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RyanHoliday.net - Meditations on strategy and life
Blog

You Need This Now More Than Ever

Come see me live in Austin and San Diego this year. ​Get your tickets here​.

It’s ironic that the only thing we all seem to agree on lately is that there’s a lot to be angry about.

This is what traditional media and social media both fuel…and then there is also the fact that reality itself is pretty awful.

Our airports suck. Our politicians are cowards. Our systems are broken. Things are too expensive. Our environment is being ravaged. Horrible things are being done by people who seem to revel in the pain and anguish their actions cause.

I mean, how could you not be pissed off?

As they say, if you’re not outraged, “You’re not paying attention.”

And actually, the fact that a lot of people aren’t paying attention is another thing to be mad about!

Except…this is exactly the wrong response. To injustice. To inefficiencies. To broken systems. To frustrations.

Because anger doesn’t make things better. It always makes things worse.

If anger were something that made people better, do you think athletes would work so hard to get under the skin of their opponents? Do you think lawyers would try to attack and frustrate witnesses under cross-examination? Of course not. It is precisely because anger is blinding, because it makes us irrational, that one opponent uses it to undermine another.

What we need—in sports, in life, in activism—is restraint, not rage.

Oh, but that’s very privileged of you to say, one might think. You wouldn’t be so blasé if things were worse for you personally.

History overwhelmingly disproves the idea that self-composure is a synonym for resignation. Think of Abraham Lincoln. A defining moment of his life came in 1841 when he, then no more than a successful Midwestern lawyer, saw a group of slaves chained together on a riverboat like “so many fish on a trotline.” Abolitionists had long witnessed such scenes and many became radicalized. Lincoln’s reaction was different—not anger, but a deep, profound sadness at the injustice. This was key. For all the abolitionist passion, it was Lincoln who spent the next two decades plotting political change that achieved what generations had failed to do. Unlike even the radicals, he never doubted the Union could be preserved, the war won. He steered the ship unswervingly through those terrible times, preaching understanding, forgiveness, and mutual culpability—even keeled in his determination to improve the world.

The Women’s Rights Movement—while many of the suffragettes involved had blind spots, even abhorrent views about class or race—was defined by their remarkable ability to put aside differences and come together for the cause. “For the first time in the woman movement,” Carrie Chapman Catt would say at the opening of the seventh conference of the International Woman Suffrage Alliance in Budapest in 1913, “it is expected that Hindu, Buddhist, Confucian, Mohammedan, Jewish and Christian women will sit together in a Congress uniting their voices in a common plea for the liberation of their sex from those artificial discriminations which every political and religious system has directed against them.”

The Civil Rights Movement—per Martin Luther King’s leadership as well as the leadership of brave people like John Lewis—was defined not by anger, but by love. By a call to our better angels, not our worst ones. So was Gandhi’s. New to South Africa after a couple of frustrating years struggling to establish himself as a lawyer in India, Gandhi was humiliatedat a Maritzburg train stop in 1893, thrown off a train because of his race. But it wasn’t anger that he stewed in as he sat there shivering in the cold waiting for a ride, it was something deeper, something he later referred to as the most profound spiritual experience of his life. “I began to think of my duty,” he wrote. “Should I fight for my rights or go back to India?…It would be cowardice to run back to India…The hardship to which I was subjected was superficial—only a symptom of the deep disease of color prejudice. I should try, if possible, to root out the disease.” There at that train station, in that moment of pausing to weigh his options, a floundering young lawyer made the choice that would turn him into the crusader who changed the world.

It’s not that things aren’t awful. It’s not that things aren’t outrageous. It’s not that you should simply accept the injustices and the cruelty that are happening all around you. As ​we often talk about over at Daily Stoic​, to think that this is what the Stoics would advise is to miss who they were and what they did. Cato fought valiantly, selflessly in the hopes of preserving the Roman Republic. George Washington fought valiantly, selflessly in the hopes of forming one. Epictetus and Musonius Rufus were exiled for their transgressive teachings. Thomas Wentworth Higginson, the translator of Epictetus, led black troops for the Union in the Civil War. The Stoics were involved in public life, they were involved in important causes, they lived in a scary world where outrageous things happened on a daily basis.

