This Was Washington’s Philosophy | Power Fades. Character Leads.

All that we see must be illuminated by the calm light of mild philosophy. So we can see what it really is. So we don’t do anything we regret. 📚 Pick up a copy of Lincoln's Virtues: An Ethical Biography by William Lee Miller at The Painted Porch | https://www.thepaintedporch.com📕 Grab copies of Doris Kearns Goodwin’s books Team of Rivals and Leadership at The Painted Porch | https://www.thepaintedporch.com🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us: Instagram, Twitter, YouTube, TikTok, and Facebook 📢 Share | ⚙️ Manage Subscription

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help you bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:14Ryan Holiday?

  You know, sometimes you hear a quote or an aphorism and think, "That's it. That's me. That's my philosophy for life." Well, it turns out that that is a pretty common and timeless thing. The very least, we know it goes back to the time of George Washington. You see, Washington's favorite play was the Play Cato, about the Roman senator and Stoic philosopher, by the playwright Joseph Addison. This play, which was written in 1712, was hugely famous in its time, and with some irony, might be called "The Hamilton of its day." It was so familiar to people in the late 18th century that it could be quoted without attribution, and everyone knew exactly where the line came from. And Washington in particular liked to quote one line

• 0:58Ryan Holiday?

  that must have spoken to him the way those quotes speak to us now, "Where you just know that nothing will capture what you think and feel about life better than that." "Free," he said in a letter to a friend after the revolution about his return to private life, "from the bustle of 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." In fact, in the book The Political Philosophy of George Washington, the author Jeffrey H. Morrison notes that in a single two-week period in 1797, Washington quoted the same line in three different letters.

• 1:42Ryan Holiday?

  And later, in Washington's greatest, but probably least known moment, he talked down the mutinous troops who were plotting to overthrow the US government. At Newburgh, and he quoted the same line again as he urged them away from acting on their anger and frustration in the calm lights of mild philosophy. That's Stoicism. That's using reason to temper our impulses and our emotions. As Epictetus said, it's about putting our impressions up to the test. It's what Marcus Aurelius talked about when he said that our life is what our thoughts make it, that what we choose to see determines how we will feel. We must follow this advice today and every day. It served Cato well and Washington even better.

• 2:26Ryan Holiday?

  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 enjoy this wonderful gift of life we possess. Whatever. Our station. Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. Happy President's Day, if that is the day you are in fact listening to this. I myself am in the middle of a big Doris Kearns Goodwin book on Theodore Roosevelt called The Bully Pulpit. And I just finished doing my note cards here in my office on a lovely book that I found

• 3:09Ryan Holiday?

  by David McCullough called History Matters. And one of the things he's talking about in History Matters that I think sort of changes how you read history is it just reminds us that the people there, they didn't know how it was going to go. No person in the past lived in the past. They lived in the present moment. And so one of the things I love to do when I read history is just think about what that person was thinking about, what was guiding them, what was influencing them. And one of those things is of course Stoic philosophy, or just this sort of traditional notion of virtue. One of my favorite presidents, not a president on most people's Mount Rushmore, not the

• 3:48Ryan Holiday?

  one that a lot of people are celebrating today, is Jimmy Carter, who I think was underrated, not just as a leader, as a thinker, he's also a great writer, but certainly a person of virtue. And I talked about this when I gave a talk at the Naval Academy, which was Jimmy Carter's alma mater back in 2024. This is what I said.

• 4:13Ryan Holiday?

  We tend to think about someone like Jimmy Carter and we would go, "Was he a great president?" Now, that's a politically charged question. That's not really what I want to get into, but I think the more interesting question is, was he a great man? And that's what I want to focus on tonight, specifically because I've been in the middle of this series of books on the cardinal virtues: courage, discipline, justice, and wisdom. And Jimmy Carter embodies each and every one of these virtues, but most of all, he embodies the virtue of justice. Courage is pretty straightforward. Discipline, we know, is required to succeed in anything. Justice seems harder to define. It's more, of course, as I said, politically charged.

• 4:57Ryan Holiday?

