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RyanHoliday.net - Meditations on strategy and life
Blog

These Are Leadership Ideas I Try To Apply Every Day

Coach Pete Carroll has said that another disappointing season with the New England Patriots—some 15 years into his career—it struck him that he didn’t actually have a coaching philosophy. He was mostly winging it.

Inspired by John Wooden’s “Pyramid of Success” philosophy, Carroll got to work filing binders with notes, compiling, defining, and codifying what would become known as his “Win Forever” philosophy—the winning actions and mindsets he aims to instill in his staff and players. It was a transformative decision: he went on to win two national championships and then a Super Bowl with the Seattle Seahawks.

Now, when Carroll gives talks, he often opens with a simple question: What’s your philosophy? I once asked him about it, and he told me it’s shocking how many people don’t have an answer. There are many CEOs and generals and investors and coaches at the highest levels who reveal, accidentally, that they have just been winging it.

Although I always saw myself as a writer and wanted that to be my life, I found myself running the marketing department of a publicly traded company by 21. I started my own company in 2012, and given how the world works now, few writers can just be writers. We now have a team of roughly 20 employees across ​Daily Stoic​ and ​The Painted Porch​. Which means I’ve had to develop a leadership philosophy to try to get the best out of the people who are part of it. You can’t make every decision for people, so it’s essential to establish the principles and rules by which others make decisions and operate on a day-to-day basis.

While this post isn’t a totally comprehensive breakdown of my philosophy (if you want that, ​check out The Daily Stoic Leadership Challenge​), these are the core tenets—the maxims, rules, and reminders the people who work for me hear most often.

Sense of urgency. At The Daily Stoic offices above The Painted Porch, I hung up a sign that says, “​A Sense of Urgency​.” It’s something I cribbed from the kitchens of Thomas Keller, the creator of Per Se, one of the best restaurants in the world. A sense of urgency—that’s what a great chef, a great service staff, a great organization has. While in my personal life I ​may need to work on slowing down a bit​—I’m a ‘sense of urgency’ guy, always have been—I’d say most people could use a little speeding up. A couple of weeks ago, a shipment of books came in on a Friday afternoon. I heard someone on the staff say, “We’ll unpack those tomorrow.” I’m glad I heard it because I had to stop them and explain that, unless the books in those boxes were opened and the orders waiting on them were fulfilled (in time for the morning mail pickup on Saturday), they would not even begin traveling in the customer’s direction until Monday afternoon. So what seemed like a little delay until the next morning was really like a 72-hour delay. Every small delay or shortcut has second-, third-, and fourth-order consequences. That’s why it’s important—whether you’re packing boxes, replying to emails, or making big strategic calls—to think a step or two ahead. Don’t procrastinate. Do it now. Do it with urgency.

Slow down…to go faster. Yes, it’s important to have a sense of urgency. But there’s a difference between urgency and rushing, hurrying, going quickly for the sole sake of speed. There is an old Latin expression that I think captures the balance here nicely: Festina Lente, which means, Make haste slowly. A sense of urgency…with a purpose. Energy plus moderation. Measured exertion. Eagerness, with control. It is about getting things done, properly and consistently. They like to say in the military that slow is smooth and smooth is fast.

Start the clock. One of the things I say all the time is ​“Have we started the clock on this?”​ When someone tells me that it’s going to take six weeks for our bindery to make another run of the leatherbound Daily Stoic, I want to “start the clock” as soon as possible. I don’t want to add days or weeks to that process by being indecisive about how many to order or by procrastinating on finalizing the order or by being slow in processing an invoice. We don’t control how long it takes other people to do stuff, but we control whether we waste time, whether we are inefficient on our end…The project is going to take six months? Start the clock. You’re going to need a reply from someone else? Start the clock (by sending the email). It will likely take a while for the bid to come back? Start the clock (by requesting it). It’s going to take 40 years for your retirement accounts to compound with enough interest to retire? Start the clock (by making the deposits). It’s going to take 10,000 hours to master something? Start the clock (by doing the work and the study).

Don’t touch paper twice. That’s a great rule from the productivity guru David Allen. If you look at an email, begin to edit a piece of content, open a text, whatever—complete the task then and there. This has been driving me nuts on a home remodel we’re doing. The amount of decisions that have come to us more than once is insane. Because the contractor forgets things, because it turns out they didn’t give us the right parameters the first time, because they were asking before we were ready. But people do this all the time! They have bad processes that make them do more work than they need to.

