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. 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 essential leadership principles from some of history’s greatest leaders. These 24 by no means make a complete list–that’s why we built The Daily Stoic Leadership Challenge (registration is currently open for this year’s LIVE 9-week course) 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. 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. 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 Puts Everything In The Calm and Mild Light. In Thomas Rick’s wonderful book Waging a Good War, he looks at what made Bob Moses one of the best (yet lesser known) of the civil rights leaders. Moses was quiet and calm. He did not seek out the spotlight. He did not make decisions out of emotion. Instead, Ricks says, quoting a colleague of Moses, he had a “‘capacity for reflection and distance from the thing that you are very much in the midst of and even leading.’” The job of a leader, George Washington similarly said, is to look at all events, all opportunities, all people through the “calm light of mild philosophy.” As leaders, we will have good days and bad, moments of heartbreak and bad luck, as well as strokes of good fortune and good timing. What matters is how we respond to these swings of fate. (That’s why we dedicate week two of The Daily Stoic Leadership Challenge to mastering your emotions.)
A Leader Always Looks For Teachable Moments. In the 1960s, IBM CEO Tom Watson supposedly 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.”
A Leader Finds A Teacher. Eisenhower was mentored by George Marshall and Fox Conner (and learned a lot about what not to do spending time under Douglas MacArthur). Marcus Aurelius spend two decades under Antoninus Pius (Hadrian had at best hoped Antoninus could offer Marcus a few years of tutoring). It was really an incredible and formative experience for him–it’s part of what we tried to distill down in the Daily Stoic Leadership Challenge, especially with the experts we brought in to talk to us. The idea is, as Marcus said of his own development as a leader, to go “straight to the seat of intelligence.”
A Leader Is Imperfect. Bad leaders think that they have to appear perfect, that they have to have all the answers, that they have to cover up their weaknesses. Great leaders do the opposite. Gandhi, once being interviewed by a reporter, said, “I am very imperfect. Before you are gone you will have discovered a hundred of my faults and if you don’t, I will help you to see them.” Why would he do such a thing? Because he knew that as a leader, egotism and an outsized sense of one’s abilities is dangerous and destructive.
A Leader Seeks Out Advice And Feedback. “It is impossible to learn that which one thinks one already knows,” Epictetus says. When a leader lets their ego tell them that they have arrived and figured it all out, it prevents them from learning and it leads to mistakes. 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 Doesn’t Tell People What To Do. Gandhi’s friends always appreciated the grace he gave them, not judging them for their choices or for the less-strict lives they led. In one of the deep dives in the Daily Stoic Leadership Challenge, General Dan Caine recounted that he has maybe given two direct orders in his entire 33 year career. Like Eisenhower said, a leader persuades, a leader motivates. A leader is a strong, inspiring example. They don’t bully and yell. They earn their authority. They are strict with themselves and tolerant with others.
A Leader Gets The Best Out of People. Lots of brilliant leaders and talented people have made the same mistake through the centuries: they expect of others what they expect of themselves, so they are constantly upset and let down. We know that Marcus Aurelius 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 Can Do Anything But Not Everything. In 1956, Harry Belafonte called Coretta Scott King. With her husband arrested once again, he wanted to check in with her and see how she was doing and what the movement might need. Except they could barely carry on a conversation, because Coretta kept being pulled away from the phone to attend to one of the children, to check on dinner, to answer the door. Belafonte politely asked why the Kings did not have any help at home. Because, Coretta said, Martin was worried other people would think he was enriching himself at the expense of the cause, living the high life while millions of blacks suffered. Belafonte was baffled, “He’s here in the middle of this movement doing all of these things, and he’s going to get caught up in what people are going to think if he has somebody helping you?” Then he said he was going to personally pay for staff—and that Martin had absolutely no say in the matter. This wasn’t just a nice gesture to an overworked family. It was also a strategic move. What Belafonte was buying Martin and Coretta was time, peace of mind, and more energy and more focus for the cause. “A leader,” Plutarch said, “should do anything but not everything.”
A Leader Prepares For The Inevitable 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 Thinks Long Term. In his 1997 letter to shareholders, Jeff Bezos said, “We believe that a fundamental measure of our success will be the shareholder value we create over the long term.” For companies—as is the case for individuals—there are always pressures to be narrow in our focus and vision. Bezos, unlike most business leaders, refused to play that game. “Rather than short-term profitability considerations or short-term Wall Street reactions,” Bezos said, the real value lies in thinking decades ahead. His maxim for business opportunities is also relevant here: “Focus on the things that don’t change.”
A Leader Prioritizes Stillness. 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.
A Leader Has a Guiding Philosophy. Football coach Bill Walsh took the 49ers from the worst team in the league to Super Bowl champions in just three years thanks to his “Standard of Performance” philosophy. 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 Always Keeps Their Cool. The journalist and author of The Chancellor: The Remarkable Odyssey of Angela Merkel, Kati Marton, told me on the Daily Stoic podcast that she once got to sneak into Merkel’s office. On her desk, there was a plexiglass cube with the words, In der ruhe liegt die kraft (“in calm, there is strength”) “Which is truly her mantra,” Marton said. “That is among her superpowers: she does not lose her cool.” Remaining cool-headed in times of crisis and adversity is one of the most critical skills. “The first qualification of a general is a cool head,” Napoleon once said. The worst that can happen is not the event itself, but the event and you losing your cool.
