18 Things I Stole From Some of History’s Greatest Leaders

People think that leadership is something that just happens. One is anointed a leader. One is promoted to leadership. One is born into leadership. And of course, this is not the case.

“Leadership,” Eisenhower said, “is the art of getting someone else to do something that you want done because he wants to do it.” Which means that, like any art, leadership is something that has to be studied. You have to practice and develop skills. Like an apprentice, you have to get yourself in the vicinity of the greats. You have to, as Marcus Aurelius wrote of his own development as a leader, “go straight to the seat of intelligence.”

No one comes out of the womb a leader. And yet we’re all leaders in one way or another—of families, of companies, of a team, of an audience, of a group of friends, of ourselves. So there’s no one who wouldn’t benefit from learning some of the essential lessons on the art of leadership from some of history’s greatest leaders. Lessons on how to inspire people, lessons on how to survive crises, lessons on how to treat people, lessons on how to learn. These 18 by no means make a complete list, but if you implement even a couple of them, I’m comfortable guaranteeing you’ll be a better leader for it. But perhaps the first and most important lesson we learn from the leaders I talk about below is that leadership is a skill that one could refine over multiple lifetimes—so the sooner you start the better.

A Leader Is A Reader

Harry Truman famously said that not all readers are leaders but all leaders are readers—they have to be. And they certainly aren’t reading to impress people or for the mental gymnastics. It’s to get better! It’s to find things they can use. Not at the dinner table or on Twitter, but in their real lives. “One common characteristic of virtually all great leaders I have known is that they have been great readers,” Richard Nixon would write later in life. “Reading not only enlarges and challenges the mind; it engages and exercises the brain. Today’s youth who sits mesmerized by a television screen is not going to be tomorrow’s leader.” Great advice… that a reader of history also knows that Nixon did not quite live up to. In all, Nixon watched over 500 movies while in office in less than 6 years. Might he have been better served by engaging and exercising his brain? Might he have been better off if he’d had more of his assumptions challenged? A leader must learn from the experiences of others. A leader must be challenged. A leader must prepare themselves for the things they’ll only be able to experience once, by learning from the experiences of others. Because, to paraphrase the soldier-philosopher General James Mattis, it is unconscionable to fill up body bags while you get your education solely by experience, one mistake at a time. A leader must be a reader. It’s not just the best way, it’s the only way. 

A Leader Knows What They Stand For

There’s a story of Mattis, as a very senior officer, who took over guard duty on Christmas so a soldier could be home with his family. These types of gestures abound in the lore around Mattis. There’s the story of Mattis exposing himself to the elements and danger in Iraq like a common soldier and countless other incidents. With modesty, he would attribute these examples of leadership to a philosophy he picked up in his early years as a Marine. “Know what you will stand for and, more important, what you won’t stand for,” Mattis wrote. “State your flat-ass rules and stick to them.” Marcus Aurelius called them “epithets for the self.” Upright. Modest. Straightforward. Sane. Cooperative. Disinterested. Those were his non-negotiables. “If you maintain your claim to these epithets,” Marcus wrote, “without caring if others apply them to you or not—you’ll become a new person, living a new life.” That’s what Mattis believed too. He said having character is harder than having physical courage. The less disciplined, more self-centered, more power-obsessed types of people are everywhere and try everything to make you those things too. Draw the bottom line, Mattis said, remove any uncertainty, clear out the ambiguity until they don’t “come as a surprise to anyone.”