What’s taking up a lot of your time? One question I regularly ask my employees—and myself—is: What’s eating your time? Sometimes this is just life but sometimes, it’s unnecessary. On one of our weekly calls not too long ago, I could tell my video producer was feeling overwhelmed. I asked, what’s taking up a lot of your time? Animations. He said it was taking hours to produce just two minutes of animated content for our Daily Stoic videos (which a previous editor had often included in our videos and become part of the style). I like animations…but not that much! So we cut way back on them and everything got better. Unless you want your boss to micromanage you, you can help them by flagging things that if they knew about they would help you fix. (And by the way, AI has now helped us do these animations faster).

Don’t punish people for improvements. Sometimes people are afraid to tell you about inefficiencies or even potential improvements because they are worried it will turn out badly for them. That you’ll get mad. Or you’ll take away responsibilities or find someone else to do it cheaper. I try to reiterate all the time: I not only won’t punish you for this, I will reward you. If you help save us money–by reducing an unnecessary vendor or service–I’ll give you a piece of it. If you find out that something in your role no longer has a positive ROI or isn’t worth doing, we’ll get rid of it and find something different and better for you to do. If you find a way to work faster with AI, I’ll celebrate that. Your job is to make the company better, not to do your ‘job’ as it was originally defined.

Make a positive contribution every day. Compound interest is one of the most powerful forces on earth. And you can apply that to your own work. People sometimes ask how I write the Daily Stoic email every morning, which of course, I don’t. I write one or two every day, constantly making small deposits to the bank of emails. Over time, that compounds—we have a Google Doc we call “UNSENT,” which, as I type this, is 217 pages long with emails ready to go. Little things add up. The line from Zeno was that big things are realized by small steps. That’s what I try to instill in my team: every day, make a positive contribution. Most of all, I try to show this with my own writing habits.

Be there when they’re losing, not when they’re winning. When we were working on ​​​What You’re Made For​​​, George Raveling told me that when he got the head coaching job at Washington State, the athletic director told him, “I’ll always be there when you’re losing,” he said. “I’ll never be there when you’re winning.” I loved that. I find that I talk to my team the most when they’re struggling—when something’s broken, off-track, or unclear—not when everything’s going well. That’s the job: to help people solve problems, to help them get unstuck. If someone needs constant reassurance or regular praise to stay motivated, they usually don’t last long here. I’m reminded of a time I called Dov Charney, founder of American Apparel, about some little success I’d had on some project. He was very busy and frustrated that I’d interrupted, but politely, he said, “Ryan, you are calling me to tell me that you did your job.”

Don’t repeat the same mistake. On the one hand, I’ve always loved the story of IBM CEO Tom Watson supposedly calling an executive into his office after his venture lost $10 million. The man assumed he was being fired. “Fired?” Watson told him, “Hell, I spent $10 million educating you. I just want to be sure you learned the right lessons.” But on the other hand, the thing that frustrates me the most—and the only reason I’ve ever fired someone—is when they keep repeating the same mistakes. If you learn from your failures, great. But if you’re just stuck in a loop, not applying the lessons, it’s not going to work.

Why is it being done that way? One day I noticed our team was packing shipments in a pretty inefficient way. I asked why. The answer? That’s how so-and-so showed me when I started. No one had questioned it since. This happens all the time—in businesses, on teams, in life. People inherit a process, follow it out of habit, and never stop to ask: Is this the best way? Does this still make sense? The most useful question in any system is often the simplest: Why are we doing it like this? This is especially important to ask of tasks that eat away at time better spent on something else.

Steal like an artist. (This is also ​a great book we carry​ at The Painted Porch.) At some point, I realized many of our best ideas were inspired by others. ​The book tower​—​as I’ve written​, one of the single best marketing and business decisions we made in the whole store—was partly inspired by a cool floor-to-ceiling tower of books about Abraham Lincoln in the museum attached to Ford’s Theater in DC. Some of our top-performing ​reels on Instagram​ were inspired by other creators. So now, at the end of every weekly staff meeting, we go around and share one idea we’ve seen out in the world—on social media, on podcasts, on YouTube, in movies and documentaries, at other small businesses—and talk about how we might do our own version of it. Not copying, but adapting. Remixing. Borrowing what works and making it ours.

I’m leaving this with you. Like a lot of men of my generation, I’ve learned about this concept of “mental load” in relationships (the way, unthinkingly, a lot of responsibilities, emotional obligations and tasks are placed on women). My leadership philosophy is that when I give you a task, that’s your task. Your job is to handle it and be in charge of it. If I have to follow up with you, if I have to push you to get started, if I have to check your work, then I may as well have done it myself. If you are coming to me with problems (as opposed to solutions) or, when you are explaining something to me, not explaining your assumptions, you are putting it back on my plate. In a successful working relationship, I should be able to have an idea, go to the right person with it, and after I explain it say, “I’m leaving it with you.”

