How To Be A Great Leader: Timeless Leadership Traits From Roman Emperors, Philosophers, and More

“For I believe a good king is from the outset and by necessity a philosopher, and the philosopher is from the outset a kingly person.” Musonius Rufus, Lectures, 8.33.32–34 

For thousands of years, the Stoics have not only been leaders, but the resource other leaders have turned to for advice and guidance. George Washington quoted Cato to spur and deter his troops. John Adams declared that “all the ages of the world have not produced a greater statesman and philosopher united in the same character” as Cicero. Admiral James Stockdale knew Epictetus’ works by heart and recited lines regularly. General James Mattis didn’t enter a battlefield without Marcus Aurelius’ Meditations.

How can we follow in their timeless footsteps? It’s simple. As Marcus Aurelius put it, “Go straight to the seat of intelligence.” That is exactly what this piece aims to do. You can click the links below to navigate to a specific section or scroll and read the entirety of the page. At the bottom, we’ve compiled a comprehensive list of additional resources. So bookmark this page and return to it frequently—it is the ultimate guide on leadership.

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I. What Is Leadership?

II. What Makes A Great Leader? (The Virtues of Great Leadership)

III. What Do Great Leaders Do? (According to the Philosophers)

IV. What Mistakes Do Leaders Commonly Make? (According to History)

V. Who Are Famous Stoic Leaders?

VI. What Leadership Books Should Leaders Read?

VII. What Are The Best Stoic Quotes on Leadership?

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I. What Is Leadership?

It’s a simple question, yet for all of history, the answer has frequently been wildly misperceived to disastrous ends. We can think of the Neros and the Caligulas and the Julius Caesars and the Harvey Weinsteins and the Mary Tudors and the Elizabeth Holmes of the world. They are just to name a few among a long list of powerful people who conflated “leader” with “tyrant”. 

Seneca wrote extensively on leadership and how easy it is for any position of power, if not checked by strong principles and purpose, corrupts and ruins people. They fall victim to the maxim that was supposedly a favorite of Caligula: “Let them hate, provided they fear.” How corrupted was Caligula? Well he declared himself a god and used treason trials to eliminate unabiding enemies, real or imagined (he declared war against the sea and ordered his troops to attack the waves with their swords). Seneca points to him in multiple essays and letters as a warning, as an example of everything wrong with bad leaders. They think that the way to lead is through fear. That the way to get people to do what you say is through intimidation, physical or otherwise. They define leadership as having a strong grip on their followers, as having absolute power, as having a legion of people who fear them. 

Leadership is not about power or authority or dominance. If they don’t like me, you’ll commonly hear parents and bosses say, that means I’m doing my job. No, it means you’re a tyrant. It means you’re a bad leader. “Which teacher is more worthy,” Seneca liked to ask, “the one who savages his students if their memory fails or their eye clumsily falters when reading, or the one who prefers to correct and teach with admonitions that bring a blush to the students’ cheeks? Show me a brutal tribune or centurion and I’ll show you one who makes soldiers desert—pardonably.” 

Dwight Eisenhower, one of the most successful generals and world leaders in history (who freed Rome from a modern day Caligula, by the way) defined leadership in terms that Seneca would have nodded in agreement with. “Leadership,” Eisenhower said, is “the art of getting someone else to do something that you want done because he wants to do it, not because your position of power can compel him to do it, or your position of authority.” It’s Marcus Aurelius writing patiently about considering the times he messed up, of trying to give others the benefit of the doubt, of giving them the same clemency and patience we grant to ourselves (some believe that the famous equestrian statue of Marcus pictured him doing precisely that). It’s Augustus pardoning Lucius Cinna, his top consul who conspired to overthrow him. Lucius became Augustus’s “most grateful and loyal adherent,” Seneca reports. “And no one ever again formed any plot against him.” It’s even Seneca: patiently tutoring a man who was clearly deranged, writing essays to try to steer his young charge away from ego, hoping to temper his worst impulses and steer him toward goodness. 

Whether we’re a CEO, a coach or a parent. We’re trying to get people to go along with our plans, to get on board with our vision, to execute a task we need them to do. Very little is done effectively by force. No one who is made to feel small is spurred to do great things. That’s why the great Stoics were such successful leaders. They led by example. Through persuasion and logic. From the front. With collaboration and empathy. To lead by fear is to do wrong by others and ultimately to yourself. It’s to undermine the dignity of those you serve as well as the position you hold, whatever that is.

II. What Makes A Great Leader? (The Virtues of Great Leadership)

Courage

“Remember this principle when something threatens to cause you pain: the thing itself was no misfortune at all; to endure it and prevail is great good fortune.” — Marcus Aurelius

In the winter of 1824, things were not looking good for Simon Bolivar. He was at one of the lowest points of his decade-plus long revolution of South America. Many of the countries he had freed from Spanish rule were in chaos or at risk of being re-conquered. His own health had begun to fail from so many hours in the saddle on campaign. He was haggard and gaunt—skeletal, really. A man asked Bolivar, as it appeared that he neared rock bottom, “What will you do now?” The great liberator didn’t pause, he didn’t hesitate. All his charisma returned in an instant and he answered simply and definitively, “Triumph!”

It’s one of those scenes from history that sends chills down the spine. It’s Napoleon shouting, “There will be no Alps!” It’s the Spartans retorting to the Persians who claimed the arrows of their overwhelmingly superior forces would blot out the sun, “Then we shall fight in the shade.” It’s Churchill, “We shall go on to the end…we shall fight on the seas and oceans, we shall fight with growing confidence and growing strength in the air, we shall defend our Island, whatever the cost may be…we shall never surrender.” 

The essence of Stoicism—and the mark of a great leader—is how we deal in the moments when Fate deals us a bad hand. A Stoic, Nassim Taleb has said, is a person who says “Fuck You to Fate.” It’s that hard-as-nails, I’ll-never-bow-to-you self-control that defines Stoicism—just as it defined Bolivar, Napoleon, the Spartans, and Churchill. They didn’t give in. They didn’t bend. They prevailed and conquered. 

To the Stoics, courage was the greatest of the virtues. And the history of the Stoics is replete with inspirational examples of resolve and resilience, sacrifice and courage. Cato challenging Caesar. Seneca bravely facing Nero’s end. Agrippinus refusing to attend Nero’s summons. Thrasea sticking his neck out—literally—to put a spotlight on Nero’s tyranny and losing it as a result. Marcus Aurelius staying in Rome despite the plague.

The most important virtue all great leaders possess is courage. As Nassim Taleb says, courage is the only virtue you can’t fake.   

Courage is everything. Courage in the face of the enemy. Courage to risk yourself and your safety. Courage to speak the truth. Courage to stand alone. Courage to try the difficult thing, even if it might not work. Courage to change your mind. Courage to defend something on principle. Courage to do what’s right. 