And it is precisely for this reason that the Stoics cultivated poise and restraint and self-command. Because the outrages and injustices of their time demanded it. Not apathy, but the ability to step back and be objective, to be strategic, to be diplomatic, to not despair or scream or alienate.

In fact, Washington’s favorite expression, borrowing from a play about Cato, draws on this idea, that we must be able to look at everything “in the calm light of mild philosophy.” It was in the calm and mild light that Washington approached the news that one of his generals was slandering him behind his back. It was in the calm and mild light that Washington dealt with the saddening realization that he and his wife could not have children. It was in the calm and mild light that Washington approached a mob-like meeting of his officers who threatened mutiny against the new American government, slowly, masterfully, talking them back from treason.

In June 1797 alone, Washington wrote this reminder in three separate letters, trying to stop himself from rushing to judgment or losing control of his emotions and instead looking at the situation with the temperament befitting the father of a country.

Washington refused to get upset, he refused to get angry—no matter the insult, no matter the injustice, no matter the betrayal. And it was precisely this self-control that allowed him to direct his efforts towards his great task—freeing a colonial people from the subjugation of a capitalistic imperial empire, to put it in modern language—so it cannot be argued that he simply tolerated the status quo.

Like the rest of us, this was not his natural disposition. He was not exempt, a friend said, from the “tumultuous passions which accompany greatness, and frequently tarnish its luster.” Fighting them was the first and longest battle of his life—and, as another friend said in his eulogy, his greatest victory: “so great the empire he had there acquired, that calmness of manner and of conduct distinguished him through life.” As Washington’s great biographer ​Ron Chernow told me on the Daily Stoic podcast​, “He wanted to see things through the calm light of mild philosophy—it was always an ideal. It was not something that was easy to achieve. And occasionally, his self-command would break down. But he imagined that he had to embody the nation and had to live up to a certain ideal of courage, temperance, wisdom, and justice. That became a description of George Washington, but again, this was something earned, something achieved, over many years.” Washington wasn’t naturally Stoic; he made himself this way. Not permanently but anew every minute, every day, in every situation, as best he could. He had the initial reactions we all do, but he tried to put every situation up for a kind of review, searching for a better light to explain and understand it.

We need this view more than ever today, especially if we hope to change things for the better. We can’t fly off the handle. We can’t say everything we think. We can’t give in to those initial feelings of disgust, rage, contempt, or resentment.

No, we must do as the Stoic Athenodorus told the emperor Augustus—something he wanted him to follow always. “Whenever you feel yourself getting angry, Caesar,” he instructed, “don’t say or do anything until you’ve repeated the twenty-four letters of the alphabet to yourself.” Or try the principle that artist Marina Abramović lays down in her book ​Walk Through Walls​. “If you get angry,” she writes, “stop breathing and hold your breath until you can’t hold it anymore, then inhale fresh air.”

We know that between every stimulus and its response, every piece of information and our decision, there is space, one with room enough to insert our philosophy. Will we use it? Use it to think, use it to examine, use it to wait for more information? Or will we give in to first impressions, to harmful instincts, and old patterns?

The pause is everything.

The one before . . .

. . . jumping to conclusions

. . . prejudging

. . . assuming the worst

. . . rushing to solve your children’s problems for them (or put them back to sleep)

. . . forcing a problem into some kind of box

. . . assigning blame

. . . taking offense

. . . turning away in fear.

It is a brief space, to be sure, but in it lie the choices that shape the course of events in our own and each other’s lives. Using that all-important space to respond isn’t easy. As I said above, this is not something that comes naturally to most of us. It’s a discipline, something one gets better at through practice and repetition. To get better at this in my own life, as a kind of tool to strengthen my own practice of using the space between stimulus and response, ​I carry this coin in my pocket​. One side reads DELAY IS THE REMEDY (a nod to Seneca’s line, “The greatest remedy for anger is delay”), which is encircled by the 24 letters of the alphabet (a reminder of Athenodorus’ advice to silently run through them before reacting in heated moments). The reverse is a polished, mirror-like surface, inspired by Seneca’s suggestion to look at oneself when gripped by anger—not only because the sight of our own unflattering reflection can be jarring enough to prevent an unflattering response, but also because “whoever comes to a mirror to change himself has already changed.” Encircling the mirror are the words Pausa et Reflecte, Latin for pause and reflect.

