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RyanHoliday.net - Meditations on strategy and life
Blog

The 16 Perfectly Reachable Habits That Made Me Who I Am

For 2,130 consecutive games, Lou Gehrig played first base for the New York Yankees—a streak that would stand for five and a half decades. He put up a career .340 batting average. He was a two-time MVP, seven-time All-Star, six-time World Series Champion, Hall of Famer, and the first player ever to have his number retired.

All from a man who wasn’t born an athlete. As a boy, Lou Gehrig was so uncoordinated that a friend joked his body “behaved as if it were drunk.” He made himself into the Iron Horse—day by day, action by action—not with some special gift, but with a handful of perfectly reachable habits. He went to bed early every night. He didn’t drink or smoke. He showed up even when he didn’t feel like it. He never made excuses. He trained on his own. He saved his money. The only thing he ever asked of the staff was a stick of gum on his locker before a game. Two if it was a doubleheader.

Nothing particularly groundbreaking or dramatic. But strung together, day after day, year after year, those small things added up to one of the greatest careers in the history of the sport. And that’s what the path to greatness almost always looks like: small, ordinary actions, repeated for a very long time.

That’s how I’ve tried to build my own life. (It’s also what we built the Habits for Success, Habits for Happiness course around at Daily Stoic. It’s an awesome six-week experience—inspired by the best habits of Marcus Aurelius, Seneca, and Epictetus, as well as my own—that thousands of people have now gone through). 

And so that’s what I wanted to share today—the handful of ordinary habits and practices that, repeated again and again, have had an enormous impact. On my work. On my health. On my happiness. And most of all, on who I am.

– Wake up early. I get up early, between 5:30 or 6am.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. Toni Morrison found she was just more confident in the morning, before the day had exacted its toll and 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. As I said in Discipline is Destiny, this decision we make in the morning, it not only determines how our day will go but it determines who we are.

– Protect the best part of the day. The novelist Philipp Meyer (whose book ​​The Son​​ is an incredible read) ​​told me on the podcast​​, “You have to be very careful about to what (and to whom) you’re giving the best part of your day.” My assistant knows not to schedule anything before mid-morning because early calls and meetings don’t just take time—they sap the energy needed for the essential work. I want to give my best self to my most important things. Everything else can come after. 

– No phone for the first hour. My rule is no phone for at least the first hour of the day. Some days, I don’t touch it until lunch, and on those days I’m happier and more productive.

– Journal. I’ve been keeping a One Line a Day journal for nine years now (you should keep one, they’re amazing). One line. One sentence. What did I think about today? Where did I go? What happened? That’s it. It sounds like nothing—and in a way it is—but the words accumulate. It’s weird how much you don’t remember, even of your own life. Most of what’s in there I’d completely forgotten. Without those pages, it would all be gone. With them, I can flip back and I see the person I was. I can see the person I am becoming. I can see the person I want to be again. I can see mistakes I don’t want to make anymore. I can see all the small things that have added up to who I am. 

– Just a little progress every day. As I wrote about recently, my writing habit was all-or-nothing for a long time—either I wrote a lot of words or I didn’t. Over time, I’ve lowered the stakes: now the question is simply, “Did I make a positive contribution to my writing today?” Sometimes that means writing, sometimes editing, adding, deleting. Sometimes I’m home and it’s in my office, sometimes I’m on the road and it’s on a plane or in a hotel room. Sometimes it’s a big contribution, sometimes it’s a little contribution. 

– Carry a book everywhere. People often assume I’m a speed reader. It’s the most common email I get. They see all the books I recommend every month in my reading newsletter and assume I must have some secret, some trick for reading so fast. The truth is, even though I read hundreds of books each year, I read at a pretty slow pace. In fact, I deliberately read slowly. But I also read all the time. I always carry a book with me. Phone, wallet, keys—and a book. I’ve brought one to the Grammys, NFL games, kids’ practices, restaurants, the DMV, Disneyland, the White House, backstage before talks, and into the waiting room before surgery. Every time I get a second, I crack it open.

– Take a walk. I take a walk twice a day. I don’t think I have ever taken a walk without thinking, after, “I am so glad I did that.” We rescued a dog last year and that’s been the best part. It’s “forced” me to do something I love to do. It’s not about burning calories, but for the philosophical and psychological benefits. As Nietzsche would later say: “It is only ideas gained from walking that have any worth.” 

– Strenuous exercise. I also go for a run or swim just about every day. “We treat the body rigorously,” Seneca said, “so that it’s not disobedient to the mind.” That sounds a little aggressive, because in my experience, the physical practice is actually quite kind to the mind. Some days, it turns it off in a very restorative way. Other days, it lets it wander and work on things. I can’t tell you how many times I’ve thought of a great line or solved an intractable writing problem while running or swimming. Exercise is also an easy win every day. Writing can go poorly, but going on a run or swim always goes well. 