A Leader Accepts Reality On Reality’s Terms

When James Stockdale was shot down over Vietnam and taken prisoner, he knew he would be the highest-ranking POW the North Vietnamese had ever captured. That meant that at the Hỏa Lò Prison, victory for his captors was getting Stockdale to break. He was deprived and tortured and beaten and stripped of his possessions and forced to wear leg irons in solitary confinement for two of the seven years he ultimately spent in solitary confinement. But when later asked if he had it the worst in Hỏa Lò, Stockled said no. Who could have possibly had it worse? “Oh, that’s easy,” Stockdale answered, “the optimists…The ones who said, ‘We’re going to be out by Christmas.’ And Christmas would come, and Christmas would go. Then they’d say, ‘We’re going to be out by Easter.’ And Easter would come, and Easter would go. And then Thanksgiving, and then it would be Christmas again. And they died of a broken heart.” When things are hard, when things are scary, when we’re tired, when we’ve had a run of bad luck, that’s what happens: magical thinking kicks in. This will all be over soon, we convince ourselves. Great leaders resist this kind of thinking. Whether they’re facing a crisis or a downturn or a disruptive competitor or a spectacular losing streak, hope and denial and running away are never part of their strategy. As Jocko Willink told me on the Daily Stoic podcast a few months into the pandemic, the only type of people among his client base of businesses and nonprofits and military leaders who had managed to thrive were the ones who accepted the reality of the situation immediately. Unflinchingly. That’s what Stockdale said too:  “You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be.” It doesn’t matter if you’re in the Hỏa Lò Prison or the midst of the biggest economic crisis of our generation, that’s the only way through. 

A Leader Puts Everything In The Calm and Mild Light

The job of a leader, George Washington said, was to look at all events, all opportunities, all people through the “calm light of mild philosophy.” The phrase comes from the play Cato, about the Roman Senator and Stoic philosopher by Joseph Addison. In a single two week period in 1797, Washington quoted that same line in three different letters. And later, in Washington’s greatest but probably least known moment, when he talked down the mutinous troops who were plotting to overthrow the U.S government at Newburgh, he quoted the same line again, as he urged them away from acting on their anger and frustration. “It shapes and builds up the soul,” Seneca wrote of the calm lights of mild philosophy, “it gives order to life, guides action, shows what should and shouldn’t be done—it sits at the rudder steering our course as we vacillate in uncertainties…Countless things happen every hour that require advice, and such advice is to be sought out in philosophy.” 

A Leader Seeks To Serve Others

Eleanor Roosevelt said that the surest way to happiness was to seek it for others. She was referring to doing good, to being of service. It’s how she found happiness despite the tragic loss of her father, her painful childhood, her troubled marriage. And it’s how she became one of the most powerful and influential female activ­ists in history and America’s most important First Lady. She did good. She made herself useful. She sought relief for others. Marcus Aurelius said that his only job was to do works for the common good. That is: a leader’s only job is to do good. To help others. To be of service. To think less of your problems and try to help others with theirs.

A Leader Is Not Passionate 

A young basketball player named Lewis Alcindor Jr., who won three national championships with John Wooden at UCLA, used one word to describe the style of his famous coach: “dispassionate.” As in not passionate. Wooden wasn’t about rah-rah speeches or screaming from the sidelines. He saw those extra emotions as a burden. Instead, his philosophy was about being in control and doing your job and never being “passion’s slave.” The player who learned that lesson from Wooden would later change his name to one you remember better: Kareem Abdul-Jabbar. 

A Leader Knows What To Prioritize

Success, money, and power can intoxicate a leader. The great ones stay sober because they know what to prioritize. One look at Angela Merkel, one of the most powerful women on the planet is revealing. She lives in an apartment rather than a palace. She is plain and modest—one writer said that unpretentiousness is Merkel’s main weapon—unlike most world leaders intoxicated with position. Or look at Warren Buffett, whose net worth is approximately $65 billion, lives in the same house he bought in 1958 for $31,500. Or San Antonio Spurs star Kawhi Leonard, who gets around in the 1997 Chevy Tahoe he’s had since he was a teenager, even with a contract worth some $94 million. Why? It’s not because Merkel, Buffett, and Leonard are cheap. It’s because the things that matter to them are. It’s not an accident that they’ve become who they are. It’s the result of prioritizing, which allows them the freedom to pursue the things they most care about.

A Leader Sets High Standards 

Football coach Bill Walsh took the 49ers from the worst team in the league to Super Bowl champions in just three years. How? He created a culture of excellence and instilled what he called his “Standard of Performance.” That is: How to practice. How to dress. How to hold the ball. Where to be on a play down to the very inch. Which skills mattered for each position. He knew that by upholding these standards, “the score would take care of itself.”