How do we get it? That takes courage too. Seneca wrote that only the prize fighter who has been bloodied and bruised—in training and in previous matches—can go into the ring confident of his chances of winning. The one who has never been touched before, never had a hard fight? That’s a fighter who is scared—and should be. Because they have no actual idea how they’re going to hold up. 

Only in “times that try men’s souls,” Thomas Paine wrote about in The American Crisis at one of the darkest points of the Revolution, can we find—and unlock—within us a “cabinet of fortitude.” The Stoic version of this idea was the Inner Citadel—a fortress of fortitude—that could be drawn on for strength in difficult times…if it had been properly stocked and built in good times. That’s what the study of philosophy was about to them. It was so when the worst that could happen did happen, they didn’t turn inside to their cabinet of fortitude, their inner citadel, and find it empty. 

It won’t be easy—it never is—but that’s the point. That’s what it takes to be a great leader.

Temperance

“Most powerful is he who has himself in his own power.” — Seneca

It’s easy to look at the great leaders and assume that their disposition comes naturally to them, or that it is somehow divinely inspired. How were they always so cool under fire? How were they always so self-disciplined? The Lincolns and Washingtons of the world—they simply don’t have to struggle with the temptations or the frustrations that we mere mortals struggle with—that’s why they are able to stand before us as models of equanimity and poise. 

Perhaps in some cases this is true, but usually it’s not. As Martin Luther King Jr. once put it, “There is something of a civil war going on within all of our lives.” Let’s take George Washington. To the people who encountered him, he was a paragon of rationality and self-control. But those who really knew him understood that he, like all ambitious people, was subject to great passions and a roiling temper from his earliest days. Indeed, this was exactly what made Washington so impressive to those who actually worked with him. As the Governor Robert Morris wrote of Washington, it was with these passions that Washington waged “his first contest, and his first victory was over himself.” 

The same was true of Cato and Marcus Aurelius. They were not naturally stoic. If they had been, their example would not be nearly so meaningful. Because then they wouldn’t have been examples at all: it would just be biology or divinity or random luck. Marcus’s Meditations is not preaching…it’s a workbook intended almost solely for the writer himself. Cato was not perfect. His peers saw in him all the same flaws they saw in themselves—but they were inspired by the way he got closer to victory than they had. He pushed them to be better. (Seneca, on the other hand, was a better writer than either one…but far less victorious). 

As leaders, we face the same inner-contest as Washington. We have ambitions. We have passions. We have tempers. We have temptations. But what matters is: can we rise above them? Can we channel them to positive ends? Whether that’s forming a new nation or leading one, being kind when it’d be easier to be mean, resisting the impulse of ego or selfishness, we can conquer ourselves and thus make the world a better place. Being provoked, only to ignore it. Being under incredible pressure and performing despite it. Overriding your fears and physical limitations in service of others. Not getting swept up in the passions of the crowd. This, we know, is self-control par excellence. And it’s victory that starts at home. It starts inside. And make no mistake, it is a battle that is as difficult to win as it is to fight. 

Dignity

“The tranquillity that comes when you stop caring what they say. Or think, or do. Only what you do. (Is this fair? Is this the right thing to do?)” — Marcus Aurelius, Meditations, 4.18

In a conversation on “You Made It Weird with Pete Holmes” about Martin Luther King Jr., the screenwriter and director Adam McKay talked about the distinction between two words (and concepts) that people commonly conflate: “Have you noticed the difference between dignity and respect is a big one? People that fly off the handle and get angry too much always talk about, ‘I’m not being respected.’ But respect is something you can’t control, right? Dignity is inside you, dignity is yours.” To the Stoics, the two big categories that everything had to be sorted into were the things that were up to us and the the things that are not up to us. Although it is nice to be respected, that really isn’t something that is up to us. But acting with dignity? Maintaining our own standards—our self-respect? That’s ours. Always. Even when we are under duress, facing adversity, or someone is attempting to humiliate us—dignity remains firmly in our control, provided we don’t give it up. 

“If you are ever tempted to look for outside approval,” Epictetus said, “realize that you have compromised your integrity. If you need a witness, be your own.” This was something Marcus Aurelius wrestled with more than Epictetus because he was a public person. He saw crowds cheering him in the street. People flocked to court to heap praise on him (before asking for favors). He also had to put up with their jeers and criticisms. 

Eventually he realized that he couldn’t pay attention to any of it. He had to hold himself to his own standard—an inner scorecard—and ignore everything else. The clapping was meaningless. The boos were too. What mattered was his own integrity, his dignity—he had to be his own witness. “Just that you do the right thing,” he reminded himself, “The rest doesn’t matter. Cold or warm. Tired or well-rested. Despised or honored. Dying…or busy with other assignments.”  

This is what made Cato such a towering figure to Seneca and Marcus Aurelius and generations of Stoics. He didn’t care what other people thought about him, what they said to him, what they did to him. Sometimes public opinion lined up with his moral compass, sometimes it didn’t, but he never let that sway him from following what really mattered. Even when they showered him with curses or tried to kill him, he stuck fast. As McKay would go on to say in that interview, while we “can’t really control what they’re doing…we can control how we react.” That’s what great leaders do. They just do the right thing. Whatever the circumstances. Whatever the risks. Whatever the reasonable excuses may allow for. They ignore all that and do the right thing. 

Because the right thing is all that matters. 

Humility

“Keep in mind how fast things pass by and are gone—those that are now, and those to come. Existence flows past us like a river: the “what” is in constant flux, the “why” has a thousand variations. Nothing is stable, not even what’s right here. The infinity of past and future gapes before us—a chasm whose depths we cannot see. So it would take an idiot to feel self-importance.” — Marcus Aurelius, Meditations, 5.23 

One of the most haunting moments in all of literature is the moment when King Lear hits rock bottom. He has destroyed his kingdom. He has lost his family. He has lost his sanity. 

He says to Gloucester as they stand on a cliff:

“They told me I was everything. ‘Tis a lie, I am not ague-proof.”

In short, all the illusions of the king have been shattered, his ego destroyed. Everything he had worked for was gone, and all that was left was the inescapable conclusion that it was his fault. He had believed the flatterers and let power go to his head. Then, after unbelievable folly and meanness, it all came crashing down. 

This temptation to believe that we are everything, that we are immune to the constraints or flaws of other people is the source of so much pain and misery in the world. Pain for the believers and for the bystanders who become its collateral damage. Which is why the Stoics—particularly the ones who found themselves in positions of leadership—spent so much time working on their egos. Marcus Aurelius actively practiced his philosophy so that he would not be corrupted by his absolute power. He talked about avoiding the stain of “imperialization”—the ego that would come from being emperor and having power. He talked about the foolishness of trying to make yourself remembered for a thousand years or of thinking you’ll live forever. Seneca wrote essays to Nero to try to steer the young man away from ego, to tell him: You are not everything. 