Respect boundaries. As a leader, you have to understand that your decisions and actions have consequences for people, not all of which are immediately obvious. But you have to think about that. For example, I sometimes have to reiterate that just because I am emailing late at night or on the weekend doesn’t mean I expect a response right then. And for this reason, I’ve gotten better at scheduling emails. But the broader point is that as a boss you have to realize your actions, however seemingly small, carry weight. You have the power to blow up someone’s day or evening or weekend. Try not to do that. Try to be mindful of other people’s time and headspace.

Kids are not a distraction from your work. They are your work. I bring my kids to the office. I talk about them in meetings. When they’re a fan of the guest, I ​let them pop into podcast recordings and ask questions​. And I encourage others to do the same. If you need to take paternity or maternity leave—take it. If you want to bring your kid to work—bring them. If you have to duck out for a school pickup—go. Especially as a father, I’ve tried to model this. I don’t want to treat my kids like a separate life I live outside of work, and I don’t want the people who work for me to feel like they have to either. Being a parent is not a liability or a distraction—​it’s one of the most meaningful things a person can do​. Our policies, our expectations, and our culture should reflect that.

Do things only we can do. Something that’s happened with ​Daily Stoic​ over the years is as it has grown, so has the number of copycats. And so we’re constantly asking, what can only we do? With the bookstore, for example, we’re lucky to have authors constantly passing through to record the podcast. While they’re here, they sign books. ​Sometimes we do live events with them​. Those books, those experiences—you can’t get them anywhere else. ​This has always been good advice​, but with these AI tools making it easier and easier to copy and replicate and reproduce, it’s more important than ever to find and focus on the things only you can do.

Do the hard things first. The novelist Philipp Meyer​ (whose book ​​​The Son​​​ is an incredible read) ​told me on the Daily Stoic podcast​, “You have to be very careful about to what (and to whom) you’re giving the best part of your day.” A corollary to this: the poet and pacifist William Stafford had a great daily rule: “Do the hard things first.” Well-intentioned plans fall apart as the day progresses. Our willpower evaporates. The world makes its demands. My assistant knows not to schedule anything before mid-morning because early calls and meetings don’t just take time—they sap the energy I need to do the hard work. I want to give my best self to my most difficult things. And I encourage my team to do the same: protect the early part of the day, guard your energy, and use it on what matters most.

It’s not a principle until it costs you something. There are lots of ways to make money—many of them easier and more lucrative than ​writing about an obscure school of ancient philosophy​ or ​opening a small-town bookstore in the middle of a pandemic​. Of course, it still has to make money, but not being motivated solely by profit gives me a certain freedom: the ability to act with a heart and conscience, to take stands, to say what I think needs to be said. Every time I write something even mildly political in a ​Daily Stoic email​, we lose a disproportionate number of subscribers. I get lots of angry emails. People accuse me of having changed or they say the Stoics would be disappointed. I sometimes remind them–if not ​something about how all of the Stoics were active in politics and explicitly said the philosopher is obligated to participate in politics​–that I didn’t build an audience to not write or say what I think. Or when the team alerts me to the number of followers we lost after I said something political on social media, I tell them the same. And besides, how successful are you really if you censor yourself because you’re afraid it will cost you?

Help people get to where they want to go. It’s very unlikely that anyone you hire is being hired for their dream job. They are not signing up for lifetime employment. No, this job is a waystation. I don’t think we should pretend otherwise. ​In fact, we should embrace it​. When Tim Ferriss was looking for someone to run his podcast and email a few years ago, he asked me if he could hire Hristo Vassilev, who was then my research assistant. You know what I said? I said “Of course.” And he’s been Tim’s right hand ever since. Brent Underwood, who started as my intern more than a decade ago at the marketing company I was building, has gone on to write ​a bestselling book​ and build a hugely popular ​YouTube channel​about the ghost town he owns. My last assistant currently runs a large nonprofit. To be clear, I’ve had some assistants and employees that didn’t work out. But I think I’ve got a pretty good “coaching tree” so far. In sports, a coach’s success isn’t just defined by wins and losses, but by their “coaching tree”—the players, coaches, and executives that they discovered and mentored who’ve gone on to do great things in their own careers. It’s a concept I think about a lot and ended up doing a chapter on it in ​Right Thing, Right Now​ because it deserves to be recognized outside of sports. It’s just a wonderful way to measure a life. Your job as a leader is to have a large coaching tree. Almost no one you hire is going to be a lifer. Chances are, you are not offering them their dream job, but you could be the one who helps them get closer to that dream job.