A Leader Persists 

“Two words,” Epictetus says, “should be committed to memory and obeyed by alternatively exhorting and restraining ourselves, words that will ensure we lead a mainly blameless and untroubled life.” Those two words were ‘persist and resist.’ A leader knows that an obstacle standing in their way isn’t going anywhere on its own. A leader is in it for the long haul. Others might give up but the leader says, as Margaret Thatcher famously did: “You turn if you want to. The lady’s not for turning.” A leader knows that genius often really is just persistence in disguise.

A Leader Does The Right Thing

When the Antonine Plague hit Rome and plunged its economy, fundraising efforts began with a masterstroke of inspirational leadership. As one biographer wrote, the emperor Marcus Aurelius “conducted a two-month sale of imperial effects and possessions, putting under the hammer not just sumptuous furniture from the imperial apartments, gold goblets, silver flagons, crystals and chandeliers, but also his wife’s silken, gold-embroidered robes and her jewels.” Funerals for plague victims were paid for by the imperial state. He audited his own officials and allowed no expenditures without approval. In a crisis, people must trust that their leaders are doing the right thing and that they are bearing the same burden as the citizens—if not a greater one.

A Leader Listens To Feedback

The great ancient Roman historian Cassius Dio contrasted Marcus Aurelius’ greatness against his son Commodus’ fatal flaw. Marcus famously surrounded himself with brilliant public servants and talked about how he would gladly change if anyone could show him he were looking at things the wrong way. Commodus, on the other hand, had “many guardians, among whom were numbered the best men of the senate. But their suggestions and counsels Commodus rejected.” Dio adds that “[Commodus] was not naturally wicked, but, on the contrary, as guileless as any man that ever lived.” This innocent young man became one of history’s most wicked beings because he made the deliberate decision to reject his advisors advice and feedback. As Dwight D. Eisenhower, one of the best commanders of the last century, said of the necessity of listening to feedback: “I have no sympathy with anyone, whatever his station, who will not brook criticism. We are here to get the best possible results.”

A Leader Stands Up and Stands Out

In a famous exchange, the lesser known philosopher Agrippinus said he was spurning an invitation to attend some banquet being put on by Nero. A fellow philosopher, one who had felt inclined to attend, asked for an explanation. Agrippinus responded with an interesting analogy. He said people are like threads in a garment. Most people see it as their job to match the other threads in color and style. They want to blend in, so the fabric will match. But “I want to be the red,” Agrippinus said, “that small and brilliant portion which causes the rest to appear comely and beautiful…’Be like the majority of people?’ And if I do that, how shall I any longer be the red?” He wanted to be red even if it meant being beheaded or exiled.  Because he felt it was right. Because he wouldn’t be anything other than his true self. That’s the leader’s job. It is not to go along to get along. It is not to be another replaceable thread in an otherwise unremarkable garment. The leader’s job is to stand up. To stand out. To speak the truth. As Sam Walker writes in his wonderful book The Captain Class about the unsung leaders who have taken their teams on incredible championship runs, one of the traits great leaders share is they have “strong convictions and the courage to stand apart.

A Leader is Always Composed 

“The first qualification of a general is a cool head,” Napoleon once said. Remaining cool-headed in times of crisis and adversity is one of the most critical skills. The worst that can happen is not the event itself but the event and you losing your cool.

A Leader Doesn’t Make Problems Worse

Chris Hadfield, the astronaut, reminds us that there is “no problem so bad that we can’t make it worse” (and panicking is often a way to do that). Yet how many of us have had bosses we didn’t want to keep informed about problems because if we did, they’d only make solving them harder? Leaders have to be a source of good energy and solutions. They can’t make hard things harder—they need to make hard things easier for their employees or followers. That’s the job.

A Leader Prepares  for Chaos 

As the legendary coach Phil Jackson would explain, “Once I had the Bulls practice in silence; on another occasion I made them scrimmage with the lights out. Not because I want to make their lives miserable but because I want to prepare them for the inevitable chaos that occurs the minute they step onto a basketball court.”