​Get your medallion here.​

Today, as people throughout history always have, we face—individually and collectively—problems and injustices that are complex and urgent. Which requires that we bring our best, calmest, most focused selves to them. We don’t want to hand our enemies extra ammunition. We don’t want to make things worse. We don’t want to widen divides and deepen hostility. Instead, we must meet these problems and injustices with precisely the opposite traits of those that created them in the first place. Like Lincoln, Gandhi, Washington, the leaders of the Women’s Rights and Civil Rights Movements, we must meet cruelty with compassion, hardship with courage, provocation with self-control, and injustice with the calm, mild determination to improve things.

Whether it’s a triggering post on social media or a costly mistake at work, an obvious lie someone tried to deceive us with, an insubordinate employee, a difficult obstacle, a casual insensitivity, or a complex problem—everything must be met with a measured and mellow eye.

We can’t make decisions on impulse. Again, that’s not to say we won’t have impulses. It’s that we must be disciplined enough not to act on them.

Not until we’ve paused and reflected.

Not until we’ve counted the letters of the alphabet, inhaled fresh air, and looked in the mirror.

Not until we’ve sat for a bit in the space between stimulus and response.

Not until we’ve put things under or in the calm light of mild philosophy.

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August 13, 2025by Ryan Holiday
Blog

This Is A Lesson I Hope To Pass Down

This originally ran in The Free Press.

Poems have always been earnest. That’s why some of them are so cringe. 

Rhapsodizing about nature. Pouring out your heart to a lover. Finding deep meaning in small things. Brooding on mortality.

But a few years ago, I was talking to Allie Esiri for the Daily Stoic podcast about her wonderful book A Poem For Every Night of the Year, which I have been reading to my sons since they were little. I mentioned that I was struck by the earnest desire for self-help and self-mastery in many of the 19th-century poems written by male authors. 

You might be familiar with some of them. 

Kipling’s If— is obviously a classic of this genre. So is Henley’s Invictus. Adam Lindsay Gordon’s Ye Weary Wayfarer is another one of my favorites. 

“Life is mostly froth and bubble,

Two things stand like stone,

Kindness in another’s trouble,

Courage in your own.”

It must be acknowledged that many of the most famous of these poems were products of the British Empire at the height of its imperial power. While I’m pleased that we no longer publish poems calling a generation to pick up ‘the White Man’s burden’ or celebrating the suicidal (and avoidable) charge of the Light Brigade, I would like to point out that there was once a time, not that long ago, when an average person would pick up their daily newspaper and find a totally straightforward, understandable poem full of advice on how to be a good person or navigate the difficulties of life. 

Perhaps because it doesn’t have any jingoism or machismo—just the source code for existence—one of my favorites of this genre has always been one that is uniquely American: Longfellow’s A Psalm of Life.

It opens quite powerfully, 

Tell me not, in mournful numbers,

     Life is but an empty dream!—

For the soul is dead that slumbers,

     And things are not what they seem.

 

Life is real! Life is earnest!

     And the grave is not its goal;

Dust thou art, to dust returnest,

     Was not spoken of the soul.

 

Not enjoyment, and not sorrow,

   Is our destined end or way;

But to act, that each to-morrow

   Find us farther than to-day.

I was a kid in the 90s. I was in high school in the early 2000s. I started my career in the citadel of hipsterdom, American Apparel. Everything was couched in irony. There was a self-consciousness, an almost incapacity to be serious. The drugs and the partying and the sex were, I suspect, hallmarks of a culture distracting itself with pleasure so it would not have to look inward and come up empty. 

Is that really what we’re here for, Longfellow asks? No, he says, we’re here to work on ourselves and to get better, to make progress—for tomorrow to find us a little bit further along than we are today. 

Do things! Make things! Try your best! You matter! That’s what Longfellow is saying.