Don’t try to map out the whole game. Along these lines, a few years ago, during our year-end one-on-one, I asked my current researcher, Billy Oppenheimer, where he wanted to go. If you’re still working for me in this capacity in five years, I said, we both screwed up. The way to get the most out of this kind of relationship is if I have some idea of where you want to go. Then I can try to help you get there. He told me he wanted to be a writer but was just waiting to know for certain what I wanted to write about. After he described some complicated way in which he was privately writing stuff and looking for patterns to determine what to write about publicly, I told him, Just start. You’re trying to map out the whole 9 innings. Just throw the first pitch. Soon after, ​he started a great newsletter I read every Sunday​, which led to him now also working for Rick Rubin and signing his first book deal last year.

So yes, it’s critical to define the principles and rules you live and lead by. It’s critical to have an answer to that question, What’s your philosophy?

But as you get to work figuring out yours, keep in mind, you’re better off starting imperfectly than being paralyzed by the delusion of perfection. As they say, another way to spell “perfectionism” is p-a-r-a-l-y-s-i-s.

Don’t try to map out the whole game.

Just throw the first pitch.

Just start.

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April 16, 2025by Ryan Holiday
Blog

4 Years Of Lessons From Running My Own Bookstore

It was a crazy idea from the start. 

My wife and I were sitting at a cafe in Bastrop, TX and we spotted an empty storefront, a building that’s part of the National Register of Historic Places.

“You know what would be amazing there?” my wife said. “A bookstore.”

We started construction the first week of March 2020. 

But somehow, we didn’t lose all our money. It didn’t blow up our marriage. It’s actually been a great experience and, even more surprising, a pretty good business too. 

Four years in, one of the first things people want to know is how our bookstore The Painted Porch is doing, whether it’s a success. I’d say so. I’ve certainly learned a lot along the way, both about business and life, as well as publishing and people and myself. 

Here are some of those lessons: 

Counterprogramming is key. So yeah, opening a physical bookstore in 2020 seemed crazy. Not just to me—everyone said so. Retail was shifting online, books were becoming digital, the pandemic was raging, bookstores were closing—not opening. But that’s exactly why it worked. It was crazy because no one else was doing it. It stands out. It’s different. 

Have more than one way to win. This was a great piece of advice I got from Allison Hill, who owns Vroman’s and Book Soup in Los Angeles: most bookstores only survive if they’re multipurpose spaces. The Painted Porch isn’t just a bookstore—it’s my office, my employees’ office, the place where we record podcasts and film YouTube videos. So if nobody comes in and buys books, we’re not necessarily losing money.  At the same time, it probably also wouldn’t have made sense to build out this level of podcast studio or even a writing office by itself either. So multi-use allows you to do more than you ordinarily would—across the board.

Resist the pressure to scale. At least once a week, someone asks us if we’re going to open a second location. And at least three struggling bookstores have reached out about us acquiring them. The answer is a polite no. “Do Not Go Past The Mark You Aimed For” is one of the most important laws in The 48 Laws of Power. Know when you’ve won. Know what enough is. Know your limits. 

Have a unique proposition. Most bookstores carry thousands of titles. The best one in Austin, BookPeople, stocks over 100,000. We carry about 1,000. It was one of the best decisions we made—both personally and professionally. We only carry books we love. Not only did this make it cheaper and easier to run the bookstore, it makes us stand out. It gives people a reason to come in. If people want a specific book, they go to a certain trillion-dollar e-commerce behemoth. If people want to discover new books and have a unique experience, they come to us. We are the only bookstore in the world with our selection. Again, counterprogramming. 

Create spectacles. Before we opened the store, I was in Bucharest, Romania for a talk. My host took me into a local bookstore that had an enormous globe hanging from the ceiling. I watched as customer after customer came in to take pictures beneath it, before checking out with books. For me, one of the key pieces of the puzzle was figuring out what kind of marquee feature we could add that would make coming to the store an experience. I recalled a particularly cool floor to ceiling tower of books about Abraham Lincoln in the museum attached to Ford’s Theater in DC. 

This inspired our now infamous book tower, which I designed to be built on top of an old, broken fireplace in the building. It’s 20 feet tall and made of some 2,000 books, 4,000 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. Invariably, almost every customer that comes in takes a picture of it—plenty more come in because they heard about it and wanted to see it.