  It's a little more controversial, but maybe that says something about where we are as a society as well, right? When you hear this word "justice," you think the legal system, you think courts, right? You think politics, maybe you think social justice. But we don't think about it as a person with integrity, a person with a sense of honor, a person who lives by a code. Cicero would say that justice is the virtue that brings polish to all the other virtues. It's the way in which a person truly earns the title, a good or a great man. Carter embodies that in each and every way. As I've been doing this virtue series, we first talked about courage, then we talked about discipline. Tonight, I want to talk specifically about that idea of justice, justice being, I think,

• 5:41Ryan Holiday?

  the north star of the other virtues. Because if courage is not in pursuit of justice, if that discipline is not aimed towards being an effective conduit for justice, if wisdom is not teaching us right and wrong, justice, then what good is it? And so, justice is the virtue that I'm thinking about, that I wanted to talk about. The great Hyman Rickover, Admiral Rickover, class of 22.

• 6:13Ryan Holiday?

  As he would hang up the phone, as he would conclude meetings, as he would answer questions, subordinates would come to him, "What should I do? Do you think I should do this or that?" And he liked to say, "Do what is right, right? This is what we mean by the virtue of justice." He would say that life is not meaningless to a person who doesn't do things that are wrong simply because they are wrong, not whether they're legal, not whether they could get away with them. He said, "This kind of a moral code gives a person a focus, something to build a life around." And this is the virtue of justice that interests me, that we want to talk about. And we're talking about doing the right thing. We don't mean later, we mean now, right? Doing the right thing and doing it right now.

• 6:56Ryan Holiday?

  And if we go back in Jimmy Carter's life, he's born in Plains, Georgia, in 1924. It's born 100 years ago. It's amazing. He's born before the invention of penicillin. He's born before they bring sound to the movies. He remembers the most important day of his life not being his inauguration for president, but the day they flipped the electricity on. And so, it's a remarkable life spanning an incredible amount of change and incredible amount of progress. And yet, all his life, he thought back to something that his elementary school teacher, Ms. Coleman, said. She said that, "We must adjust to change in times and still hold true to unchanging principles."

• 7:40Ryan Holiday?

  And that's a beautiful idea. That's what these four virtues are, first laid down by the Stoics almost 2,500 years ago. So, she teaches him this idea that times are going to change. We're always growing and changing and adapting, but there's some things that don't change, some things that we commit to that become a part of us, that become that moral code that we live and learn by. Jimmy Carter, as a young man, hears the parable of the talents. I'm sure some of you might be familiar with this story. A talent is an amount of money. A master has three servants. He gives one five talents. He gives another two talents. And he gives a third one talent. The one with five talents invests it in the market,

• 8:24Ryan Holiday?

  doubles it. The one with two talents finds a way to put it in a bank, slowly earns interest, eventually doubles. And the third is scared of the responsibility of managing this bit of money while their master is away. So they simply bury it in the ground. They bury it in the ground. And when the master comes back, they're proud to give him his initial bit of capital. Well, the master is upset. He loves the other two. He's upset with the third. The parable of the talents, it's an accidental pun, talent being an amount of money. But it is actually a parable about talent, about our natural gifts, about what we do with our lives.

• 9:05Ryan Holiday?

  Carter would say that what he took from this story was that we should use to the fullest degree, whatever talents and opportunities we've been given, preferably for the benefit of others. Right? Each of us is unique, totally unique set of DNA that's never existed before and will never exist again. What do we do with it? What do we make of it? What good do we bring into the world through it? And I think it's this idea, actually, that brings Carter to the Naval Academy, class of 47.

• 9:37Ryan Holiday?

  It's this idea of making the most of his life, doing something, being of value, being of service, maximizing that potential that he has. But he would remember fondly, or not so fondly, every morning waking up here and being told, forced to repeat this little Naval Academy motto, "It's another week in which to excel, another week in which to excel." And so it's this idea that we always have this opportunity to be great, to become what we're capable of being if we put in the work, if we have the discipline, if we have the courage.

• 10:26Ryan Holiday?

  One of his classmates in the class of 47 was Albert Rusher. And Albert Rusher's roommate, here, committed suicide. He was devastated. He was afraid to be alone. And he would remember all of his life that Jimmy Carter, who was his classmate, invited him to come live in his dorm room. They spent three, they lived three to a room because he wanted the company. He remembered this sort of act of kindness. And I think throughout Carter's life, this is what you see, these acts of kindness, these acts of grace, these acts of support, this overflow of goodness. And it's a wonderful story.

• 11:05Ryan Holiday?