A 13-year-old Richard Milhous Nixon was given a copy of A Psalm of Life, which he promptly hung up on his wall, memorized, and later presented at school. Perhaps it’s because of people like Nixon—or Napoleon or Hitler—that we shy away from talking about individuals changing the world these days. The ‘Great Man of History Theory’ is problematic. It’s dangerous. It’s exclusionary. The problem is that in tossing it, we lose the opportunity to inspire children that they can change the world for the better, too. 

Many of Longfellow’s poems do precisely this: There’s one about Florence Nightingale, an angel who reinvents nursing. There’s another about Paul Revere and his midnight ride to warn revolutionary Patriots of approaching British troops. He celebrates Native American heroes in “The Song of Hiawatha.” They are not always the most historically accurate accounts, but to borrow a metaphor from Maggie Smith’s poem, “Good Bones”—which, again, some pretentious folks might find cringe—when we read poems to our children, we are trying to “sell them the world.” Will we sell them a horrible one? Or we will sell them on all the potential, the idea that they could “make this place beautiful”?

One of the reasons I find so many modern novels boring and end up quitting most prestige television is that everybody sucks. Nobody is trying to be good. Nothing they do matters. I’ve even found that many children’s books fall into the same trap. They are either about nonsense (pizza, funny dragons, etc) or they are insufferably woke (pandering to parents instead of children). Academia has been consumed by the idea that everything is structural and intersectional and essentially impossible to change. History was made by hypocrites and racists and everything is rendered meaningless by the original sins and outright villainy of our ancestors.

To be up and doing, as Longfellow advises, laboring and waiting, they would claim, is therefore naive. His privilege is showing when he tells us to live in the present and have a heart for any fate. One Longfellow critic has referred to the poem’s “resounding exhortation” as “Victorian cheeriness at its worst.”

But what’s the alternative? Because it’s starting to feel a lot like nihilism. I’m not sure that’s the prescription for what ails young men these days. In fact, isn’t that the cause of the disease?

I draw on one of the lines from A Psalm of Life in my book Perennial Seller, about making work that lasts: “Art is long, and Time is fleeting.” There’s a famous Latin version of this expression: Ars longa, vita brevis. 

I find it depressing how ephemeral and transactional most of my peers are. They chase trends and fads. They care about the algorithm and the whims of the moment—not about making stuff that matters and endures. Longfellow urges us to resist the pull of what’s hot right now—to think bigger and more long-term, to fight harder:

In the world’s broad field of battle,

   In the bivouac of Life,

Be not like dumb, driven cattle!

  Be a hero in the strife!

That stanza is an epigraph in another one of my books, Courage is Calling. I return to it throughout the book because that’s what these things—earnestness, sincerity, the audacity to try, to aim high, to do our best—require: courage. It takes courage to care. Only the brave believe, especially when everyone else is full of doubt and indifference. As you strive to be earnest and sincere, people will laugh at you. They will try to convince you that this doesn’t matter, that it won’t make a difference. Losers have always gotten together in little groups and talked about winners. The hopeless have always mocked the hopeful.

It’s been said by many biographers—often with a sneer—that the key to understanding Theodore Roosevelt (who would have certainly seen Longfellow strolling through Cambridge while he was an undergrad at Harvard) is realizing that he grew up reading about the great figures of history and decided to be just like them. Roosevelt actually believed. In himself. In stories. In something larger than himself. It is precisely this idea that Longfellow concludes Psalm with:

Lives of great men all remind us

   We can make our lives sublime,

And, departing, leave behind us

   Footprints on the sands of time;

But this is not mere hero worship, because Longfellow qualifies it immediately with a much more reasonable, much more personal goal, explaining that these are,

“Footprints that perhaps another,

     Sailing o’er life’s solemn main,

A forlorn and shipwrecked brother,

     Seeing, shall take heart again.

 

Let us, then, be up and doing,

   With a heart for any fate;

Still achieving, still pursuing,

   Learn to labor and to wait.