Pass it on and pay it forward. I’m proud of the books I’ve championed over the years—of paying forward what inspired me, like the Gregory Hays translation of Meditations (I loved it so much I even put out my own edition). I love looking around The Painted Porch and seeing books you don’t often see in other stores. Just last year, the publisher of Ann Roe’s Pontius Pilate told us they had to do another printing because we’d raved about it too much. Whether you’re a writer, a bookstore owner, a coach, an entrepreneur, a teacher, a parent—when you find something that helps you, inspires you, or moves you…pass it on. Tell people about it. Help others find what helped you.. 

Reading will never get old. One of the things that gets me excited about my job is just how much stuff there is that gets me excited…that until recently I didn’t even know existed. I’ve been doing this a long time—reading seriously since high school, obsessed with Greek and Roman history for most of that time. And somehow, I only just discovered Augustus by John Williams? A book that feels like it was written for me—Memoirs of Hadrian is one of my all-time favorites—and I didn’t even know this existed? And it’s not like it’s some obscure old thing—it won the National Book Award! Then just last month I discovered The Last of the Wine, an incredible historical novel that reminded me of everything I loved about Pressfield’s Gates of Fire and Tides of War. That’s what I love about reading: the more you read the more you realize there is much more to read. Even if you have read a lot, there is not just an endless list of great authors and books still to get to, but new ones come out every day! Maybe that’s how you know you’ve found your thing: when there seems to be no end in sight, and that never stops exciting you.

If you’ve always wanted to do it…do it. This has happened to me more than once. When my wife and I moved to a farm, I couldn’t believe how many people said, “I’ve always wanted to do that.” Same with opening the bookstore. People hear you have a small-town bookstore and they light up—“I’ve always wanted to do that.” Casey Neistat has a great line: “The right time is right now.” If you’ve always wanted to do something, do it. Stop romanticizing it. Stop overthinking it. Try it. Do it small. Do it your way. But do it.

It’s one damn thing after another. My wife suggested opening the bookstore back in the fall of 2019. Then COVID delayed us a year. Then we didn’t feel right opening for another year. Then a freak storm and some political incompetence shut down the power grid—burst pipes, busted roof. Then a global supply chain crisis made books hard to get. There’s the day-to-day stuff too: employees get sick, the internet goes out, shipments arrive damaged, a toilet leaks, the door won’t shut properly all of a sudden. But that’s how it goes. With most things in life, it’s one damn thing after another. Expect it. Work through it. Keep going.

It’s easy to focus on what’s going wrong. In any business or project, it’s easy to fixate on what’s going wrong. As I mentioned, the little daily problems don’t seem to stop. Those things demand your attention, of course. But I’ve found it helpful—even necessary—to make an effort to notice and appreciate the things that are going well, the things that are working, the little wins we get every day.

Don’t overlook simple solutions. There’s a tendency—especially when you care a lot about something—to overthink it. To assume everything has to be big, polished, expensive, professional. But great ideas can be cheap and easy too. One of my favorite bookstores in the world, Gertrude & Alice in Bondi Beach, puts sticky notes inside their books. Just little handwritten notes from employees about why they liked this or that book. No fancy plaques. No expensive signage. We started doing it at The Painted Porch too. It’s fun, it’s human, and customers love it.

Be deliberate with your space. In the book Strip Tees by Kate Flannery (a great guest when she came on the Daily Stoic Podcast—listen to the episode here), there’s a story about Dov Charney walking through an American Apparel store. He stopped, pointed to the tile beneath his feet, and said, “Do you know how much rent I pay for this tile every day? Do you know how many T-shirts we have to sell just to cover the cost of this one tile?” I didn’t witness this one—but I saw many performances like that—and now that I own my own shop, the point stuck with me: every inch of space you control is costing you something. Are you using it well? Is it serving the purpose you think it is? In a bookstore—or any business—it pays to be deliberate about what goes where. What are you putting in your most valuable real estate?

Does it make you better or worse? In the middle of the project, when the whole thing seemed impossible and doomed to fail—as we tried to open a bookstore, raise two kids when schools were closed, and make sense of the world—I wrote a note to myself: “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.

A sense of urgency matters. A couple of weeks ago, a shipment of books came in on a Friday afternoon. I heard someone on the staff say, “We’ll unpack those tomorrow.” I’m glad I heard it because I had to stop them and explain that, unless the books in those boxes were opened and the orders waiting on them were fulfilled (in time for the morning mail pickup on Saturday), they would not even begin traveling in the customer’s direction until Monday afternoon. So what seemed like a little delay until the next morning was really like a 72-hour delay. Every small delay or shortcut has second-, third-, and fourth-order consequences. That’s why it’s important—whether you’re packing boxes, replying to emails, or making big strategic calls—to think a step or two ahead. Don’t procrastinate. Do it now. Do it with urgency.