  He's also two years younger than Wes Moore, class, Wes Brown, class of 49. And you can imagine, as I think the fifth black man accepted to the Naval Academy, he would be the first to graduate, but the fifth to accept it, to be accepted. He was subjected to horrendous hazing, horrendous bullying. There was a sustained campaign to drive him out of the academy. You can imagine a young boy like Jimmy Carter, a young man like Jimmy Carter, raised in the segregated South, might have participated in this or turned a blind eye to it. But actually, they were teammates on the cross-country team. They ran together.

• 11:49Ryan Holiday?

  Carter would say later, "I ran with you and you were better." A nod to the battles that Brown had at a whole other level than Carter did. But Brown would remember a particular day. He's walking through the halls. He's being subjected to this horrendous hazing and bullying and abuse. And out of nowhere, a young Jimmy Carter comes and throws his arm around him and whispers in his ear not to let them get him down and not to let him drive him out. Now, Carter would be subjected to all sorts of abuse himself for this. He was called a traitor to his race. He was called a goddamn you-know-what lover. And he doesn't let it get to him. He's a supporter.

• 12:34Ryan Holiday?

  He's a friend. He's what today we would call an ally. And Brown would graduate in 49 as the first black man to graduate from the academy. Your field house is named after him to this day. And Carter would remember another incident like this after he enters the submarine service in 1949, 1950. He's on K-1, which would eventually become the USS Barracuda. And they pull in to the port in Nassau in the Bahamas. And the governor general invites the crew to a ball in the honor of the submariners. But he intimates that only the white officers would be allowed in, only the white crew would be allowed in. And so Carter writes about this in his memoir.

• 13:18Ryan Holiday?

  He says that the captain calls all the men together and asks them how they would like to respond. And the troops, the service having then been integrated by order of President Truman. And he would say, "After multiple curses and curse words were censored from the message, we unanimously declined to participate. The decision of the crew of the K-1 was an indication of how equal racial treatment had been accepted and relished. I was very proud of my ship." He would reflect later, when he tried to tell this story back home, that people didn't respond to it the same way. They didn't see it as a triumph. And so one of the things he took here, one of the things he was exposed to here, was a wider consciousness, a larger network.

• 14:02Ryan Holiday?

  He was exposed to people that he didn't know. And this made Carter grow and made him change. It opened something up in him that we would see flower in his career as a politician. So Carter graduates in '46. The class of '47 graduates early. And, let me see here. He famously interviews with Admiral Rickover. And as they go through the multi-hour interview, they talk about books, they talk about history, they talk about physics, they talk about mechanics. Finally, Rickover looks at him and he says, "How did you stand in your class at the Naval

• 14:47Ryan Holiday?

  Academy?" And Carter's quite proud. He says, "59th, sir." And as he goes on to talk about his academic accomplishments, Rickover stops him short and he says, "But did you always do your best?"

• 15:04Ryan Holiday?

  And this question gives Carter pause. He wants to say yes, but he stops for a second and he begins to think about the times that he didn't try his best, that he could have done more, that he could have learned more, he could have asked more questions, he could have tried harder as an athlete, could have tried harder in PT. He thinks about all the things that he didn't do, all the ways that maybe he didn't live up to that idea in the parable of the talents. And so he decides to answer honestly. He says, "No, sir, I didn't always do my best." And Rick over asks him a question that would change his life. He says, "Why not?" And then he gets up and signals that the meeting is over. And it's this question, "Why didn't I do my best?

• 15:47Ryan Holiday?

  Why hadn't I always done my best?" Would haunt Carter for the rest of his life. He would even name, when he ran for president, he would name his campaign biography after it, a nod to why not the best? Why don't we have the best? Why aren't we our best? Why don't we do our best? And I think, again, when we think about justice, it's not solely what we do for others, but first what we do for ourselves so we can be of better service to others. And Carter runs for governor in 1970. It's home state of Georgia after he's left the Navy. And it's a typical campaign for a southern politician at that time.

• 16:30Ryan Holiday?

  He gets elected, and so you can imagine his constituents, you can imagine the surprise of the media, of his donors, when the first words of his inaugural address, state of Georgia, are, "I say to you quite frankly that the time for racial discrimination is over." And it goes over about as you would expect. And yet, Carter understands that it's the right thing to do. He understands that the governor serves just one term in Georgia at that time, and now that he's been elected, he intends... Not to shirk from this responsibility, right? To do what's right and to do it right now. Of course, again, he's called a traitor.

• 17:15Ryan Holiday?