– A simple to-do list. When we were working on ​​​What You’re Made For​​​, the late George Raveling told me that when he became Nike’s Director of International Basketball at 63, having no prior corporate experience, he was overwhelmed by self-doubt. Until a mentor gave him a simple system: “When you leave the office every day, leave a yellow pad in the middle of the desk, and when you come in the morning, write down the three most important things you gotta get done that day in that order. That day, do not do anything else but the first thing on the pad. And if you get the first one, then you go to the second one.” As for me—every day, on a notecard, I write down 5-6 things I want to get done that day. Every day, I cross these off and tear up the card. That’s it. That’s the system. 

– Don’t drink. “Why don’t you drink?” is a question I’ve been asked probably eight thousand times in my life. The real answer is boring: I don’t like the taste. But even if I did, I still wouldn’t. Heraclitus’s line was that “a dry soul is wisest and best.” He’s right. Have you ever done anything you’re really proud of while drinking? Is anyone their best selves while drunk? Of course not.

– Don’t drink calories. This is one I got from Tim Ferriss. Along with not drinking alcohol, I don’t drink soda, smoothies, juice, milk, anything. It’s just a simple way to help keep your diet on track.

– Focus on process, not goals. As I wrote about recently, I don’t have goals. When I write, I don’t focus on finishing books—that would be overwhelming. Instead, I focus on my notecard system and writing for a couple hours every day. The books emerge from that process naturally, over time.

– Think about death. Shakespeare said that every third thought should be of our grave. Perhaps that’s too much. One thought per day is plenty. I keep a coin in my pocket to remind me of this and touch it at least once a day. Death doesn’t make life pointless but rather purposeful. And fortunately, we don’t have to nearly die to tap into this.

– Review the day. “When the light has been removed and my wife has fallen silent,” Seneca wrote, “I examine my entire day and go back over what I’ve done and said, hiding nothing from myself, passing nothing by.” He’d ask himself: What bad habits did I cure? What temptations did I resist? In what specific way am I now better than I was yesterday? I spend some time every night on my own version. Did I follow my plans for the day? Was I prepared enough? What could I do better? What have I learned that will help me tomorrow? These simple questions make an enormous impact. So I spend some time every night answering them.

– Sleep with the phone in another room. Ben Sasse used to give his young staffers old-school alarm clocks—not because he wanted to make sure they were on time for work, but so they wouldn’t have an excuse to sleep with their phone on the nightstand. If your alarm isn’t your phone, your phone can go in the other room. And if your phone is in the other room, you can’t check it at night. Which means I won’t know if a text or an email comes in. I won’t be tempted to scroll. I’ll have to lie there with my own thoughts, read a book, or maybe even go to sleep at a reasonable time.

– Go the F*ck to Sleep! I follow the advice of a book I love to read to my kids: Go the F*ck to Sleep! All the other habits and practices listed here become irrelevant if I don’t have the energy and clarity to do them. 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. Knowing this, I guard my sleep carefully. I try to get my 7-8 hours of sleep every night.

July 16, 2026by Ryan Holiday
Blog

This Is Always Worth All The Trouble (Or So I Tell Myself)

There are a million good reasons not to travel.

I woke up with a bunch of them this morning. 

I was exhausted. My kids were fighting. My wife has been sick. It was ungodly hot—literally the hottest Europe has ever been. My routine is out the window. So is any sense of a budget. Our suitcases are already full of knick-nacks and crap we don’t need and there’s quite a bit of trip left. The car that was supposed to pick us up for our tour is late. 

But we’re in Rome. 

It’s all worth it…or so I tell myself.

Even though travel can be expensive, stressful, and frustrating. Even though it tests your patience. Even though things go wrong. Even though you know that when you get home, you’ll be behind on everything.

Still, it’s worth it. 

It has always been worth it.  

For all their warnings against escapism, the Stoics traveled widely—in an age when travel was far slower, harder, and more dangerous. 

Unlike his stepfather Antoninus, who never left Italy, Marcus Aurelius was on the road a lot as emperor. It wasn’t always pleasant. But it undoubtedly influenced his philosophy and his view of the world. He could have sent someone else to inspect the troops on his behalf, but he chose to go. When the calls of duty and the road converged, he went. Seneca was born in Corduba, Spain (modern Córdoba), moved to Rome, and in addition to his exile in Corsica, lived for nearly a decade in Egypt. Posidonius (a key figure in Middle Stoicism) worked and lived in many places throughout his long life—Syria, Athens, Rome, and Rhodes—and traveled almost the entirety of the known world. After completing his studies under Posidonius, Athenodorus traveled widely as a lecturer, reaching Petra, Egypt, and other major Mediterranean cities before becoming young Octavian’s teacher in Apollonia, on the coast of modern Albania.

These were critical experiences for them. Then, and now, hitting the road was a source of wisdom. It shaped their philosophy. It enlarged their view of the world. It opened their eyes to new lands, new customs, new perspectives.

“Travel is fatal to prejudice, bigotry, and narrow-mindedness,” Mark Twain famously wrote, “and many of our people need it sorely on these accounts.” 

This was true of America in the 19th and 20th centuries, and it was true in Rome in the first century. Marcus Aurelius’ passages in Meditations which reference being a citizen of the world were almost certainly shaped by the people he met in Athens and Tarsus and Alexandria (and of course the people he met in Rome who had traveled there from far away). 