Ask why it’s being done that way. One day I noticed our team was packing shipments in a pretty inefficient way. I asked why. The answer? That’s how so-and-so showed me when I started. No one had questioned it since. This happens all the time—in businesses, on teams, in life. People inherit a process, follow it out of habit, and never stop to ask: Is this the best way? Does this still make sense? The most useful question in any system is often the simplest: Why are we doing it like this?

Know the history of your space. I was talking to Jeni Britton Bauer—the founder of Jeni’s Ice Cream—and she told me the first ice cream shops date back to the late 1600s or early 1700s. Her point was that what feels trendy or modern is often something old coming back around. That applies to bookstores, too. Or really any craft or creative business. What you’re doing might feel new or niche, but it probably has deeper roots than you think.

Learn from the cats. When we were thinking about opening a bookstore, I bought a course from a bookstore consultant. I talked to friends. I talked to bookstore owners while on a book tour. I got a lot of advice, gathered best practices, and learned what worked for others. And yet, the single most popular thing about The Painted Porch is something that never came up…the cats. In 2021, we took a family road trip to Cerro Gordo, the ghost town Brent Underwood has been restoring—my kids are obsessed with his YouTube videos—and came home with two cats who have lived at the bookstore ever since. They’re literally the most popular thing about the store. As one Yelp reviewer put it: “Nice collection of books, clean, very comfy atmosphere, but I’m not going to lie to the great people of Bastrop…I come for the cats.” Lol. So yes, do your research. Yes, learn from others. But keep in mind, some of the best parts of any project are things you can’t possibly predetermine.

Do things only you can do. Something that’s happened with Daily Stoic over the years is as it has grown, so has the number of copycats. And so we’re constantly asking, what can only we do? With the bookstore, for example, we’re lucky to have authors constantly passing through to record the podcast. While they’re here, they sign books. Sometimes we do live events with them. Those books, those experiences—you can’t get them anywhere else. This has always been good advice, but with these AI tools making it easier and easier to copy and replicate and reproduce, it’s more important than ever to find and focus on the things only you can do.

Zoom out. When we were doing a small construction project at the bookstore recently, we moved an old antique bar and found some paint on the wall, covered in plaster. Carefully scraping it away, we found a date and a kind of sign: January 16, 1922. What was happening in the world that day? Who were the people who stood there and supervised it being painted? What kind of business was in this space a hundred years ago? How many others have come and gone since? It was a humbling reminder: we’re not the first people to try something in this building, and we won’t be the last. It can be very easy on a project to get caught up in the immediacy of what’s in front of you, to get caught up in the day-to-day of running a business or chasing a goal. But every project, every place, every person is part of something much bigger—something that started long before us and will continue long after.

There’s always problems you aren’t even aware of. What started as a small construction project at the bookstore recently led to uncovering another issue, which led us to another thing that needed fixing…and that led to something else entirely. We’re lucky we tackled the initial project. One thing that keeps you up at night is all the things you don’t know are happening. The controversial Samuel Zemurray’s line—per Rich Cohen’s amazing book The Fish That Ate the Whale—was “Never trust the report.” He went to South America or Boston or wherever the business was being done and saw the situation up close for himself. He wanted first hand knowledge so as a leader he could make the right decisions. 

I will leave you with one final bonus piece of advice: hard things are good for you. It is only from doing hard things, as the Stoics said, that we learn what we’re capable of. Seneca would say that he actually pitied people who have never experienced challenges. “You have passed through life without an opponent,” he said. “No one can ever know what you are capable of, not even you.”

Opening a bookstore during a global pandemic has been the hardest thing I’ve ever done. It’s been challenging. Expensive. At times overwhelming. There were setbacks we didn’t anticipate, problems we didn’t know existed, and moments where it would’ve been easier to walk away.

Which is what’s made it one of the most interesting, meaningful, and rewarding experiences of my life. We’ve learned so much—about business, about books, about what we are capable of. We’ve built something that matters to our community and to us. And in the end, those are the things that stay with you—not the easy wins, not the shortcuts, not the stuff or the money.

So if you’re thinking of doing something difficult, if you feel called to do something big…do it. Regardless of whether it succeeds or fails, you’ll be better for it. No one will wonder what you were capable of. Not even you.

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April 2, 2025by Ryan Holiday
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This Is Something I Am Forever Grateful For

I would never say I am glad it happened.