  He's called all sorts of things. But he does it because it was the right thing to do. And one of the most interesting stories, I think, of Carter's time as the governor, is the state of Georgia at that time has a work release program. And he meets a woman named Mary Prince, or Mary Prince Fitzpatrick, as she was then known, who is detailed to work the grounds of the state house. And he and his wife, Rosalynn, get to know her. They hear the details of her case. She's been convicted of murder. And they find that, in fact, she was wrongfully convicted. She was railroaded into confessing and taking a plea deal. And so they ask that she be assigned to be the nanny to their daughter.

• 18:00Ryan Holiday?

  And then they win her a pardon. And then they bring her with them to the White House. And then when he leaves the presidency, he buys her a house in Plains, Georgia. And they remain friends for as long as the two of them live. I think it's a beautiful story. Again, it's the story of a man growing, a man changing, a man reaching past the limitations of where he was born and the time he was from. I think also, though, the story of his wife, his marriage to Rosalynn, is a beautiful story. They meet while he's on leave from the Naval Academy. They marry a month after he graduates.

• 18:37Ryan Holiday?

  And they become partners in business and life and politics for a decently long time. Actually, an incredibly long time. Their marriage has its ups and downs, as all marriages do. He would wake her up each morning in the White House and say, "Just think, another day in which to excel," usually at 5:30 in the morning. And she would say, "But I don't want to excel, not at this hour."

• 19:06Ryan Holiday?

  She died last year after 77 years of marriage, the longest marriage in the history of American presidencies. In fact, 77 years is longer than half of all presidents have actually lived. It's an incredible marriage, an incredible partnership, one that I think Carter doesn't get enough credit for. I think we have to judge presidents and their marriages on a curve. The unfortunate story of great men and women of history is that their marriages are not usually love stories. There's not a ton of loyalty between them, unfortunately. One campaign reporter would say that of all the presidents he covered in the 20th century,

• 19:51Ryan Holiday?

  Jimmy Carter was probably the only one that he could say with absolute certainty was always faithful to his wife. Carter would give an interview to Playboy magazine as he ran for president. Some of the older people in the room might actually remember this. It was one of the big gaffes of his presidency. It's funny, you know, what counts as a gaffe then versus now. What Carter admits to in this interview is not infidelity, but it gives you a glimpse, I think, into what an incredibly high standard he holds himself to. He confesses to the press for looking at women with lust and committing adultery in his heart. Not in fact, but in his heart.

• 20:33Ryan Holiday?

  He's talking biblically here about having lust in one's heart. And he's not saying it in the way that I think people think. I thought it was actually quite beautiful when you actually go and read the interview. What you see he's doing is trying to say that he's not better than anyone else, that he struggles like everyone else. He says that a guy who's loyal to his wife ought not to be condescending or proud because of the relative degree of sinfulness. He was trying to think about... How hard it is to be other people. He was trying to be forgiving, give grace to other people who have made mistakes, trying not to judge, trying simply to think of his own battles and where he can do better and where he can get, where he can hold himself

• 21:15Ryan Holiday?

  to a higher standard, which I think is an important part of justice. Justice, like discipline, is a thing that starts at home. It's a thing we hold ourselves to, not other people to. It's a, it's not a weapon we wield against other people and it's not an easy road and it means being hard on yourself. That's the sense you get as you study Jimmy Carter is that no one was harder on Jimmy Carter than Jimmy Carter.

• 21:43Ryan Holiday?

  And actually, a story that most people don't know about Jimmy Carter is how he stopped a nuclear disaster, which is something that I talked about with Ed Helms. When he came on the podcast, he has a wonderful podcast called Snafu, which did a deep dive into this episode, but we talked about this story.

• 22:04Ryan Holiday?

  The Carter one I find fascinating because I, he's like one of my favorite presidents and the idea, like, he has this reputation of being this kind of like dolt or loser or weirdo. And it's like, he's a nuclear physicist who also like, single-handedly, like, in a moment of great heroism, like, saved potentially a lot of people from a nuclear disaster. And then we're just like, oh, he looks so dumb in those sweaters or whatever. Like, he said he had lust in his heart. Like, the things that we, like, that's the other thing about history is our, our, our almost impressive ability to learn the wrong thing, or to focus on the wrong narrative from a thing.

