decisions we made was making our book tower. It’s 20 feet tall and made of some 2000 books, 4000 nails, and 40 gallons of glue. It was not cheap to do. It was not easy to do. It took forever. We had to solve all sorts of logistical problems to make it work. But it’s also probably one of the single best marketing and business decisions we made in the whole store. Because it’s the number one thing that people come into the store to take pictures of. 

– You want to have a unique proposition. You want to have something that only you could do. Most bookstores have thousands and thousands of books. But what we decided here was that we’d have only a couple hundred books, only my absolute favorite books, only the books I put in my Reading List Email. It would only be those books. So not only did this make it cheaper and easier to run the bookstore, it makes us stand out. 

– There’s this great story of when Jeff Bezos had the idea for Amazon. He was working on Wall Street at the time. He and his boss go for a walk in Central Park and after he tells him his idea, his boss says, “that sounds like a great idea for someone who doesn’t have a job.” Meaning that somebody else should do it, not Bezos. If there’s something crazy that you’re thinking about doing, maybe you should get serious about actually doing it. On the other side of the risk and the crazy leap can be something that changes your life, that changes your community, that changes the world.

– Doing something cool means risk…but just because you take a big risk doesn’t mean there aren’t lots of little ways to take risk off the table. My office is above the bookstore. I rent part of the building out to another business, etc. 

– There are lots of easier ways to make money than a physical bookstore in 2022…so everyday I try to remind myself this project was not about making lots of money. Remembering why you did something and how you measure success helps you calibrate your decisions properly. I’m happy enough to be putting books out in the world, making this community better, having a physical space, challenging myself, etc…as long as I don’t lose lots of money, that’s a win. 

– Start small. The problem is when you have really high standards, when you expect a lot of yourself, it’s hard to be comfortable with something that’s kind of crappy or mediocre or not all the way there. But there’s a reason most tech start ups think in terms of a minimum viable product. 

– Related to that there’s a great Hemingway line—we actually have a shirt with it, and I have a print of it on my wall—it’s one of my all-time favorite quotes: the first draft of everything is shit. I love how The Painted Porch is now, but it took weeks and months to get it to where it is. It’s been a continual process of improvement and growth and making changes.

– Lengthen your timeline. I mentioned Hofsteader’s Law above—it was important to remind ourselves many times that the building we were in was nearly 150 years old. It can be very easy on a project to get caught up in the immediacy of what’s in front of you…but you miss the big picture and you miss the reality that most things that work are set up to work for a long time. We sell books in our store that were written 2,500 years ago! Who cares if the project took 13 months longer to open than we thought?

– As Zeno said, books are a way to have conversations with the dead. You can learn from people who came before you. They can also inspire and reassure you. Some books I leaned on often throughout this were The War of Art by Steven Pressfield, Meditations by Marcus Aurelius, and A Calendar of Wisdom by Leo Tolstoy.

– One of the things I did while I was kicking around the idea is I looked up how expensive it is to start a bookstore. Search results said it was hundreds and hundreds of thousands of dollars—way more expensive than I was interested in. But then I wanted to question whether that number was real. So then I went and looked up how expensive it was to start an ecommerce business—something like Daily Stoic. Search results said it was hundreds of thousands of dollars more than I’d spent to start Daily Stoic. That was really helpful—to learn, oh, these people don’t really know what they’re talking about. Or that there’s a cheaper way, a different way to do it. You don’t have to do it the way that everyone else does it.

– Steal like an artist (also a great book we carry). We got the idea for the bookshelves in our store at someone’s house for a toddler’s birthday party. They had built them themselves, we took a picture and had our contractor do his own version. The book tower was roughly inspired by The Last Bookstore. Even the idea to carry fewer titles and put them face out was partly inspired by Amazon’s physical bookstores. Take from many influences and make them your own. 

– One of my favorite parts of the whole experience has been watching my wife work her magic. Not only was the original idea to do the store hers, but almost all the big design ideas were hers too. We have very different styles of working but collaborating on this challenged me to see the wisdom in her approach on a humblingly regular basis. 

– When you get criticism, when you get information, when you get facts—and of course you have to look for those things—you have to take them with a grain of salt. You have to put them up to the test, as the Stoics say. You have to question some of the assumptions out there. You might just find, as we did, that instead of something being way too expensive, it is actually doable for you to do it.

– Think of it as an experiment. When I was thinking about opening The Painted Porch, I asked Tim Ferriss for advice. “Think about it as an experiment,” he said. “How are you going to know if it’s something you want to do if you haven’t tried doing it?” The decision to see it as an experiment, not as a permanent life choice, was so freeing. It allowed me to go into it knowing that I was going to commit to it for the next two years, and then, I can reassess, I can change my mind.

– Confidence is earned. People talk about trusting their gut. But that’s something you have to earn. I talk about this in Ego is the Enemy—there’s a difference between confidence and ego. Ego thinks, whatever I want to do, of course I’m going to be successful. Confidence is something you earn, something you earn over time. It’s something you earn through having an idea and bringing it into reality. It’s learning what you’re capable of, learning what’s possible, learning why you do deserve to trust yourself. Confidence is on the other side of having done a scary thing, a thing that a lot of people said wasn’t a good idea.