Or as Lane Kiffin puts it, “It’s not about me.” After helping lead USC to two national championships, Kiffin was offered the head coaching job for the Oakland Raiders, becoming the youngest head coach in NFL history. To put it lightly, it didn’t go well. In reflection, Kiffin compared himself to the Hollywood musicians and actors who “are given too much in life too soon and they’re not fully prepared to handle that, and their ego destroyed them.” Kiffin picked up the pieces and has reestablished himself as one of the great college football coaches. How? “I’ve learned,” he said, “that ego is the enemy, thanks to the author Ryan Holiday.”

Ego is the enemy. Of what we’re trying to accomplish. Of the leaders we’d like to be. Of relationships. Of kindness. Of leadership. We can’t take or receive feedback if we are incapable of or uninterested in hearing from outside sources. We can’t recognize opportunities—or create them—if instead of seeing what is in front of us, we live inside our own fantasy. Without an accurate accounting of our own abilities compared to others, what we have is not confidence but delusion. How are we supposed to reach, motivate, or lead other people if we can’t relate to their needs—because we’ve lost touch with our own?

 

The Greeks knew that hubris—ego by another name—was the ultimate enemy. That it must be conquered. That humility and self-awareness were where true strength lies. As leaders, we must remember this always, even as others puff us up or success accumulates around us. We are not everything. We are ordinary. We are mortal. We are not exempt.

Wisdom

“Mastery of reading and writing requires a master. Still more so life.” — Marcus Aurelius, Meditations, 11.29

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. 

The Stoics were learners. It’s hard to escape that conclusion when you read their writings. Marcus Aurelius begins Meditations by cataloging the lessons he learned from the many people in his life, big and small. Seneca was constantly looking at other people, studying their lives and what they did well and not so well. When Epictetus said that you can’t learn what you think you already know, he was describing his own worldview as well as the worldview of his hero—Socrates—who went around constantly questioning and putting things up to the test. 

All of them would have agreed with Emerson’s observation that we can learn something from everyone we meet, because everyone is better than us at something. In her beautiful book, Memoirs of Hadrian, Marguerite Yourcenar has Hadrian try to instill that advice in a young Marcus. He explains to Marcus that he has actively looked at the strengths of the maligned emperors who preceded him and tried to find a virtue he could take from them.

“I looked for example even to those twelve Caesars so mistreated by Suetonius,” she had him write, “the clear-sightedness of Tiberius, without his harshness; the learning of Claudius, without his weakness; Nero’s taste for the arts, but stripped of all foolish vanity; the kindness of Titus, stopping short of his sentimentality; Vespasian’s thrift, but not his absurd miserliness. These princes had played their part in human affairs; it devolved upon me, to choose hereafter from among their acts what should be continued, consolidating the best things, correcting the worst, until the day when other men, either more or less qualified than I, but charged with equal responsibility, would undertake to review my acts likewise.”

This is the attitude we must take with us, day to day, in whatever position of leadership or followership we occupy. It’s not enough to just learn from history or to be grateful to the explicit lessons we get from our teachers. We must keep our eyes open always, and actively look for opportunities to learn from everyone, including people we know are flawed or even evil. We must not let our own moral progress block us from learning from those further behind us on the road. We must always stay a student

III. What Do Great Leaders Do? (According to the Philosophers)

Great Leaders Focus On What They Can Control

There is a fascinating statue of Seneca and Nero done by the Spanish sculptor Eduardo Barrón in 1904. Even though it depicts a scene centuries after the fact, it manages to capture the timeless elements of the two men’s characters. Seneca, well into old age, sits with his legs crossed, draped in a beautiful toga but otherwise unadorned. Spread across his lap and onto the simple bench is a document he’s written. Maybe it’s a speech. Maybe it’s a law being debated by the Senate. Maybe it’s the text of his essay and warning to Nero, Of Clemency. His fingers point to a spot in the text. His body language is open. He is trying to teach.  He is wisdom embodied, hoping to instill in his young charge the seriousness of the tasks before him. 

Nero, sitting across from Seneca, is nearly the opposite of his advisor in every way. He is hooded, sitting in a throne-like chair. A fine blanket rests behind him. He’s wearing jewelry. His expression is sullen—both fists are clenched and one rests on his temple as if he can’t bring himself to pay attention. He is looking down at the ground. His feet are tucked behind him, crossed at the ankles. He knows he should be listening, but he isn’t. He’d rather be anywhere else. Soon enough, he is thinking, I won’t have to endure these lectures. Then I’ll be able to do whatever I want. 

Seneca can clearly see this body language, and yet he proceeds. He proceeded for many years, in fact. Why? Because he hoped some of it—any of it—would get through. Because he knew the stakes were high. Because he knew his job was to try, and he was going to die trying (indeed, he did) to teach Nero to be good. 

In the end, Seneca made only minimal impact on Nero, a man who was clearly deranged and had little interest in being a good emperor. Seneca lost much of his reputation in the process of working for Nero (criticism which has merit). But another way to see this exchange—and perhaps that’s what Eduardo Barron intended—is that it’s an illustration of a Stoic lesson: You can lead a horse to water, but you can’t make them drink. You control what you do and say, not whether people listen. This, Epictetus said, was our chief task: to determine what was in our control and what isn’t. The two-thousand-year-old Stoic phrase: “ta eph’hemin, ta ouk eph’hemin.” What is up to us, what is not up to us. And what is up to us? Our emotions. Our judgments. Our creativity. Our attitude. Our perspective. Our desires. Our decisions. Our determination.

All a leader can do is show up and do our work. And we have to keep showing up, even if we are rebuffed, scorned, or ignored. You gave them very careful instructions, which they disregarded to costly consequences? You find out your top employee is taking a new job? You hear that your computers just deleted a year of hard work? You’re informed that the competition just announced their groundbreaking innovation? None of that is fun. And none of that is in your control. You can let it crush you. You can fall to your knees and tear out your hair. Or you can shrug it off, and return to your chief task of discerning what’s inside your control and what isn’t, then focus all your energy on making the right choices in regards to what’s yours to decide. 

Great Leaders Never Act Rashly

When Julius Caesar was murdered in 44BC, the Roman Republic bled out with him and what emerged was the Roman empire, led by a singular man: Octavian, Caesar’s nephew. He had been studying in Apollonia (modern-day Albania) under the famous and widely respected Stoic teacher Athenodorus when Julius Caesar was killed. When Octavian returned to Rome, Athenodorus followed closely behind him. It was the job of a tutor like Athenodorus to develop in his charge the penetrating mind and leadership capabilities required for leadership. At the core of his teachings? A leader must always keep their head. Once, when asking to be relieved of his duties so that he might return to his home, Athenodorus offered one last piece of practice advice to the emperor—something he wanted him to always follow. “Whenever you feel yourself getting angry, Caesar,” Athenodorus instructed, “don’t say or do anything until you’ve repeated the 24 letters of the alphabet to yourself.” 