• 22:45Speaker 01

  Or reduce it to something completely irrelevant and ridiculous. Yeah, just so listeners know, this, the episode you're talking about, or the story from the chapter you're talking about is, is when Jimmy Carter was, I think, 28 years old and was, worked on in the Navy nuclear sub. I forget his title, but he had, he was high ranking in nuclear subs and, and he was called upon to address a meltdown happening in Ottawa. There was the first nuclear power plant meltdown in history. And he had to train

• 23:26Speaker 01

  They they they had, they couldn't be at the core of this meltdown for more than 90 seconds at a time.

• 23:31Ryan Holiday?

  Yeah.

• 23:31Speaker 01

  So they-

• 23:31Ryan Holiday?

  It's like some Mission Impossible shit.

• 23:32Speaker 01

  Yeah, totally. So they built this duplicate of the core, which they they then trained all of the, the, you know, specific actions that they had to do, and so they could jump in and do this thing for 90 seconds, and then jump out, and then just keep going and keep going until this reactor was fixed.

• 23:50Ryan Holiday?

  Yeah.

• 23:50Speaker 01

  And it is, uh, it's insanely heroic. Like, the danger, the, the, the pressure of something like that is, is crazy. And you're right, it is so just completely diametrically opposed to all of our popular perceptions of Jimmy Carter. It's just this, like, goober.

• 24:08Ryan Holiday?

  Yeah.

• 24:09Speaker 01

  Like, he's really, like, from the peanut state.

• 24:11Ryan Holiday?

  Yeah.

• 24:11Speaker 01

  My home state. And I love Jimmy Carter because he's like a Georgia boy.

• 24:15Ryan Holiday?

  Of course. It's also one of the greatest human beings that ever, you know, like, just a decent human being.

• 24:21Speaker 01

  Yeah. You're right. And, and, but now, but you read this, you're like, oh, he, that man was, he had grit.

• 24:29Ryan Holiday?

  Yes.

• 24:30Speaker 01

  That, that man was courageous and leadership.

• 24:33Ryan Holiday?

  Yes.

• 24:33Speaker 01

  Too, which I think a lot of people fault his presidency. That's where people are like, he was just kind of a, like, dinky president. Like, he didn't have that, that strong hand. But he, man, you look back, it's in there.

• 24:45Ryan Holiday?

  I would say, among the stories of the books, that is one of the few that gives me what you were saying, which is like, the hope, like, we got through this, like, he didn't, he was not responsible for the fuck-up in any way. He was, he was the one that helped save it.

• 24:56Speaker 01

  Yeah.

• 24:56Ryan Holiday?

  Right? And, uh, usually, we don't get such a nice, like, and that's one of the ones we know about, we don't know about it because it didn't end badly.

• 25:06Speaker 01

  Yeah.

• 25:06Ryan Holiday?

  Like, it-

• 25:07Speaker 01

  No, you're right.

• 25:07Ryan Holiday?

  So we're not, like, that, that doesn't keep anyone up at night because it was a near miss.

• 25:15Ryan Holiday?

  You heard me say at the top that Carter's one of my favorite presidents, but my all-time favorite president is Abraham Lincoln. I said I was reading Doris Kearns Goodwin's book. I've read quite a few books about Lincoln, but Doris Kearns Goodwin is one of his greatest biographers. If you haven't read A Team of Rivals, you absolutely should. She has another book that's got some great lin- Lincoln's stuff in it called Leadership in Turbulent Times. But I did a huge deep dive into Lincoln when I was writing the Wisdom book. He's the main character in Wisdom Takes Work. As I talked about with Doris, like, he's the complete man. He's one of the great men of history because not just what he accomplished, but the values that guided him there, right?

• 25:57Ryan Holiday?

  He didn't just pull off these dazzling accomplishments out of his own ambition. There was a purpose to it. And so when I interviewed Doris Kearns Goodwin, which I've been lucky enough to do twice now, we did a deep dive into Lincoln's virtues. There's also a great book titled Lincoln's Virtues by William Lee Miller that we carry at the bookstore that I love to rave about.

• 26:22Ryan Holiday?

  Lincoln's my main subject for the final virtue of wisdom. I think he is the wisest.

• 26:30Speaker 02

  Me, too. Adversity and resilience and self-reflection. I mean, he's amazing. I'm so glad. I can't believe that I haven't read Meditations in so long.

• 26:39Ryan Holiday?

