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.

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!