Category: Personal Development

I had the most magical experience a few weeks ago. It wasn’t exactly time travel, but it felt like something close. I was sitting down to work on a chapter for my next book (btw, ​the third book​ in the Stoic virtue series comes out in June. I’m working on the fourth now). I had decided to write a chapter on the importance of keeping what’s called a ​commonplace book​. I sat down at my desk, pulled out my notecards, and found an old, worn notecard mentioning something that Joan Didion had written about notecards from a chapter in her book ​Slouching Towards Bethlehem​. I walked over to the shelf and pulled it down and of course, there it was, a beautiful essay in that book called “On Keeping a Notebook”, written in 1966. I got goosebumps, not just because it was exactly what I needed, but because I happened to be sitting, at that very moment, in Joan Didion’s chair (​I bought it at a charity auction​ after her death). How did I know, nine years ago when I read ​Slouching Towards Bethlehem​, when I took the time to jot that little reference, that it might be of use to future-me? “Why did I write it down?” Didion herself asks in that essay. “In order to remember, of course, but exactly what was it I wanted to remember?” I don’t know, you never really do, but the process of finding, years later, the perfect thing that I had recorded in the margins of a book or a notebook, has happened to me so many times now that I’ve begun to question the time-space continuum. When I was writing ​Courage is Calling​, for instance, I decided I would write about the Spartans at Thermopylae. I went to my shelf again and found there, in my ​Penguin Classics edition​ on page 477, what was effectively a highlighted outline of everything I needed to write this section…which had sat there silently for nearly twenty years. I didn’t even think I would be a writer when I read that book! I was just reading something that I thought was interesting! This happens time and time again. One of my favorite books to re-read is F. Scott Fitzgerald’s ​The Great Gatsby​. I love ​Gatsby​ not just because it’s an incredible book, one of the great works of the English language. I love it because it was one of the first books I ever loved. I was assigned to read and write an essay on ​Gatsby​ in my sophomore English class and I still have that copy. So when I re-read ​Gatsby​, I’m not just talking to Nick Carroway and Jay Gatsby and Meyer Wolfsheim and Scott Fitzgerald himself, I am also talking to 16-year-old me. I can see the food I spilled while I read it at the kitchen table of my parent’s house. I can see my teenage handwriting in the margins. I can also see the things I noted when I re-read it in college. I can see the notes I took when I read it in my twenties. I can see how I barely noticed the passages on page 73 the first few times I read it and I can see myself flipping back through the book to find them in 2016 when it suddenly hit me that the scene with Meyer Wolfsheim–a stand-in for the gangster Arnold Rothstein, fixer of the 1919 World Series–would be perfect for the opening of the book I was writing about Peter Thiel’s secret lawsuit, the book that would become ​Conspiracy​. Even as I write this paragraph right now, I have ​Gatsby​ on my desk to revisit some of my favorite pages. I’m struck again by those first few sentences that I’ve read dozens of times: “In my younger and more vulnerable years my father gave me some advice that I’ve been turning over in my mind ever since. Wherever you feel like criticizing anyone, he told me, just remember that all people in this world haven’t had the advantages you’ve had.” Those words have different meaning to me today than they did five years ago, let alone when I first read them at 15. Now I have kids, now I have a better sense of my own advantages in life, now I know how hard it is to write something that good without sounding preachy or lame. The poet Heraclitus talked about how we never step into the same river twice. By that he meant that the river is always changing, glowing evermore towards the sea, and we ourselves are changing, growing, getting older. The pages of a book don’t change, but we change, the world changes around them–we’re able to see and perceive things differently. That’s one of the things that Didion notes in her essay on notebooks. Notebooks, she said, are a way “to keep on nodding terms with the people we used to be.” They are blasts from the past, reminders of how easily “we forget all too soon the things we thought we could never forget.” I’ve talked before about my notecard system–which I learned from Robert Greene–so I won’t bore you with it here (​here’s a video about it​). But the reason I try to be an intentional reader, why I try to take notes and record and store what I read, is because I have seen the magic that comes from it, personally and professionally. The best time to have started a notebook or a commonplace book would have been many years ago, but the second best time would be now. Start small–record what strikes you, quotes that motivate you, stories that inspire you. Don’t think too hard, just follow your curiosity. When you read a book, write in it, fold the pages, really engage with the material. Preserve this moment in time. Capture what you’re thinking and feeling. Your future self will thank you. “It all comes back,” Didion writes at the close of her essay. […]