Indeed, Longfellow would hear, not long after the poem’s publication, of a soldier dying in Crimea, heard repeating to himself with his final words, “footprints on the sands of time, footprints on the sands of time, footprints on the sands of time…” 

A Psalm of Life is a call to meaning. A call to action. A call to be good. A call to make things that matter. A call to try to make a difference—for yourself and others. A reassurance that we matter. That although we return to dust, our soul lives on.

That’s why I read it to my sons. That’s the lesson that I want to pass along, a footprint I am trying to leave behind for them now, so that they might draw on it in some moment of struggle far in the future. So that they can always remember why we are here:

Not enjoyment, and not sorrow,

   Is our destined end or way;

But to act, that each to-morrow

   Find us farther than to-day.

One foot in front of the other. One small act after one small action. One little thing that makes a difference, for us and for others.

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August 6, 2025by Ryan Holiday
Blog

Everything (And I Really Mean Everything) Is A Chance To Do This

Get the limited edition collector’s set of my series on The Stoic Virtues.

I think people get it wrong.

I know I did.

When the Stoics say that the obstacle is the way, that there’s an opportunity in every obstacle, most of us take that to mean there’s some way to turn adversity into advantage.

We think of entrepreneurs pivoting during a downturn and building a billion-dollar business. We think of an investor buying back their own stock or taking advantage of being underestimated by their competitors. We think of a general using the bad weather as cover. We think of an athlete coming back stronger after an injury. We think of some rejected artist going independent and building their own label.

That’s how I was thinking about obstacles and opportunities when I wrote ​The Obstacle is the Way​ in my twenties. The simplest idea at the center of the book is that there are hidden advantages in every problem, that businesses and teams and people can take seemingly impossible situations and triumph over them. “Hard times can be softened,” Seneca writes in one of his essays, “tight squeezes widened, and heavy loads made lighter for those who can apply the right pressure.”

But what I’ve come to understand in the intervening years is that the Stoics were getting at something more profound than the fact that every downside can be flipped into some kind of advantage or transformed into a success story.

They had to.

Because it would be insane (and insulting) to say that terminal cancer was an advantage. Was there a way for Marcus Aurelius to spring forward after he buried another one of his children? Seneca can say that hard times can be softened, but then again, he didn’t have to live like Epictetus, not just through slavery but with a crippling disability from the torture he underwent at the hands of his master.

What I’ve come to understand is that the “opportunity” the Stoics saw inside adversity, big and small, was the opportunity to practice virtue. That is, it was a chance for them to rise to meet an occasion, to do the right thing, to be magnificent or magnanimous, even when they were heartbroken, even when they were being kicked around by life, even when they were dying.

Ok, so what is virtue?

In the ancient world, virtue consisted of four key components:

​Courage​—bravery, fortitude, honor, sacrifice…

​Temperance​—discipline, self-control, moderation, composure, balance…

​Justice​—fairness, service, honesty, fellowship, goodness, kindness…

​Wisdom​—knowledge, education, truth, self-reflection, peace…

Marcus Aurelius called them the “touchstones of goodness”—guiding principles for how to act, who to be, and how to respond in any situation. And there really is no situation that we can’t use as a way to practice these virtues. Even the hardest, most tragic, most heartbreaking moments of life—a terminal diagnosis, a crippling injury, losing your livelihood, burying a loved one—can be transformed by endurance, by selflessness, by courage, by kindness, by decency.

When I interviewed ​Francis Ford Coppola on the Daily Stoic podcast​​, he shared how he’s been getting through a recent tragedy in his own life—losing his wife of 60 years. “There was a Marcus Aurelius quote that really lifted me,” he told me, “which was that ‘if you lose a loved one, honor her.’ In a sense, try to be more like her, and then she’ll live on in your actions. My wife was very good—if someone was alone or sick or something, she’d call them up and be comforting to them. And I’m not like that, you know? So I started to do that. People that I know—some guys my age who have no grandchildren—I call them up and say, ‘Hey, how are you?’ And they are so pleased and so kind. And that’s how I keep my wife in my life.”

Beautiful. And closer to what I think it really means when we say the obstacle is the way.