It is inevitable that we will be provoked in life. As leaders, we are going to find ourselves in situations where we are tempted to lose our head. We’ll be called upon to lay down the law. We’ll have to fire people. We’ll have to dock people’s pay. We’ll have to decide not to do business with someone because they’ve lied to us, insulted us, or shown a side of themselves we didn’t know was there.

Some of us recoil from this uncomfortable reality, others love it. They like the feeling of that power, maybe even a little too much. Regardless of where you are on that spectrum, you would do well to remember Athenodorus’ advice. And Seneca’s—who studied Athenodorus’s example and is the source for much of our knowledge about his teachings—about the importance of rational, deliberative thinking. As he reminds us

“A punishment that’s delayed can still be imposed, but once imposed, it can’t be withdrawn.” 

This is a trademark of great leadership. Don’t be rash. Don’t rush in. Don’t let your emotions dictate your thinking. Our words can’t be unsaid, so we should think carefully before we say them. Our actions can’t be undone, so we should be cautious before we take them. We should delay. We should recite the alphabet to ourselves. Life is unpredictable, so our responses must be measured and purposeful. 

That’s what a good leader does (and teaches in so doing). 

Great Leaders Always Look For Teachable Moments

On the eve of the 2008 election, the journalist Joe Klein asked Barack Obama how he’d made his decision to respond to the brewing scandal about Obama’s pastor, Jeremiah Wright, having made controversial statements about the government and terrorist attacks. Whether you were upset by that situation or not, whether you think he properly addressed it or not, the mindset that Obama explained to Klein is worth spending a few minutes thinking about: 

“My gut was telling me that this was a teachable moment and that if I tried to do the usual political damage control instead of talking to the American people like an adult—like they were adults and could understand the complexities of race, that I would not only be doing damage to the campaign but missing an important opportunity for leadership.”

From this, a beautiful and important speech about race relations—known as the “A More Perfect Union” speech—came into existence. A rather ordinary political scandal became a teachable moment. “If they’ve made a mistake,” Marcus Aurelius wrote, “correct them gently and show them where they went wrong. If you can’t do that, then the blame lies with you. Or no one.”

It was Andy Grove, former Intel CEO, who observed, “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.” In the 1960s, IBM CEO Tom Watson called an executive into his office after his venture lost $10 million. The man assumed he was being fired. Watson told him, “Fired? Hell, I spent $10 million educating you. I just want to be sure you learned the right lessons.” There are thousands of books about successful companies but virtually none about the lessons to be learned from those that crash and burn. 

That is the duty and goal of great leaders—they take the ordinary, frustrating, complex, difficult, and surprising situations that life throws at them and turns them into something. They never miss an important opportunity for leadership—internally or externally. They are always getting better and stronger, no matter what happens. It is part and parcel with Amor Fati. It is what it means to say that the obstacle is the way and then to take the first steps in that direction.

There is something to teach and something to learn with every moment. There is something to do with every moment. If you’re brave enough, strong enough, committed enough to eschew the path of least resistance—the damage control path—and engage these moments like a leader.

Great Leaders Have Range

If you look at any of the great leaders, you’ll notice that they had a diverse many interests. Marcus Aurelius had the most important job on the planet, but he also loved to read and write about philosophy, and enjoyed wrestling, boxing, and hunting. Seneca was a philosopher and a playwright and a political advisor. Posidonius made breakthroughs in natural history, astronomy, meteorology, oceanography, geography, geology, seismology, ethnography, mathematics, geometry, logic, history, and ethics…while working as a political advisor and military strategist at the highest level. Churchill wrote over forty books, painted more than five hundred paintings, learned and loved the slow, methodical process of mixing mortar, troweling, and laying bricks…in between his serving as prime minister of Britain.

They all, David Epstein would say, had “range.” In his book Range: Why Generalists Triumph in a Specialized World, Epstein put to bed the myth that going all in on a particular field is the key to lasting success. As he told us in our interview for DailyStoic.com:

We miss out on wisdom if we’re too narrow…Specialists become so narrow that they actually start developing worse judgment about the world as they accumulate knowledge…Breadth of training predicts breadth of transfer. Transfer is your ability to take knowledge and skills and apply them to a problem or situation you have not seen before. And your ability to do that is predicted by the variety of situations you’ve faced…As you get more variety, you’re forced to form these broader conceptual models (in the classroom setting called “making connections” knowledge), which you can then wield flexibly in new situations. 

One can imagine Marcus Aurelius’s real world responsibilities provided insights for his philosophical studies and vice versa. Or Posidonius translating things he learned from his reading and journaling into lessons and advice for his advisees. Or Churchill discovering something about himself during his manual labors. As for Seneca, his philosophy influenced his politics and his bloody and dark plays are undoubtedly influenced by what he experienced walking the halls of power.

The more things we open ourselves up to, the more we experience, the better leaders we’ll be. Great leaders don’t only open themselves up to the opportunity of being a little outside their comfort zone, they seek it out. They study subjects outside their field. They make time to pursue curiosities seemingly unrelated to their profession. They take up hobbies that challenge them both physically and mentally. Then they take that new knowledge and those new skills, and apply and wield it in their leadership role. 

Great Leaders Read To Lead

“Far too many good brains,” Seneca said, “have been afflicted by the pointless enthusiasm for useless knowledge.” He spoke critically of literary snobs who speculated for hours about whether The Iliad or The Odyssey was written first, or who the real author was (a debate that rages on today). Leaders don’t read to spew out random trivia at the dinner table or on twitter. They read to get better! To find things they can use…in their real lives. Seneca’s point was that only knowledge that does us good is worth knowing. Everything else is trivia. When Harry Truman talks about how all leaders are readers, that’s what he means too. That’s the prescription: read what is essential—so that we might have aid to offer to a friend in pain, or a soul in crisis.

Just as Frederick the Great carried the Stoics in his saddlebags as he led his troops, or Cato proved his Stoicism by how he led his own troops in Rome’s Civil War, General James Mattis has long been known for taking Marcus Aurelius’ Meditations with him on campaign. 

“Reading is an honor and a gift,” he explains, “from a warrior or a historian who—a decade or a thousand decades ago—set aside time to write.” And “If you haven’t read hundreds of books,” Mattis says, “you’re functionally illiterate.” Channeling Marcus Aurelius, Mattis notes that human beings have been fighting and dying and struggling and doing the same things for eons. To not avail yourself of that knowledge is profoundly arrogant and stupid. To fill up body bags of young soldiers while a commander learns by experience? It’s worse than arrogant. It’s unethical, even murderous. 