Several years ago I was swimming in a pool in Austin—I wish I could say it was Barton Springs, one of the wonders of the world or even the Los Angeles Athletic Club (photographed above), but it was actually a 24 Hour Fitness off I-35—and a reader recognized me as I was getting out of the water. I’m reading your book ​Ego is the Enemy​, they said. That’s funny, I replied, because I wrote it in this pool. They gave me a weird look, but I think most writers would know exactly what I was talking about. Having a physical practice is essential to the creative life. Not just because it gets you up and out of a chair. Not just because it’s good to stay in shape. But because when the body is in motion, the mind can really get to work. My routine then—it’s a little different now that I have kids, as I’ve ​written​ and ​talked​ about—was to write in the morning until I hit a point of diminishing returns. Then I’d either go for a swim, or put on my running shoes and go for a run. Depending on what time it was or whether I was writing from my home or my office, I ran one of a few go-to routes. The purple, red and gray trails in the eerie elephant graveyard of the burned-out forest of Bastrop State Park. The seven or ten mile loops along Lady Bird Lake in Austin. Or, if it’s already started to get dark, up 11th to do laps around the lit up Texas State Capitol and then down Congress to Cesar Chavez and back. Lately, I’ve been doing my runs in the morning. I’ve been biking more than I did before ​because of the ankle injury​. I’ve been doing more weight training, too. I try every day to keep my practice because, as the Jews say of the Sabbath, it keeps me. Regardless of what time, where, how far or for how long, going on a run or a ride or a swim almost always goes well. With writing, it’s the opposite. Professional writers quickly learn one reality of the job: you have more bad days than good days. It’s the rare day that the writer finds that the words come out exactly the way they were in their head. More often, one is disappointed, distracted, struggling, committed but unproductive. Therefore, the writer needs a physical practice, something that reliably goes well and gives one a sense of accomplishment, to counterbalance the mercurial muses of the creative professional. “The twin activities of running and writing,” prolific author Joyce Carol Oates writes in her ​ode to running​, “keep the writer reasonably sane and with the hope, however illusory and temporary, of control.” It can hurt sometimes, but even when it does, you feel good after. A physical practice doesn’t have to be running. “If an action tires your body and puts your heart at ease,” Xunxi said, “do it.” As I said, I like to swim. I like riding my bike. I do weights sometimes. But for you, maybe it’s jujitsu. Maybe it’s yoga. Maybe it’s stand up paddle boarding. But it’s got to be something. In one of his little books, ​Painting as a Pastime​, Churchill talks about how he discovered painting after a nervous breakdown following the Great War. This little pastime changed his life, got him outside, got him to slow down. “The cultivation of a hobby and new forms of interest is therefore a policy of first importance to a public man,” he explains. “To be really happy and really safe, one ought to have at least two or three hobbies, and they must all be real.” Hobbies are great, but I do think there is something insufficient about scrapbooking. Photography is cool. So is baking and fantasy football. But in addition to his more cerebral hobbies, Churchill would have also benefited from golf or cycling or tennis, as his famously rotund figure indicates. (He liked to dabble in bricklaying, which I guess counts, but it’s hard to recommend). At least his painting got him outdoors. He probably had to hike for a few of those landscapes he captured. Still, there is something about cardio–or any form of strenuous exercise–that’s just magic. One of Churchill’s predecessors knew this well. In ​Stillness is the Key​, I tell the story of William Gladstone, the four-time prime minister of England, who loved to chop down trees on his estate. For hours on end, to escape the stresses of high office, he would head to the forest with an axe in hand. He once spent two full days working on an elm tree with a girth of some sixteen feet. The process consumed him, leaving him no time to think of anything but where the next stroke of his axe would fall. This arboreal activity was a way to rest a mind that was often wearied by politics and the stresses of life, a challenge for which effort was always rewarded and with which his opponents could not interfere. Without the lessons he learned in those woods—about persistence, about patience, about the importance of momentum and gravity—could he have fought the long and good fight for the causes he believed in? (And to be clear, he would use the wood from these trees and actually his sons sometimes sold chips from them to raise money for charity). “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 after I stopped writing and went for a run or swim. I even had the idea for […]