I don’t want to dismiss the tragedy and the disruption and the loss.

But as I think about what happened five years ago, as I think about my life shutting down for the pandemic in March and April of 2020, I feel an overwhelming sense of gratitude. I see how it changed me. I see what it taught me. I see the trajectory it put me on.

I’m not talking here about the resurgence of Stoicism that came from these last few troubled years, although that too has been fascinating, exhilarating and obviously good for ‘business’ as an author. I am mostly just talking about how deeply those strange, quiet months—when I was forced to slow down and stay put—recalibrated what I value, what I prioritize, what I want my life to look like.

In March of 2020, as social distancing and lockdowns started, my wife and two young sons settled into our ranch on the outskirts of Austin. We’d lived there for five years, but we were able to live there in a way we’d never lived there before. No more commutes. No more daily trips to the store. No more weekly trips to the airport. No more waking up in hotel rooms. No more time apart.

We would spend literally hundreds and hundreds of days together…in a row. In a way that I don’t think I had ever spent in one place or with anyone in all my life (my parents having been rather busy people themselves). And never before so free from the mental load—the relentless cycle of logistics, scheduling, planning, packing, and worrying about where I needed to be next—that had always kept some part of me from being fully present.

There is no such thing as parental leave in my line of work. And, like a lot of driven people who work for themselves, I’m not sure if I could have taken time off, that I would have let myself. Instead, I’ve worked constantly for much of my career and much of my young children’s lives, accepting and chasing opportunities—even though that meant many nights in hotel rooms and on airport benches. This, in addition to those ordinary work-from-home days that all writers know, where you are technically home but are, in fact, very far away.

Suddenly, every single day, rain or shine, I was able to take my boys for a long walk in the morning. Most days, we also did their nap in the running stroller or a bike trailer. In the evening, we walked again. We got in the pool together almost every day. We read books. We ate every meal together. I never missed a bathtime or a bedtime.

How many miles did we walk on our dirt roads? How much time did we spend in the woods? How many sunrises and sunsets? How many blackberries did we pick? How many fish did we catch?

Again, I understand that this was privileged—many people had it quite badly, and I’m not just referring to the immuno-compromised. My sister spent the pandemic in a small apartment in Brooklyn. My grandmother spent it in a nursing home. We had friends who were doctors and paramedics, soldiers who were deployed. Plenty of other people still had to work in warehouses, in places and conditions they should have had to…while others lost their livelihood entirely.

So I get that it was privileged. That’s my whole point, I am saying I was incredibly lucky.

I was lucky that I got to see my own home in a new way. One thing that struck us was how beautiful that first spring was—and how new it was. Like, we’d never once, in five years, spent enough days in a row at home that we could actually track spring happening, watching the bare trees go from buds to leaves to a cool, lush forest. We’d missed blackberry season most years. We’d get home after golden hour most days. But now we noticed everything—the small, daily transformations, the subtle shifts of light through the windows, the sounds of birds we’d previously been too busy to even see.

In Chloe Dalton’s lovely new book ​Raising Hare​, Dalton—an ambitious and connected political advisor—finds herself in an old house in the English countryside. On a walk one day she comes across a leveret (a baby wild hare) and nurses it back to life. What ensues is a surreal and moving friendship, as the hare becomes a free-range companion, hopping around the house, snoozing quietly by Dalton’s side as she wrote, running in from the fields when called, drumming softly on her duvet to get her attention, even giving birth and raising babies inside Dalton’s home.

These were not particularly well-known or well-understood animals, in fact, they’re largely ignored. So she had to read not just research papers, but poetry and ancient authors just to find out what they’re supposed to eat. Spending hundreds of lonely, quiet hours with the leveret–which she never named–she learned to understand its habits and needs, seeing the world from its umwelt (to use one of my favorite words) in addition to her own. And she came to see the home and countryside that she lived in differently, too.

“I felt a new spirit of attentiveness to nature,” she writes, “no less wonderful for being entirely unoriginal, for as old as it is as a human experience, it was new to me. For many years, the seasons had largely passed by, my perceptions of the steady cycle of nature disrupted by travel and urban life. I had observed nature in broad brushstrokes, in primary colors, at a surface level. I had been most interested in whether it was dry enough to walk, or warm enough to eat outside with friends. I could identify only a handful of birds and trees by name. I hadn’t observed the buds unfurling, the seasonal passage of birds, the unshakeable rituals and rhythms of life in a single field or wood. I now marveled at the purple tinge on the black feathers of a house martin—the smallest creature I had ever seen—which flew into the house one morning…observing the gleam of the sun on the mirror finish of its plumage, before releasing it into the air.”