Well, the same is true for much less lethal professions. How dare you waste your investor’s money by not reading and learning from the mistakes of other entrepreneurs? What is the upside of trying to figure out how to lead a sports team all on your own, and not looking for shortcuts and lessons from seasoned coaches and students of the game who have published books? There is no real job training for an emperor or the advisor to the emperor, but you can imagine both Marcus Aurelius and Seneca read heavily from and about their predecessors. The stakes were too high for them not to. 

In Mattis’ view—not unlike Seneca’s—no leader is excused from studying. Drink deeply from history, from philosophy, from the books of journalists and the memoirs of geniuses. Study the cautionary tales and the screw ups, read about failures and successes. Read constantly—read as a practice. Because if you don’t, it’s a dereliction of duty. 

If you’re looking to be a better reader—to build a real reading practice—the Stoics can help. We built out some of their best insights into our Daily Stoic: Read-to-Lead Reading Challenge. It’s more than a dozen actionable challenges that will help you elevate your game as a reader, learn how to think more critically and discover important books that will change your life. There’s videos and worksheets and all sorts of recommendations and strategies for you. It’s actionable and it will help you get a better ROI out of one of the most important ways we spend our time and enrich our minds. Give it a shot

IV. What Mistakes Do Leaders Commonly Make? (According to History)

Bad Leaders Don’t Know When Enough Is Enough

The great and virtuous philosopher Aristotle was not unfamiliar with the worlds of ego and power. His most famous pupil was Alexander the Great, and partially through Aristotle’s teachings, the young man conquered the entire known world. Alexander was brave and brilliant and often generous and wise. Still, it’s clear that he ignored Aristotle’s most important lesson—and that’s partially why he died at age thirty-two, far from home, likely killed by his own men, who had finally said, “Enough.” 

Alexander never grasped Aristotle’s perhaps most important lesson: the “golden mean.” Repeatedly, Aristotle speaks of virtue and excellence as points along a spectrum. Courage, for instance, lies between cowardice on one end and recklessness on the other. Generosity, which we all admire, must stop short of either profligacy and parsimony in order to be of any use. Where the line—this golden mean—is can be difficult to tell, but without finding it, we risk dangerous outcomes. This is why it is so hard to be great, Aristotle wrote. “In each case, it is hard work to find the intermediate; for instance, not everyone, but only one who knows, finds the midpoint in a circle.” 

Far too often, leaders fall victim to what the business strategist Jim Collins terms the “undisciplined pursuit of more.” Growing up, Tiger Woods thought of “enough” as the “e-word” — like it was an expletive, something only losers would settle for. As a champion golfer, he feared the void that would form if he no longer had the game, or more honestly, if he wasn’t dominating the game. So he played through injuries and against doctors’ orders, doing serious damage to his body that dogs him to this day.

Machiavelli would say that when overconfidence enters men’s hearts, “it causes them to go beyond their mark . . . to lose the opportunity of possessing a certain good by hoping to obtain a better one that is uncertain.” Clausewitz warned generals about the “culminating point of victory.” A point where, if blindly ridden past, flush with the momentum of winning and strength, you imperil everything you have achieved. The decision to attack one additional city, to charge after the enemy who has retreated, or to extend the battle for one more day might not just be subject to diminishing returns, it might snatch defeat from the jaws of victory. Every leader runs this risk, and often, they realize they have passed it only after it is too late.

We do not have to follow in those footsteps. We know what decisions we must make to avoid that ignominious, even pathetic end: protecting our sobriety, eschewing greed and paranoia, staying humble, constantly reminding ourselves of our goals, of what we originally set out to accomplish, so that when we get there, we know…Enough.

Bad Leaders Aren’t Prepared

In Letter XCI of Letters From A Stoic, Seneca writes about his friend Liberalis who is “in some distress at the present moment following the news of the complete destruction of Lyons by fire.” In an amount of time less than it takes Seneca to write the letter, he says, Liberalis’s hometown of Lyons was destroyed by “a fire so destructive as to leave nothing for a future fire to consume.” Deeply shocked and struck with grief, Liberalis completely lost the strength of spirit that Seneca had long admired and that Lyons desperately needed.

Seneca has a very specific reason for relaying this. It wasn’t to say ‘wow, did you hear what happened? Can you believe it? What a tragedy!’ It wasn’t schadenfreude either. There was a lesson in all this, he said. “The fact that it was unforeseen has never failed to intensify a person’s grief. This is a reason for ensuring that nothing ever takes us by surprise.” 

A CEO calls her staff into the conference room on the eve of the launch of a major new initiative and begins: “I have bad news. The project has failed spectacularly. Tell me what went wrong?” 

What?! But we haven’t even launched yet…

That’s the point. The CEO is forcing an exercise in hindsight—in advance. She is using a technique designed by psychologist Gary Klein known as a premortem

In a postmortem, doctors convene to examine the causes of a patient’s unexpected death so they can learn and improve for the next time a similar circumstance arises. Outside of the medical world, we call this a number of things—a debriefing, an exit interview, a wrap-up meeting, a review—but whatever it’s called, the idea is the same: We’re examining the project in hindsight, after it happened. A premortem is different. In it, we look to envision what could go wrong, what will go wrong, in advance, before we start. Far too many ambitious undertakings fail for preventable reasons. Far too many leaders don’t have a backup plan because they refuse to consider that something might not go exactly as they wish.

It’s one thing you can be absolutely certain of: things will go wrong. Our plans will be turned on their heads. ‘But that would never happen to me’ WILL happen to you. Seneca wrote in On Anger,  “Fabius used to say that the basest excuse for a commanding officer is ‘I didn’t think it would happen,’ but I say it’s the basest for anyone. Thinking everything might happen; anticipate everything.”

That’s why we made the premeditatio malorum medallion. It is designed to keep us prepared. We carry it in our pockets, we feel its weight, we hold it, and it strengthens us to stand ready for any possibility. The back features part of Seneca’s quote “All the terms of our human lot should be before our eyes.”  With anticipation, we have time to raise defenses, or even avoid them entirely. We’re ready to be driven off course because we’ve plotted a way back.

Think that it could happen. Anticipate everything. Have a plan ready…by making it today. 

Bad Leaders Are Swept Away By Ego

The funny thing about egotistical people is that—despite any power or wealth they might have—they are really easy to manipulate. All you have to do is tell them what they want to hear; make everything seem like it was their idea; play to their vanity and their delusions. And that’s exactly what people below the egotistical leader do. The egotistical leader is invariably swept away. 