Preparation is important. Planning is important. Reflection is important. I mean, I wrote a whole book called, Stillness is the Key, because it’s true. And I was just saying earlier this month that I needed to slow down and take better care of myself because I was pushing too hard. And I just read and loved Cal Newport’s new book Slow Productivity (we had a great conversation on The Daily Stoic podcast, listen here). At the same time, I also just hung up two signs at The Daily Stoic offices and in the backstock of The Painted Porch that say “A Sense of Urgency.” It’s something I cribbed from the kitchens of Thomas Keller, the creator of Per Se. He wanted his staff to understand that they weren’t waiting on customers…the customers were quite literally waiting for them. Sure, making great food takes time and it can’t be rushed…but it also can’t be slow-walked. I’m a ‘sense of urgency’ guy. I always have been. As I was working on a draft of this article, one of my former employees sent me a short piece about the concept of “clock speed,” which in the world of computing refers to how quickly something can execute instructions. “Something you are very good at,” this former employee (and now friend) wrote. “You keep the tempo/momentum very high and if there is ever a bottleneck somewhere (decision or input), you process that as soon as physically possible. You return the ball very quickly.” It’s funny that he said “return the ball” because that’s something I used to say a lot. I’d say look, we don’t control how long other people take to do things, but we do control how long we take. We want to hit the ball back into their court—I’d rather be waiting for them than them be waiting for us. I started using a different metaphor more recently. 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. Meaning, I’m not pleased if I hear it took 2 weeks to make the decision about how many to order, or that somebody was slow in processing an invoice. I don’t control how long it takes to make stuff, but I do control when the clock starts on it. 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). It struck me that this has become a kind of dividing line between success and failure within my team. Those who haven’t worked out haven’t been able to start the clock or return the ball very quickly. It’s not just my team—it’s a source of frustration that fills the letters and dispatches of just about every great general, admiral, and leader throughout history. In the American Civil War, General George McClellan, for instance, seemed utterly incapable of getting to the fight quickly, to the complete exasperation of everyone who worked with him. There’s even a story about Lincoln coming to meet with McClellan for a meeting but McClellan blew him off because he wanted to go to bed (he thought it could wait until the next day). Only after repeated prods from Lincoln—by “sharp sticks,” one of his secretaries said—did McClellan finally begin to move against Lee in 1862, taking nine days to cross the Potomac. “He’s got the slows,” Lincoln said in frustration. Joking to his wife after visiting the general in the field, Lincoln poked fun at his parked commander. “We are about to be photographed [if] we can sit still long enough,” he said. “I feel General M. should have no problem.” McClellan was a brilliant soldier. But groaning under the weight of his baggage train, his conservatism, his entitlements, his paranoia, and his precaution, he was constitutionally unable to do things quickly, to act urgently, to care about the people waiting on him. He seemed to not understand how much the country was waiting on him, how much it was depending on him sending the message that the North was in the war to win it. Deep down, maybe he didn’t actually want to win the war–at least not early–hoping that a negotiated end might preserve slavery. Lincoln’s big mistake, honestly, was not firing him sooner. You could say Lincoln had the slows himself there–or was in denial–about what needed to be done. Replacing McClellan was not easy and he had to cycle through a number of replacements, but if Lincoln had started the clock sooner, who knows how much sooner the war would have ended. Not that I’m not saying you need to rush everything, I’m really not. There’s another Civil War general I like, General George Thomas. Thomas was hardly known for his speed. His nickname, in fact, was “Old Slow Trot,” which he had earned for the discipline he enforced as a cavalry commander. But it really wasn’t that