A Leader Has a Guiding Philosophy

I mentioned Bill Walsh’s “Standard of Performance” philosophy above. Seahawks coach Pete Carroll is known for his “Win Forever” philosophy—the winning mindset he aims to instill in his staff and players. The great coach John Wooden had his “Pyramid of Success” philosophy. These philosophies and frameworks are critical as they codify the principles and rules by which a team will make decisions and operate on a day-to-day basis. If you don’t have a philosophy, how do you expect to know what to do in tough situations? Or when things are confusing or complicated? Being reactive is never a position of strength. It is not a position a leader should find themselves in.

A Leader Gets The Best Out Of People

Aside from Marcus Aurelius’ 3-page recount of everything he learned from his mentor, Antoninus Pius is largely forgotten by history. Ernest Renan wrote that if he hadn’t groomed Marcus so successfully, his name would today be to us what Marcus’ is. All his adult life, Marcus strived to be a disciple of his adopted step-father, to whom he saw, according to the french philosopher Ernest Renan, as the “the most beautiful model of a perfect life.” What was the most important lesson he learned from Antoninus? “This in particular,” Marcus said, “his willingness to yield the floor to experts—in oratory, law, psychology, whatever—and to support them energetically, so that each of them could fulfill his potential.” This in particular because it would have been more natural for him to have often been frustrated and disappointed with people. It’s something that lots of brilliant leaders and talented people have wrestled with through the centuries—they expect of others what they expect of themselves, so they are constantly upset and let down. We know that Marcus found a better way through. “So long as a person did anything good,” Cassius Dio wrote, “he would praise him and use him for the service in which he excelled, but to his other conduct he paid no attention.” That’s key for anyone in any position of leadership. Your standards are for you. You only control your behavior. You have to meet everyone else where they are. Get as much as you can from them and of them. See the good in them. Lean into their strengths rather than disdain their weaknesses. Focus on what is special and unique about them instead of zeroing in on the ways they are not as good as you. That’s not only the kind way to lead, it’s the only effective way.

A Leader Isn’t All About Business

Randall Stutman has been a coach to some of Wall Street’s biggest CEOs for decades. His clients have included Goldman Sachs, Morgan Stanley and Bank of America. His consulting and advising agency, CRA, has worked with thousands of executives at hundreds of hedge funds and banks. These are people whose entire livelihood depends on them being perpetually ready to respond to the daily, hourly, sometimes even minute-by-minute volatility of the world’s financial markets. Stutman surprised me when he told me that he often asks these very busy executives how they recharge, given the all-consuming nature of their work. The best, he found, have at least one hobby that gives them peace — things like sailing, long-distance cycling, listening quietly to classical music, scuba diving, riding motorcycles, and fly fishing. There is a surprising commonality between all the hobbies: An absence of voices. For leaders, people who make countless high-stakes decisions in the course of a day, a couple hours without chatter, without other people in their ear, where they can simply think (or not think), is essential.

P.S. On Monday, we announced what is the longest and most in depth course ever built over at Daily Stoic. It’s one I’ve been working on for 6 months, The Daily Stoic Leadership Challenge: Ancient Wisdom For Modern Leaders. It features 63 total emails, packed with the best wisdom from the Stoics on what it takes to become a great leader. I also assembled some of today’s great leaders to be for you what Antoninus was for Marcus, as I mentioned above. Once a week, there will be a Leadership Deep Dive—a live video session where I’ll be interviewing a guest with expertise on that week’s theme before we open it up to questions from course participants. Randall Stutman is actually one of those leadership experts. He’s been a coach and a mentor of mine over the years, so I’m excited to be able to bring him—as well as military generals and pioneering businesswomen and CEOs of professional sports teams, among others—into the Daily Stoic community. I’m really excited about this course. I think it’s going to be one of our best. I would love to have you join us—you can learn more at dailystoic.com/leadershipchallenge


Written by Ryan Holiday
Ryan Holiday is the bestselling author of Trust Me, I’m Lying, The Obstacle Is The Way, Ego Is The Enemy, and other books about marketing, culture, and the human condition. His work has been translated into thirty languages and has appeared everywhere from the Columbia Journalism Review to Fast Company. His company, Brass Check, has advised companies such as Google, TASER, and Complex, as well as Grammy Award winning musicians and some of the biggest authors in the world. He lives in Austin, Texas.