When Xerxes, King of Persia was crossing the Hellespont in the midst of the first Greco-Persian War, he built two bridges that were quickly destroyed. He personally blamed the water for attempting to spite him–thinking that it was acting against his efforts on purpose. In response he threw chains into it, gave it three hundred lashes and “branded it with red-hot irons.” With an army of some 2.5 million men, a betting man at the time would have guessed that we’d all be speaking Persian for the rest of history. But while his men were delivering punishment to water, Xerxes was humiliated by a grand total of 300 warriors who belonged to a weird military cult called “Sparta.” Xerxes limped home in complete failure and was assassinated soon after.

This is what happens when you are so self-absorbed that you think the world is out to get you. You start to see causality where there isn’t any. You fall prey to the Animistic Fallacy not because you are stupid but because of your ego. Look at Donald Trump today. It doesn’t matter whether you agree with his policies or not—it’s hard to argue that his ego has served him well. He’s surrounded by a “team of vipers” who are constantly undermining him and stabbing each other in the back. His ego allowed him to be manipulated by partisans with extreme agendas that have little appeal to the vast majority of voters. How long it will go on, we cannot say, but it’s clear every second it continues is less and less fun for him.

This temptation to believe that we are everything, that we are immune to the constraints or flaws of other people is the source of so much pain and misery in the world. Which is why the Stoics—particularly the ones who found themselves in positions of leadership—spent so much time working on their egos. Marcus would have studied the example of Xerxes. He would have saw clearly that Xerxes’s real enemy wasn’t the Greeks, but his own raging, delusional ego. Ego is the enemy. We must sweep it away before it sweeps us away. We must cultivate a habit of humility and honesty and fairness. We must cooperate with others rather than protect our interests with paranoid possessiveness. In short, we must be good people. It’s the best strategy. It’s the only way to live and to lead.

Bad Leaders Don’t Seek Out Advice

Nero is only the most infamous of a long list of Roman Emperors who possessed some good qualities, but spiraled out of control. There’s Caligula, who declared himself a god and brought charges of treason against enemies real and imagined—he declared war against the sea and is said to have told his troops to attack the waves with their swords. There’s Domitian, who also demanded to be called a god and arbitrarily banished all philosophers from Rome (Epictetus was forced to flee as a result). And, of course, Commodus, the son of Marcus Aurelius, is one of the worst examples.

What was the fatal mistake they all made? The great ancient Roman historian Cassius Dio explains it with the story of Commodus, who “was nineteen years old when his father died, leaving him many guardians, among whom were numbered the best men of the senate. But their suggestions and counsels Commodus rejected.” More interesting though, as Dio wrote in his Roman History, “[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. 

The Roman General Scipio consulted with a Stoic philosopher, Panaetius, almost daily. Before Octavian became Caesar Augustus, he was instructed by two Stoics, Arius and Athenodorus, who continued to advise him after he became emperor. Hadrian checked in to Epictetus’s lectures. Marcus Aurelius had the Stoic philosopher Rusticus—who turned him onto Epictetus in the first place. As Robert Greene writes in Mastery, “You must follow the example set by Masters throughout the ages and find the proper mentor.”

The Stoics have a long history of serving as consigliere or strategic advisors to powerful people. And in the few instances when Stoics held supreme power, they relied on philosophers as their advisors too. Power can be blinding, and self-awareness is increasingly difficult the more successful one becomes. It’s critical for leaders to have someone they trust who can give them unbiased advice, who can see the big picture, and who can help them remain a perpetual student of the craft of serving the common good. Someone older, someone more experienced, someone who has dedicated their life to understanding the kinds of problems you will inevitably face for the first time. You can’t do it all by yourself. There’s too much at stake.

Bad Leaders Fail To Plan For When They Are Gone

Queen Elizabeth I was a remarkable woman. She was uncommon and special in so many ways. She was believed to have known nine languages. She was considered one of the best educated women of her time. She presided over many English battle victories. 

And yet in one other way, she was incredibly common…not unlike so many of us: She basically refused to think of her own mortality. Which meant she refused to plan for a successor in any form. And a queen without an heir puts the entire kingdom at risk. A ruler who doesn’t consider what comes after them is bequeathing chaos and carnage to their subjects. 

Sir Walter Raleigh, writing late in Queen Elizabeth’s life, saw this happening. He saw the Queen getting older and her options disappearing, as she grew older and grey. She was, he said, “a lady whom time has surprised.” What a great phrase! Because it describes so many failed leaders. It’s the CEO who doesn’t or can’t groom the next generation of leadership in the company. It’s the toughest part of Marcus Aurelius’s legacy—allowing his unstable son Commodous to succeed him. It was inexplicable. It was a major failing. And it was the beginning of the end of the Roman empire. 

In Principles, Ray Dalio talks about retiring from Bridgewater Associates, the company he founded and built into a multi-billion dollar business. When Dalio stepped away, in a matter of months, “problems came to a head in ways that caught us off guard.” Dalio did what great leaders do: he sought advice. The best advice, he says, came from Jim Collins, “To transition well,” Collins told him, “Put capable CEOs in place.” Dalio returned to Bridgewater temporarily to do just that and once in place, he wrote, “I will be free to live and free to die.”

Great leaders have to constantly keep in mind what Seneca told us: that old age and death aren’t this thing that lies off in the distant future. We have a duty to ourselves and others, he said, to live each day like a complete life. So great leaders keep their affairs in order because they have no idea what’s going to happen or how much time they will be given. They don’t let time surprise them. They leave nothing unfinished or unresolved. They don’t delay. They don’t deny. They anticipate everything. They make sure that little changes in their absence—whether it temporarily or entirely. 

V.  Who Are Famous Stoic Leaders?

The decline and fall of Rome, the American Revolution, the French Revolution, the Civil War, depressions, periods of strife—these are the times Stoicism has surged. And these are (just a few of) the leaders who used Stoicism in those critical periods, under incredible stress and difficulty

Marcus Aurelius

If Marcus Aurelius had his choice, he probably never would have been emperor. He wasn’t born into the emperorship, he was chosen for it by the emperor Hadrian. So, as his most thoughtful biographer Ernest Renan observed, Marcus was “deprived of the ordinary society of learned men and philosophers.”

This is what makes his reign so remarkable. Lord Acton’s line is so famous and so undeniably true that most people don’t even know that it’s a quote from a real person: Power corrupts and absolute power corrupts absolutely. Just think about what the emperors before Marcus had done: Nero killed his mother and step brothers. It is said that Claudius appointed his horse, Incitatus, a senator. Augustus (Octavian at the time) executed 300 senators. Even after Marcus, look at Commodus. His own son spent most of his time slaughtering animals in the Coliseum because he enjoyed wanton killing more than serving the state. And who could tell him to do otherwise?