I’ve tried to apply this formula practically in my business and creative life, but also in the difficulties I’ve faced in my life. The last decade and a half has been good to me in many ways. It’s also been…a lot. There were natural disasters, floods and fires, a freeze that broke the power grid and most of our pipes. A long drought that devastated our livestock and land. A tragic, years-long pandemic that dashed countless plans (nearly killing the ​independent bookstore we opened in the teeth of it​). Disputes with business partners. An employee caught embezzling. Funerals and late-night phone calls with news you never want to get. The company where I made my bones went bankrupt, taking with it not just much of my résumé but what was supposed to be several years’ salary in stock options. There was a falling out with family. Hundreds of thousands of miles on the road. There was getting skunked on the bestseller lists, creative differences, daily battles with procrastination.

I remember in the early days of the pandemic, I wrote a note to myself along these very lines:

In spending much of that time working on the ​Stoic Virtues Series​—four books, each on one of the cardinal virtues—I have come to more fully understand what the Stoics were getting at: LIFE IS ALWAYS DEMANDING ONE OF THESE VIRTUES FROM US. Always demanding us to be a good person despite the bad things that have happened. To do good in the world despite the bad that has befallen you. And in good times—in the face of the temptations, distractions, responsibility and obligations and obstacles that come with success and abundance—to be humble, to be disciplined, to be decent, to be generous, to hold true to your values.

When I look at the world right now, as frustrated and alarmed as I am by it, what I try to remind myself is that it’s moments like this that demand virtue from us. We don’t control so much of what’s happening. We wouldn’t choose so much of this. But here it is. What are we going to do about it? Who are we going to be inside it?

The fourth and final book in the virtue series, ​Wisdom Takes Work​, is set to come out this fall (but is officially available now for preorder at ​dailystoic.com/wisdom​, where we’re doing a run of preorder bonuses like signed and numbered first editions, early access to the introduction, bonus chapters, and even an invite to a philosophy dinner at my bookstore, The Painted Porch—​check out all the bonuses here​).

When Edward Gibbon finished ​The Decline and Fall of the Roman Empire​, he noted his sadness at taking “everlasting leave of an old and agreeable companion.” I don’t feel exactly that way—virtue isn’t something you ever finish or take leave of—but there is something bittersweet about drawing these books to a close.

I’m better for having written them—not just as a writer, but as a person. Of course, I can already see all the things I’d do differently if I were starting over, all I’ve learned since publishing the first book in 2021. But, that’s kind of the point. To get better as you go. To learn from your time here. To put your past self to shame.

One thing I’ve noticed? I am calmer. I am quieter. I argue less. I get upset less. I admit I am wrong more often. There’s still a long way to go, but I’m proud of the progress I’ve made.

That’s how Aristotle described virtue—as a kind of craft, something one gets better at just as one would get better at any skill or profession. “We become builders by building and we become harpists by playing the harp,” he writes. “Similarly, then, we become just by doing just actions, temperate by doing temperate actions, brave by doing brave actions.”

Virtue is not something you demand of others. It’s not a standard you pass laws about or police. It’s not something we flippantly say or conflate with “success.”

It’s something you demand of yourself. It’s something you do. It’s something you use day to day, moment to moment. It’s something that steers the choices you make and the actions you take. It’s something you choose.

And every situation—big and small, positive or negative—is an opportunity to make a virtuous choice.

Will you be ​brave​ or afraid? Selfish or ​selfless​? ​Strong​ or weak? ​Wise​ or stupid? Will you cultivate a good habit or a bad one? Courage or cowardice? The bliss of ignorance or the challenge of a new idea? Stay the same…or grow? The easy way or the right way?

Is it easy to make these choices? Of course not. That’s why I put it in the title of the new book—​it takes work​.

I finished the ​Stoic Virtues Series​, but I remain committed to the work.

I hope you do the same.


With the upcoming release of ​Wisdom Takes Work​, the team and I at Daily Stoic wanted to do something special, something we’ve never done before—a limited edition collector’s set of all four books in the Stoic Virtues Series. Each set is signed and numbered with a unique title page identifying them as part of the only printing of this series. I’m also throwing in one of the notecards I used to help me write the series (​learn more about my notecard system here​). There’s a limited run of these, ​so check them out here today​.

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July 30, 2025by Ryan Holiday
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