– In Letters From A Stoic, Seneca says he pitied the person who’s never gone through adversity, who’s never done anything difficult. Because they don’t know what they’re capable of. Well…cue March 2020.

– Help yourself by helping others. When I first started my Reading List Email in 2008, the idea was that I wanted to celebrate other people’s works. To me, the bookstore is an extension of the idea of celebrating other people’s work. And when you do that, when you create value for people, when you’re generally a positive force in your industry, in your space, you develop a reputation. People want to support you. People want to help you.

– Robert Greene’s metaphor for mastery (if you haven’t read Mastery, you must) is being on the inside of something. When we start a new sport, when we get a new job, when we approach a field we haven’t yet studied, we are on the outside of. But as we put in the work, as we familiarize ourselves with every component, as we develop our intuitive field, we eventually make our way to this inside. This is a metaphor I think about constantly with the bookstore.

– Permission assets are everything. All my success as a writer, right down to this bookstore, has been rooted in the email lists and social media accounts I have built. When you have direct access to people who like what you do, everything is more affordable and more scalable. When you don’t? Everything is harder and requires so much more luck. 

– Just do the right thing…the rest doesn’t matter. That’s what Marcus Aurelius writes in Meditations. We delayed opening during the worst days of COVID—we didn’t need to, so why contribute to the problem? We paid people to work remotely instead. We kept up safety protocols even after the state of Texas washed its hands of its responsibilities last year. We did it even though people got mad at us for it, even though it probably cost us business. My conscience is clean and that’s what counts. Keeping your community and your staff safe is good for business in the long run anyway. 

– If it makes you a worse person (parent, neighbor, writer, whatever), it’s not success. On a note to myself when we were opening the bookstore in the middle of the pandemic, I wrote, “2020 is a test: will it make you a better person or a worse person?” That was the test that I reminded myself of over and over again: will this make you a better person or a worse person? If starting a business makes you a worse person—if it stresses you out, if it tears your relationships apart, if it makes you bitter or frustrated with people—then it doesn’t matter how much money it makes or external praise it receives. It’s not successful.

– As we were going through it, my wife and I asked ourselves, what does success look like? And we decided that success was going to be: becoming more community minded, becoming more responsible, becoming better organized, having more fun, making a positive contribution.

– Physical experiences matter more in a digital world. If people wanted a book cheaply, they’d buy it online. There has to be a reason people would drive out and come to your business.  We made a lot of our design and marketing decisions around that idea.  

– It would be wonderful of course if marketing didn’t have to exist. If things could be bare-boned. If presentation and packaging didn’t matter. That’s just not how life works—never has and it never will. You have to do interesting stuff. You have to make remarkable things, as Seth Godin writes in Purple Cow, you have to do remarkable marketing. Do stuff that commands attention. Draw attention like a magnet. These things cannot be underestimated.

– COVID has been tough. Even as I was working on this piece, we had to close because people got sick, even after all our precautions and we couldn’t stay open. That was expensive and it was scary for everyone. But we took it one day at a time, we adapted, we adjusted, we figured it out. Which is all you can do. .

– In The Obstacle is the Way, I quote this Haitian proverb that I like: behind mountains are more mountains. That’s just how life is. You don’t overcome one obstacle, you don’t get through the first year of your business, and then suddenly, you’re magically done with obstacles. No, that’s not how life works. Life is one obstacle after another. You just have to keep going. 

– I mentioned Austin Kleon’s book Steal Like An Artist earlier but his book Keep Going was even more relevant to this journey. 

I happened to be writing Courage is Calling during most of the crazy period of putting this book store together. Obviously, starting a small business is not the same as running into a burning building or onto a battlefield, but one thing you can’t escape noticing when you read history or biography is just how badly we need people to step up, to put themselves out there, to pursue their crazy ideas. All of human progress—big and small—depends on that. 

If you’re thinking of doing something, if you feel called to do something…well, maybe you should do it. Just remember to…

• • Start small.
  • Be patient.
  • Think of it as an experiment.
  • Do it the way only you could do it. 
  • Find ways to take risk off the table.
  • Define what success means to you.
  • Question some of the assumptions out there.
  • See adversity as an opportunity to find out what you are capable of.
  • Keep going—behind mountains are more mountains.

Anyway, come visit us on Main St. in Bastrop sometime…or support the store online at thepaintedporch.com! Some of the most popular books in the store are Empire of the Summer Moon by S.C. Gwynne, The Library Book by Susan Orlean, and The Tiger: A True Story of Vengeance and Survival by John Vaillant. We’ve also had many of my favorite authors stop by and sign copiesof their books, such as: The 48 Laws of Power by Robert Greene, The Subtle Art of Not Giving a F*ck by Mark Manson, From Strength to Strength by Arthur Brooks, and Finding Ultra by Rich Roll. If you buy from those links, your books will be shipped from us here in Bastrop, Texas!