Marcus  had unlimited power too. Unlimited wealth. Unlimited sycophants. But he ignored it. He didn’t give into it. He did his job instead. He stayed true to his values. He was virtuous. All of which would have been extraordinarily difficult, but in resisting it, he proved Lord Acton at least partially wrong: it is not that power absolutely corrupts, it is that power reveals the character  of those who are susceptible to corruption, who are corrupt in their bones. 

Renan believed that “the throne sometimes is an aid to virtue, and Marcus Aurelius certainly would not have been what he was if it had not been that he exercised supreme power.” By that he means that as a regular citizen, Marcus still would have been virtuous. That was his character. But it would have been much less impressive, wouldn’t it? 

The temptations and opportunities of power make his goodness shine brighter and more of an example to every leader and aspiring leader. We should remain wary of power and fame, for they are hard to resist. But if we find ourselves in the spotlight,  in a position of leadership, let us see that as both a gift and a challenge. Let us be good despite it. Let us strive to be an example for others to follow. Let power be an aid to our virtue. Let it reveal our character, and let us rise to the occasion.

Cato The Younger

There’s the old proverbial expression used to make excuses: “We’re not all Catos.” There’s Seneca telling us to “Choose therefore a Cato…a master whose life, conversation, and soul-expressing face have satisfied you…For we must indeed have someone according to whom we may regulate our characters.” There’s Dante who said, “And what earthly man was more worthy to signify God than Cato?” There’s Jimmy Soni and Rob Goodman outlining in their wonderful book, Rome’s Last Citizen, the one man who stood firm against the rise of Julius Caesar, who after nearly twenty years of courageous political leadership, and civil war, made the ultimate sacrifice to inspire resistance to tyranny by committing suicide rather than submit to Caesar’s rule.

They were all marvelling the Stoic philosopher named Cato the Younger. Rome’s—and history’s—most respected “philosopher,” who appears constantly throughout Stoic literature, despite having never written anything down. He never taught any classes. He never gave interviews. His bold and brave example is what made him such a commonly cited and quoted philosopher. We had the opportunity to ask Jimmy Soni the biggest lesson he took away from all his time examining Cato’s life:

The power of Cato’s example: He really does develop something of an immunity to other people’s feelings, opinions, to his own pain and discomfort, to anything outside his control…[Cato] willed himself into a life lived on a relatively even keel. That came directly from Stoic practices.

Cato didn’t care what other people thought about him, what they said to him, what they did to him. Sometimes public opinion lined up with his moral compass, sometimes it didn’t, but he never let that sway him from following what really mattered. Even when they showered him with curses or tried to kill him, he stuck fast. That’s just what leaders do.

George Washington 

The fact that America exists is the ultimate argument that Stoicism is not apathy and that philosophy is not mere theory. Because without Stoicism, it’s possible there would have been no revolution, no Constitution, no Bill of Rights, no land of the free and home of the brave.

George Washington was introduced to Stoicism by his neighbors at age seventeen, and afterwards, staged a reproduction of a play about Cato at Valley Forge in the winter of ‘77/’78 to inspire the troops. The play became so familiar to the people in the late 18th century that it could be quoted without attribution and everyone knew exactly where the line came from. Washington liked to quote one line in particular that must have spoken to him in that way you hear a quote or an aphorism and you think, That’s it. That’s me. That’s my philosophy for life. “Free,” he wrote in a letter to a friend, “from the bustle of a camp and the intrigues of court, I shall view the busy world ‘in the calm light of mild philosophy,’ and with that serenity of mind, which the Soldier in his pursuit of glory, and the Statesman of fame have not time to enjoy.” 

How was Washington able to lead his ragtag army to victory against such impossible odds? How was he able to endure insults and defeats and betrayals without getting upset? How was he able to see opportunities where others saw disaster? How was he able to do the right thing when so many people of his time were trapped with bad ideas? (being the only founder to free his slaves, for instance.) 

With the calm lights of mild philosophy. 

Leaders must follow this advice today and every day. It served Cato well and Washington even better. All that we see must be illuminated by the calm lights of mild philosophy. So we can see what it really is. So we don’t do anything we regret. So we can use Reason to temper our impulses and our emotions. So we can, as Epictetus said, put our impressions up to the test. Because, as Marcus Aurelius talked about, our life is what our thoughts make it, what we choose to see determines what we feel, and what we feel determines how we act. 

James Stockdale 

When Vice Presidential Candidate James Stockdale stood up before the American people and asked, “Who am I? Why am I here?”, the media and the uninformed public snickered. What was a “philosopher” doing on stage at a vice presidential debate? There is no place for that in politics—least of all his brand of “Stoic” philosophy. Unfortunately, that haughty ignorance led us to mock a hero and deprived us of a chance to bring wisdom to the political conversation.

If only those snickerers knew or remembered that, nineteen years earlier, Stockdale walked out of a Vietnamese Prisoner of War camp after eight years held captive. And that he was “recognized by his captors as the leader in the Prisoners’ of War resistance to interrogation and in their refusal to participate in propaganda exploitation.” And that, “he deliberately inflicted a near-mortal wound to his person in order to convince his captors of his willingness to give up his life rather than capitulate.” And that, when he was found and revived, the Vietnamese “abated in their employment of excessive harassment and torture toward all of the Prisoners of War.” And that, he was awarded the Medal of Honor for his “valiant leadership and extraordinary courage in a hostile environment.”

Perhaps Stockdale’s question should have been, Who are you? Why are you here?

Stockdale later remembered the moment his A-4E Skyhawk was shot down over Vietnam like this: “After ejection I had about thirty seconds to make my last statement in freedom before I landed…And so help me, I whispered to myself: ‘Five years down there, at least. I’m leaving the world of technology and entering the world of Epictetus.’” In his eight years in that prison camp, these words from Epictetus kept coming back to him: “Do you not know that life is a soldier’s service?…If you neglect your responsibilities when some severe order is laid upon you, do you not understand to what a pitiful state you bring the army?” While some of his fellow POWs tormented themselves with false hopes of an early release, Stockdale’s Stoic practice helped him confront the grim reality of his situation, without giving in to despair and depression. “This is a very important lesson,” Stockdale told James Collins as Collins tells it in Good to Great, “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.”

Indeed, a very important lesson—especially for leaders. Think about how things really are. Don’t tell yourself how you want them to be. Don’t lie to yourself as a form of motivation. Be honest. Be clear. Be realistic. If they end up being better than you expect (as things often can be), then wonderful. Enjoy the treat you’ve set up for yourself. If they end up being anything else? Well, you’re prepared now, aren’t you? Better to be pleasantly surprised than unpleasantly surprised. Better to be realistic than delusional. 

James Mattis

We mentioned General James Mattis in the “Read to Lead” section above about how he recently wrote that it is unconscionable for a military leader to be “filling body bags” while they learn by trial and error. They owe it to their soldiers, he said, to learn as much as humanly possible from the experiences of history before trying to learn on their own. 