A Leader Stays Humble. Success, money and power can intoxicate a leader. Right before he destroyed his own billion-dollar company, Ty Warner, creator of Beanie Babies, overrode the objections of one of his employees and bragged, “I could put the Ty heart on manure and they’d buy it!” A leader benches the ego. A leader never believes they have the Midas touch.
A Leader Does The Right Thing. “Just that you do the right thing,” Marcus Aurelius told himself, “the rest doesn’t matter.” That would be his legacy, that would be his source of pride, not the buildings he erected or the conquests he made. A leader means making hard but costly decisions—like Marcus Aurelius making the decision to sell off palace jewels when the Antonine plague wiped out much of the Roman army. The people couldn’t afford to pay taxes for new troops. “So Marcus held a vast auction of contents of the imperial palace, Brand Blanshard writes in Four Reasonable Men, “and sold gold, crystal and myrrhine drinking vessels, even royal vases, his wife’s silk and gold-embroidered clothing, even certain jewels in fact, which he had discovered in some quantity in an inner sanctum of Hadrian’s.”
A Leader Seizes The Opportunity for Greatness. In early April 2020, Queen Elizabeth II gave a rare public speech with essentially that message. One of Britain’s last living links to World War II, the Queen compared it to the way she today can look back with admiration for those who acted bravely. “I hope in the years to come, everyone will be able to take pride in how they responded to this challenge,” the Queen said, “and those who come after us will say that the Britons of this generation were as strong as any. That the attributes of self-discipline, of quiet good-humored resolve, and of fellow-feeling still characterize this country.” When the Stoics say the obstacle is the way, this is what they were talking about–it’s an opportunity to be great.
A Leader Knows How to Prioritize. One of the great lessons from Eisenhower is his decision matrix that helps separate and distinguish immediate tasks from important ones. It asks you to group your tasks into a 2×2 grid deciding whether a task is either important or not and whether it is urgent. Most of us are distracted by what’s happening right now—even though it doesn’t matter—and as a result neglect what is critical but far in the future.
A Leader Makes People and Situations Better. Seneca said, “Happy is the man who can make others better, not merely when he is in their company, but even when he is in their thoughts!” That is the essence of being a great leader, a great Stoic, a great human being. As Randall Stutman told us in week one of the Daily Stoic Leadership Challenge. “At the base of leadership, what all great leaders have in their heads and their expressions is the idea that they want to make people and situations better.”
A Leader Is Rarely Surprised. Seneca said every leader needs to regularly practice premeditatio malorum—a meditation on all that could go wrong…before it goes wrong. He liked to quote Fabius: the only inexcusable thing for a commander to say was, “I did not think that could happen.” And of course, he is right: The job of the leader is to be prepared, to have a plan, to anticipate all possible and probable outcomes. Whether it’s a military campaign, a creative project, or a business negotiation.
A Leader Keeps The Main Thing The Main Thing. John DeLorean was a brilliant engineer but a poor manager (of people and himself). One executive said he was always “chasing colored balloons”—he was constantly distracted and abandoning one project for another. It’s just not enough to be smart or right or a genius. Conversely, Jony Ive, the top designer at Apple would recount how Steve Jobs was always asking Ive and other Apple employees about what they were focused on and specifically, “How many things have you said no to?” because to focus on one thing requires not focusing on other, less important things. Jobs would have liked the motto of Los Angeles Rams GM Les Snead: keep the main thing the main thing.
A Leader Trusts, But Verifies. Samuel Zemurray’s line—per Rich Cohen’s amazing book The Fish That Ate the Whale—was “Never trust the report.” He went to South America or Boston or wherever the business was being done and saw the situation for himself. He wanted first hand knowledge so as a leader he could make the right decisions. A leader can’t simply accept whatever trickles up from below them—they have to see for themselves. They have to, as the Russian proverb goes, “trust, but verify.”
A Leader Has The Courage To Stand Apart. The lesser known philosopher Agrippinus talked about how 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?” That’s the leader’s job. It is not to go along to get along. It is not to default to the status quo. 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 Assumes Formlessness. Cato, one of the most vaunted and towering Stoics, built a reputation and a career out of his refusal to compromise his principles. But Cato’s inflexibility did not always best serve the public good. Indeed, no one did more than Cato to rage against his Republic’s fall, but few did more to bring that fall to pass. Cato’s refusal to compromise was driven by moral principles but ultimately hastened the end he so dreaded. A leader learns from Cato’s fatal mistake. A leader obeys Robert Greene’s 48th law of power: Assume Formlessness. “Accept the fact that nothing is certain and no law is fixed,” Robert writes. “The best way to protect yourself is to be as fluid and formless as water.” While we admire the high integrity and uprightness of the Catos of the world, the truth is that the inflexible, uncompromising, “pure” person who cannot adjust, who cannot conceive of doing things anyway but their own, is extremely fragile.
As I said, leadership can’t be distilled down into some list. It’s a process. It’s a mindset. It’s a lifelong commitment. That’s what we’ve been trying to do for the last few years now with the Daily Stoic Leadership Challenge, our most in-depth (and most popular) course.
We designed this 9-week challenge to mirror the kind of education that produced historically great leaders like Marcus Aurelius. Specifically, we built it around one of the key lessons from Marcus’s own development: the idea that leadership is less a position and more a process.
This is our first live version of this course since 2021, so we’ve got some great leadership experts lined up for FIVE Deep Dive sessions. It’s a great opportunity to hear from some of the best, and get your questions answered.
I really hope you join us for this leadership masterclass. Registration is now open, and the course begins on September 25. Head over to dailystoic.com/lead today to enroll!