he was slow; he was deliberate. After all, a trot is not a walk. Some people thought he was too slow and maybe sometimes he was. Thomas found himself at odds with Grant for not moving fast enough against General Hood’s army at Nashville, taking such an exasperatingly long time to get moving on Grant’s order to “attack at once” that Grant moved to personally relieve him. Grant thought that Thomas wasn’t hurrying, that he was dragging his feet. In fact, he was fully committed–unlike McClellan–to attacking, he just wanted to ensure he succeeded when he did so. Having prepared properly, supplied adequately, and trained effectively, he waited for the right moment and then attacked with all deliberate speed. Thomas annihilated his enemy in the Battle of Nashville in December 1864, […]

Spring is my favorite time of year in Texas. After a dreary winter, the colors come back. The birds are out. The days last longer. The breeze is light. The air is cool. The leaves come back on the trees around my ranch. Suddenly, the woods are full and dense. The grass comes in. The bluebonnets flood the fields. Soon enough, blackberries will be ripe for the picking. But as beautiful as it all is, there lurks beneath a kind of darkness. Phillip Larkin’s bittersweet poem captures this darkness well: The trees are coming into leaf Like something almost being said; The recent buds relax and spread, Their greenness is a kind of grief The inherent grief is the passage of time. Each season brings new life, yes, but also marks the cessation of life. It’s a painful truth, the poem points out, written in the rings of the tree. Winter is dead and over…and all of us a little more so, too. Think back to those cold winter afternoons where you didn’t want to go outside. Where you didn’t want to do anything at all. **Where you said to yourself, I can’t wait for this to be over. You weren’t killing time…that was time killing you. I promise you though, I’m not just looking at natural beauty and finding the morbidity in it. When I look out over my ranch in the spring, I also think of the last stanza of Larkin’s poem, which is actually quite hopeful. Yet still the unresting castles thresh In fullgrown thickness every May. Last year is dead, they seem to say, Begin afresh, afresh, afresh. Seneca would’ve liked those last two lines. Not only did he also point out that death isn’t this thing that happens once in the future, but is happening always, with every second passing; he said that the one thing all fools have in common is that they’re always getting ready to start. They know that they should begin afresh…they just don’t. It’s easy to look at the budding flowers, the sprouting plants, the longer days and warmer weather and take the change and growth for granted, to live vicariously through it. But we can’t stop there. We have to match their energy and change with them. We can’t wish another season away or simply wait it out. In fact, we shouldn’t let a single day go by that way. The Stoics would say that each morning is a new season. Every moment is an opportunity to start life anew, to choose a new way, to rededicate yourself to your philosophy. “Begin at once to live,” Seneca said, “and count each day as a separate life.” “Think of yourself as dead,” Marcus Aurelius wrote. “Now take what’s left of your life and live it properly.” If you’re looking to leap into something better this March, we just put together ​The Daily Stoic Spring Forward Challenge​. In the spirit of beginning afresh and of growth and renewal, this 10-day challenge is designed to bring a sense of clarity and purpose to your life. Each day, you’ll be presented with a challenge to help you: Simplify your life Gain control over your time Face your fears Expand your point of views Abandon harmful habits Do more with your days Here’s what you’ll get: 10 custom challenges delivered daily (15,000 words of all new original content) 10 custom video messages where I’ll guide you through each day A printable 10-day calendar with custom illustrations to track your progress Access to a private community to communicate and motivate other participants A wrap-up live Q&A with me and thousands of other Stoics It was Marcus Aurelius who said: “This is what you deserve. You could be good today. But instead you choose tomorrow.” Don’t choose tomorrow. ​Choose to be good today​ and challenge yourself to demand more for your life this season. If you’re ready for the challenge, ​I hope you’ll join me​. Just head to ​dailystoic.com/spring​ to sign up today! Tweet