Mattis’ reading habit has become legendary. His personal library once contained 7,000 books until he retired from the military and reduced it down to 1,000, donating the rest to marines and local libraries. “He is one of the most urbane and polished men I have known,” said retired Army Major General Robert Scales. “He can quote Homer as well as Sun Tzu.” “He was once asked which American Indian warrior he most respected,” a 2010 New York Times profile explained. “His answer was a tribe-by-tribe, chief-by-chief exposition spanning the first Seminole war to the surrender of the Lakota.” And “For most of his career,” R. Manning Ancell writes in The Leader’s Bookshelf of Mattis’ book collection, “he had packed all of them up at the end of one assignment and had them shipped to his new assignment.”

But Mattis only carried one book into battle: Meditations by Marcus Aurelius. “There can be a sense at times,” Mattis explained in a speech to cadets at the Virginia Military Institute, “that it’s the first time anyone’s dealt with something like X, Y, or Z. And certainly in combat, the reason I kept a tattered copy [of Meditations] in my rucksack to pull out at times was it allowed me to look at things with a little distance.” It’s hard to read Mattis’ words without hearing Marcus:

“To bear in mind constantly that all of this has happened before. And will happen again—the same plot from beginning to end, the identical staging. Produce them in your mind, as you know them from experience or from history: the court of Hadrian, of Antoninus. The courts of Philip, Alexander, Croesus. All just the same. Only the people different.” — Marcus Aurelius, Meditations, 10.27

“If you’ve seen the present then you’ve seen everything—as it’s been since the beginning, as it will be forever. The same substance, the same form. All of it.” — Marcus Aurelius, Meditations, 6.37

“Everything has always been the same, and keeps recurring, and it makes no difference whether you see the same things recur in a hundred years or two hundred, or in an infinite period.” — Marcus Aurelius, Meditations, 2.14

“Over and over again…the world is continually renewed.” — Marcus Aurelius, Meditations, 7.25

Constantly, Marcus was reminding himself to look at things with a little distance. He would envision the courts of his predecessors and remind himself how their names “once in common use now sound archaic.” He would envision what it would mean to be praised, to receive posthumous fame, to be remembered forever and remind himself, “everything fades so quickly, turns into legend and soon oblivion covers it.” He would envision how absurd or amazing or frustrating his life might get and remind himself, ”that all of this has happened before.” 

Marcus and Mattis became exemplary leaders after becoming intimately familiar with the lives of the greats (and not-so-greats) that came before them. And in this study they had come to know, as Marcus said, what a good leader looked like. They learned from the experiences and the follies of the earlier generations—they saw across the pages of many books why courage and justice and humility and integrity and perseverance were so important (and the perils of the opposite traits). To become a great leader, it’s crucial that you do the same. 

VI. What Leadership Books Should Leaders Read?

Meditations by Marcus Aurelius

Washington: A Life by Ron Chernow

Courage Under Fire by James Stockdale

Rome’s Last Citizen by Rob Goodman and Jimmy Soni

Stoic Warriors: The Ancient Philosophy behind the Military Mind by Nancy Sherman

48 Laws of Power and Mastery by Robert Greene

Ego Is The Enemy and The Obstacle Is The Way by Ryan Holiday

The Score Takes Care of Itself: My Philosophy of Leadership by Bill Walsh

Leaders Eat Last and Start with Why by Simon Sinek

Lean In: Women, Work, and the Will to Lead by Sheryl Sandberg

Range: Why Generalists Triumph in a Specialized World by David Epstein

George Marshall: Defender of the Republic by David Roll

Call Sign Chaos by James Mattis

How to Think Like a Roman Emperor by Donald Robertson

Want our full list of 33 Books Every Leader Should Read? PLUS 5 Things Great Leaders Do? Get The Free Guide Below

VII. What Are The Best Stoic Quotes On Leadership?

“Make sure you’re not made ‘Emperor,’ avoid that imperial stain. It can happen to you, so keep yourself simple, good, pure, saintly, plain, a friend of justice, god-fearing, gracious, affectionate, and strong for your proper work. Fight to remain the person that philosophy wished to make you. Revere the gods, and look after each other. Life is short—the fruit of this life is a good character and acts for the common good.” — Marcus Aurelius

“No random actions, none not based on underlying principles.” — Marcus Aurelius 

“No role is so well suited to philosophy as the one you happen to be in right now.” — Marcus Aurelius

“Concentrate every minute like a Roman – like a man – on doing what’s in front of you with precise and genuine seriousness, tenderly, willingly, with justice. And on freeing yourself from all other distractions. Yes, you can – if you do everything as if it were the last thing you were doing in your life, and stop being aimless, stop letting your emotions override what your mind tells you, stop being hypocritical, self-centered, irritable.” — Marcus Aurelius

“Epithets For Yourself: Upright. Modest. Straightforward. Sane. Cooperative. Disinterested…Maintain your claim to these epithets—without caring if others apply them to you or not…Set sail, then, with this handful of epithets to guide you. And steer a steady course, if you can, Like an emigrant to the islands of the blest. And if you feel yourself adrift—as if you’ve lost control—then hope for the best, and put in somewhere where you can regain it.” — Marcus Aurelius

“Ambition means tying your well-being to what other people say or do. Self-indulgence means tying it to the things that happen to you. Sanity means tying it to your own actions.” — Marcus Aurelius

“If anyone can refute me‚ show me I’m making a mistake or looking at things from the wrong perspective‚ I’ll gladly change. It’s the truth I’m after.” — Marcus Aurelius

“Keep this thought handy when you feel a fit of rage coming on—it isn’t manly to be enraged. Rather, gentleness and civility are more human, and therefore manlier. A real man doesn’t give way to anger and discontent, and such a person has strength, courage, and endurance—unlike the angry and complaining. The nearer a man comes to a calm mind, the closer he is to strength.” — Marcus Aurelius

“That which isn’t good for the hive, isn’t good for the bee.” — Marcus Aurelius

“If we judge as good and evil only the things in the power of our own choice, then there is no room left for blaming gods or being hostile to others.” — Marcus Aurelius

“There is no more stupefying thing than anger, nothing more bent on its own strength. If successful, none more arrogant, if foiled, none more insane—since it’s not driven back by weariness even in defeat, when fortune removes its adversary it turns its teeth on itself.” — Seneca

“Associate with people who are likely to improve you. Welcome those whom you are capable of improving. The process is a mutual one. People learn as they teach.” — Seneca

“Philosophy is good advice; and no one can give advice at the top of his lungs…When the aim is to make a man learn and not merely to make him wish to learn, we must have recourse to the low-toned words of conversation. They enter more easily, and stick in the memory; for we do not need many words, but, rather, effective words.” — Seneca

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