It’s funny. I spent 2018 and 2019 working on my book ​Stillness is the Key​. One of the main characters of the book is Churchill, whose own relationship with time and the natural world was changed by his love of painting, which he discovered in the midst of a nervous breakdown after WWI. He was introduced to it by his sister-in-law, who, sensing that Churchill was a steaming kettle of stress, handed him a small kit of paints and brushes her young children liked to play with. In a little book titled ​Painting as a Pastime​, Churchill spoke eloquently of the way painting, like all good hobbies, taught the practitioner to be present. “This heightened sense of observation of Nature,” he wrote, “is one of the chief delights that have come to me through trying to paint.” He had lived for forty years on planet Earth consumed by his work and his ambition, but through painting, his perspective and perception grew much sharper. Forced to slow down to set up his easel, to mix his paints, to wait for them to dry, he saw things he would have previously blown right past.

I was just finishing a very busy book tour for ​Stillness​ when the pandemic hit (I actually crossed through the Venice airport in late January on the day when those two Chinese tourists arrived from Wuhan—later identified as among the earliest COVID cases). I thought I knew what stillness was, but the world was about to teach me about real stillness.

For many of us, the pandemic brought everything to ​a screeching, unprecedented stop. I​t stripped everything down, broke it all apart and made so much of our normal lives–work and personal–unsafe, if not impossible. I wasn’t having to get to this plane. I wasn’t having to battle traffic to get somewhere on time. I wasn’t having to prepare for this talk or that one. There were no meetings, no dinners out, no get-togethers, no pressing deadlines.

For all it took from us, it gave us “the privilege of an experience out of the ordinary,” ​as Dalton beautifully put it​.

And yet, what did most of us do with this experience? We complained about it. We resented it. We focused on what was missing. We agitated for things to ‘go back to normal.’ As if the way things were before was how they were supposed to be!

Because of some health issues in our household, because we had the physical space, since I had some financial comfort, and because my in-person work was certainly not essential–I did not want to be responsible for getting people together and getting them sick–we continued our social distancing in a more sustainable way longer than most. I turned down work travel. I declined most social obligations. We let our employees keep working remotely.

This was one of the best decisions I ever made. I really grew as a parent–as an equal parent. I got in a lot of reading and writing and running. And as I said, I grew to really love where we live.

As Dalton writes in her book, she had the same experience.

How glad I am now that I did not leave for the city the moment it became possible. I am grateful for every additional day that I gazed out of the window. If I had gone, I would not have seen the leverets born. I would not have built the relationships I formed around the hare, with other people and with this patch of land, and felt this unexpected, uncomplicated joy, and learned not to tamp down the emotions it generates in me. I would not have looked at my life from a different perspective, and considered both what more I might be and the things I might not need. Whereas before I sought out exceptional experiences and set myself against the crowd, I take comfort in the fact that this process of self-discovery has been felt by millions before me.

Me?

I’m grateful for something like 500 consecutive bedtimes with my boys.

I’m grateful for ​the road trips we took​. I’m grateful for the projects we worked on together as a family (​designing the bookstore​, ​writing The Boy Who Would Be King​ and​ The Girl Who Would Be Free​). I’m grateful for the things it forced me to notice and work on in my marriage.

I’m grateful that it forced me to confront the reality that there are many things I don’t have to do. If you’d asked me in January 2020 if I could survive—professionally and personally—with no travel, no events, no dinners out, no get-togethers, I’d have said absolutely not. As it turned out, it was ​not only rewarding but immensely productive in every sense​. Why? Because clearly, those things I thought I had to do, I didn’t actually have to do. As it turns out, I’m better and happier when I don’t.

I’m grateful for what it taught me about human nature, about history, about adversity, about mortality, about our obligations to each other. I’m grateful that it didn’t radicalize me or turn me into an unfeeling, cruel person (what Marcus Aurelius would refer to during the Antonine Plague as the real pestilence). I’m grateful that it showed me what I needed to be most grateful for–my health, my family, the present moment. I’m grateful that it taught me how easy it can be to take so many things about our lives for granted that other people do not share and would count themselves incredibly lucky to have.

I’m grateful for what was, I think you can say, the most radical lifestyle experiment in human history. In a note to myself in the early days 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?

In the process, the difficult, painful pandemic became what POW survivor, ​Admiral James Stockdale, would describe​ as a “defining event of my life, which, in retrospect, I would not trade.”

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March 26, 2025by Ryan Holiday
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