A few weeks ago, I was running early in the morning in Arizona. I probably should have waited for it to get light out, but I had a busy day ahead of me and wanted to squeeze it in. I even remember thinking as I left, as I turned on my woefully insufficient flashlight on my phone, I hope this isn’t a mistake. The answer came not three steps later, when I went down and my ankle rolled hard to the left. After washing off my scrapes and testing the ankle, I decided to push through the run and got a good five miles in. Tough, right? Just hours later, I could barely keep my shoe on, and putting even the slightest weight on it was painful. By that night, a long bruise covered the length of my foot. I took about ten days off from running–dutifully elevating and icing it when I could—and even those ten days felt like an eternity to me. Going nearly out of my mind and having tested it with a few brisk walks, I biked and then started running again. My wife told me I was crazy but I was starting a new book and I needed the activity to balance me out. I couldn’t afford not to, I said. All was well until a Friday morning about two weeks later. I was giving a talk in Kentucky later that evening and wanted to run before we headed to the airport. I didn’t even make it down the stairs of my back porch. My ankle, still weaker than I thought, rolled hard to the left as I came down the last stair. It was nothing like the last time. The pain was excruciating. I heard an audible pop, and from the signals my leg was sending to my brain, I honestly expected to look down and see bone sticking out of my skin. Sounds came out of my mouth that I had no control over and when I laid down—unable to put any weight on my leg—my body started to shake. I was hurt, but mostly, I was mad at myself. I knew in that instance I was about to get an abject lesson in what the writer John Steinbeck called “indiscipline of overwork.” Pushing yourself past your limits, using brute force, he said, was “the falsest of economies.” I had pushed myself too far generally and then ignored my recovery. Now I was going to pay. At the orthopedist shortly thereafter, I got good news—not broken—and bad news—a severe sprain with some ligament tearing. No surgery required, but it would need some serious physical therapy. A month, ideally, six weeks of recovery, he told me. And no running for six weeks. That’s what returning early would cost me. This is a lesson I have learned and not learned before. In fact, I open ​Ego is the Enemy​ with a recounting of my own workaholism. I use that Steinbeck quote in ​Discipline is Destiny​, where I talk about the importance of what they called load management in the NBA. I have a whole chapter about it in ​Stillness is the Key​. I tell the story of Prince Albert, a hard worker from the day he married into the British royal family. Indeed, many of the so-called Victorian traits of the era originated with him. He was disciplined, fastidious, ambitious, conservative. Their schedule was packed with meetings and social events, as Albert tirelessly worked, even to the point of occasional stress-induced vomiting. He would write to his stepmother, “I am more dead than alive from overwork.” Still, he soldiered on for years, working harder and harder, forcing his body to comply. And then suddenly, in 1861, it quit on him. His strength failed. He drifted into incoherency. At 10:50 p.m. on December 14, Albert took his three final breaths and died. The cause? Crohn’s disease, exacerbated by extreme stress. He had literally worked his guts out. To give you another personal example, I wear an Apple Watch, and I have this goal: I try to burn a thousand active calories every single day. A few years ago, I got into a rhythm for many consecutive days, and if you have an Apple Watch, you know you start getting these alerts and badges to nudge you into keeping it going. Even though this is all utterly meaningless—it’s not even public—it got harder for me to stop each day. Doing the exercise was nothing to me, but not hitting the benchmark? That was what I was dreading. I finally did stop after way too many days without recovery, I think because I had a long international flight. You know what the reward for my ‘accomplishment’ was? I came down with mono! I was talking to my friend Brad Feld (who is a great startup investor and has suffered from burnout and overwork himself) shortly after. I was joking to him, “Can you believe I got mono? Isn’t this what girls get from making out with the football team in high school?” And he said, “No, it’s actually very serious.” He said, “Mono = Ryan_wore_himself_out.” I’d worn myself out so much that I got mono, which took me two months to recover from. Talk about the falsest of economies–skipping a day or two of rest here and there cost me months. I wore my immune system down. I worked too hard for too long, and it ended up being a problem for me. I couldn’t write. I couldn’t think. My mind was all messed up, and it was really hard. In Japan they have a word, karōshi, which translates to death from overwork. In Korean it’s gwarosa. Is that what you want to be? A workhorse that draws its load until it collapses and dies, still shod and in the harness? Is that what you were put on this planet for? Do you want to be the artist who loses their joy for the process, who has […]