Every culture thinks its norms are, well, normal. One of my favorite examples of this is the criticism I get that by talking about politics I am “upsetting half my audience.” It’s the most American thing in the world to assume that the world is as evenly divided as America is. (Shocker, it’s not!) 

Only travel can shake us from this ethnocentrism, awakening us to the plain fact that our way of life is but one of many. In our travels, we meet people who care about different things, wear different clothes, tell different stories, eat different foods, speak different languages. 

When he traveled, Montaigne sucked up everything he saw like a vacuum, avoiding much in the way of plans, leaving himself open to chance encounters and experiences. Like the time he came across men leading two ostriches on leashes as a present for a duke. He stopped in at every church he could find, taking in their various practices like an anthropologist.

When the New World was discovered—basically in his lifetime—Montaigne did not think the people who lived there were savages. From his travels, he understood that every distant land has its own culture and beliefs—and that our customs would seem just as barbaric to them. Not that he defended the “horrible barbarity” of cannibalism. What struck him was that “while judging correctly of their wrong-doings we should be so blind to our own.” Did the cannibals draw and quarter each other? Commit atrocities? Accuse each other of black magic? Who was actually the barbarian?

Perhaps it was a lesson he first absorbed from his extensive reading of Herodotus, our first great historian and travel writer, who traveled thousands over the course of his life—from Persia to Athens to Italy, Libya, Babylonia, Byzantium, and the Black Sea. Above all, he delighted in getting inside the nomos of each place—the people’s customs, and the ways they differed from his own. He loved to tell the story about a small sect in India that ate a small piece of their dead as part of a religious ritual. Obscene! Disgusting! But how did these people react when told that Greeks burned their dead at the funeral pyre? An outrage! A sacrilege!

Me and Herodotus in the Palazzo Massimo

The world is very big. The place you call home is only one small corner of it. There is wisdom on the other side of the hill, wisdom in the experiences that only the road can give you, wisdom in learning how other people live and why they live that way.

It’s easy to be comfortable where you are. To tell yourself that travel isn’t worth all the hassle. To think of it as a luxury, an indulgence, a needless extravagance. But it isn’t. It’s essential. “I was never a fan of people who don’t leave home,” the well-traveled Joan Didion once wrote. “It just seems like part of your duty in life.”

But leaving home doesn’t have to mean going far. It doesn’t have to mean spending lots of money on some exotic trip to the other side of the world. I remember talking to a waitress in Natchez, Mississippi once who told me she had never been to Vicksburg (a little over an hour away!). Growing up in the suburbs of Sacramento, I was lucky my parents took us on trips to Europe and China and Canada and Mexico, but I BARELY ever went to downtown Sacramento. Or even San Francisco. I only discovered the fullness of those cities as an adult. 

Don’t tell yourself you’ll do it later. When you’re older. When the kids are older. When things settle down. When you have more money. When it’s more convenient. That misses the point. You don’t need the benefits of travel someday, when your life is perfectly arranged for it. You need them now.

So hit the road! Travel to the well-known places and the little seen. Travel by boat and by car and by train and by plane and by foot. Read the signs. Struggle with the language barrier. See things from the other side of the road. Eat the food. Go to the museums. Sit at sidewalk cafes. See the ancient hieroglyphs and notice graffiti on city streets. See the cemeteries. Visit the battlefields. Listen to people chatter. Learn. Explore. Be curious. Ask questions. Carry a notebook. Write down everything you see and feel and think.

See your own country as a tourist. Live abroad like a local. Every building, every person has a story. Think of what they witnessed. Think of who stood where you are standing. Think of what was here before any of this was here. Think of what people used to think here, what they were afraid of, what they hoped for, what they believed.

Let things go wrong (and they will!). These experiences teach as much as anything else. Last summer, I spent 27 days in Greece with my family, covering some 3,000 kilometers between Athens, Olympia, Ithaca, Delphi, Thermopylae, Mount Olympus, Marathon, and Cape Sounio. We were in a Chinese rental car that was far too big for tiny ancient streets. We got a flat tire at the top of Mount Olympus. I was stung by a jellyfish near Thermopylae. We bumped into friends I hadn’t seen since high school. We got ripped off. On the last day, a bee stung me in the back of the throat and I almost died. Oh, and somewhere in between there, I got myself a bad case of sunstroke. 

But that’s what travel is supposed to be. Travel is an adventure. Travel is pushing your limits. Travel is trying new things. Travel is learning that most problems can be solved, most setbacks can be survived, and most of what goes wrong can be figured out. 

You don’t have to be gone for long. You don’t have to spend a fortune. You don’t have to see the whole world to become a worldly person.

But you have to check out what’s on the other side of the hill a couple times.

You have to expose yourself to different places, different people, different perspectives.

You have to hit the road.

It will be disruptive. Your patience will be tested. Things will go wrong.

And it will all be worth it.

July 2, 2026by Ryan Holiday

“If you only read the books that everyone else is reading, you can only think what everyone else is thinking.” - Murakami

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