From my first desk job working at my college newspaper. My first job was working at a small deli and grocery store in Lake Tahoe when I was 15. It was a job that came full circle some twenty years later when my wife and I bought a place called ​Tracy’s Drive-In Grocery​ in 2021, a little place that’s been in business since 1940. I’ve had my fair share of gigs in between. I worked in fast food. I was the director of marketing for a publicly traded company. I’ve been a lifeguard. I dropped out of college to be a research assistant to an author. I worked a desk at a talent agency in Beverly Hills. I’ve started multiple businesses. I’ve freelanced. I’ve been lucky enough to speak and consult with multi-billion dollar companies and Super Bowl winning sports franchises, family offices and law firms. I wouldn’t say I’ve done it all because that’s one thing you learn–how much you have left to learn–but I have done a lot. I’ve had to think a lot about how to be a good employee as well as how to be a good boss. I’ve seen what makes good companies succeed and bad companies fail. I’ve seen how people get ahead…and how people get stuff. I’ve also written a lot about this over the years, as I was figuring it out. In fact, many times I had to talk to bosses about this “little thing I do on the side” which was writing until eventually, the business stuff itself because of the stuff I do on the side. And now I have to have the conversation the other way with the people who work for me at ​Daily Stoic​ or ​Brass Check​ or at ​The Painted Porch​ or at ​Tracy’s​: Ok, but what do you really want to do and how can I help you get there? Anyway, this post is about that. The best of those lessons—things I wish I’d been told when I was just starting and things I still tell myself. Some of them might be exactly what you need to hear right now. Some might not apply to you yet, or ever. That’s okay. Whether you’re just starting out, looking to make a big change, or aiming to reach new heights in your current role, I hope you’ll find something here that helps you navigate your own unique path. Be quiet, work hard, and stay healthy. It’s not ambition or skill that is going to set you apart but sanity. I remember once 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.” I thought of that conversation when I saw that famous scene in Mad Men where Peggy complains that Don never says thank you. “That’s what the money is for!” he tells her. The thing that’s wrong about imposter syndrome is that for the most part no one is thinking about you at all. They’re too busy with their own doubts and their own work. When I was starting out as an assistant in Hollywood, someone told me that the best thing I could do was make my boss look good. Don’t worry about credit, they said. Forget credit so hard that you’re glad when other people get it instead of you. It ended up being pretty decent advice, but it was nowhere near the right wording. I think a better way to express it would be: ​Find canvases for other people to paint on​. Come up with ideas to hand over to your boss. Find people, thinkers, up and comers to introduce them to. Cross wires to create new sparks. Find what nobody else wants to do and do it. Find inefficiency and waste and redundancies. Identify leaks and patches to free up resources for new areas. Produce more than everyone else and give your ideas away. The person who clears the path ultimately controls its direction, just as the canvas shapes the painting. Very rarely have I ever let anyone go because they did not have the skills to do their job. It’s almost always their unwillingness to learn those skills or their inability to take feedback. When I was 20 years old, I was working at this talent agency in Hollywood, and I got invited to this important meeting. As they were talking about stuff, I interjected and said something. My mentor took me aside after and he said, why did you say that? Did you think it actually needed to be said or did you just feel like you wanted to have something to say? I think about that all the time. It’s in ​The 48 Laws of Power​ — Always say less than necessary. Saying less than necessary, not interjecting at every chance we get—this is actually the mark not just of a self-disciplined person, but also a very smart and wise person. The boss/mentor/biz can’t want you to succeed more than you want it. You have to be the driver of your own life/career/advancement. I was working full time at American Apparel but planning my next move, saving my money and thinking about writing a book. Over lunch one day, Robert Greene told me, Ryan, while people wait for the right moment, ​there are two types of time​: Dead time—where they are passive and biding and Alive time—where they are learning and acting and getting the most out of every second. Which will this be for you? When you’re lacking motivation, remind yourself: discipline now, freedom later. The labor will pass, and the rewards will last. When I first moved to Austin in 2013, I went out to lunch—fittingly—with a writer named Austin Kleon. I was a longtime fan of his book ​Steal Like an Artist​ (his book ​Keep Going​ is another favorite). After we ate, […]