  Oh, man, I'm very excited. Actually, let me just get into it right now, then, because for that chapter, I fell in love with a thing that you have as an epigraph to Team of Rivals, which you can see here, I have done my reading on. These are all pages I have marked. But I love the scene. You have it as the third epigraph in Team of Rivals, where Tolstoy, maybe you could tell the story. Tolstoy is about as far east as you can get and still be in the West, about as remote as you could get in the 20th century. And what do these distant tribespeople ask him?

• 27:18Speaker 02

  Yeah, these distant tribe people in somewhere in the Caucasus, seemingly very far away from any kind of civilization, are so excited that he's in their midst. That they ask him to tell stories of the great men of history. So he says, I loved finding this. He told a reporter this story. So he told them about Julius Caesar and Alexander the Great and Frederick the Great and Napoleon. And they seemed to love it, he said, but then they stopped him, the chief. And he said, but wait, you haven't told us about the greatest ruler of them all. We want to hear about that man who spoke with the voice of thunder, who laughed like the sunrise, who came from that place called America that is so far from here that if a young man should travel there, he'd be an old man when he arrived. Tell us of that man.

• 28:02Speaker 02

  Tell us of Abraham Lincoln. And Tolstoy was stunned to know that Lincoln's name had reached this remote corner. But then he told them everything he knew about Lincoln. And then the reporter said, OK, so what made Lincoln so great after all? And Tolstoy said, well, he wasn't as great a general as Napoleon, not as great a statesman, perhaps, as Frederick the Great, but his greatness consisted altogether in his character and the moral fiber of his being. Is that great? I mean, that's what we need in everybody, in our kids, in our, what our teachers teach our students, what our leaders should be made of. That story, I was so happy to find it so I didn't have to end with Lincoln dying. I never want them to die. They're my guys. As you know, I saw that you were calling Aurelius your guy.

• 28:44Speaker 02

  And I was thinking, oh, my God, I'll do the same thing with Teddy and Franklin and Lincoln. And I don't mean to be undifferential, just that I've lived with it for so long, like you've lived with meditations.

• 28:54Ryan Holiday?

  Yeah, you fall, you fall in love with these characters and they come to life to you. And I think that's what Tolstoy was capturing about Lincoln, which I loved so much because it is an interesting distinction. Like, all those other great conquerors, they did obviously do impressive things, but for what reason and why? And there is something, you know, modern, but then also classical about Lincoln in the sense that he didn't really do any of it for himself. Like, there was no, although he had the peculiar ambition, it was distinct from a Napoleon or any of the others.

• 29:30Speaker 02

  I really think that's right. In fact, you know, when it was, as you mentioned, the peculiar ambition was when he was 23 years old and running for office the first time. And he talks about, every man has his peculiar ambition, but his was to be esteemed of by his fellow man. And that meant somehow by doing something worthy that would be remembered over time. So that I think that that distinguishes, I mean, everybody has ambition. It's a drive for success is important for any leader or anybody to be successful. The question is, when does it become something more than the ambition for your own rise? And it becomes the ambition for the greater good. And maybe even in school, it could be the ambition for the team rather than your own glory, maybe the ambition for your state,

• 30:12Speaker 02

  for your country, for, and then for Lincoln, something even larger than that. And, and I think what it ends up being too, is that it wasn't just what he did, but who he was in the end, that's so, so impressive.

• 30:25Ryan Holiday?

  Yeah, he says somewhere that a man of ambition can, can realize that ambition by making slaves of men or by freeing slaves. And, and again, that distinction to decide to use your powers and your drive for good is sort of this crossroads moment that not all of those sort of, you know, there is something distinct about these people that become these epic historical figures, usually some profound trauma, but, but there's something about the decision to say, hey, I'm gonna, I'm gonna have a hero origin story rather than a villain origin story.

• 31:00Speaker 02

  And I think he really thought along those lines. I mean, I think the great moment when it becomes so clear is in the summer of 1864, when despite the victory at Gettysburg the year before, and the war seemingly going all right, everybody on both the North and the South was just exhausted with hundreds of thousands dead. And the Republican bigwigs come to him and say, nobody is gonna support you for the presidency in November unless you at least start peace talks. And the only way you can start peace talks is to agree that you'll put off emancipation until later and you'll just restore the Union. And he just turns them away. And he said, you know, I'd be damned in time and eternity if I returned the black warriors to slavery. And he, that meant he was really thinking he might lose

• 31:43Speaker 02

  the race. And then Atlanta falls and the whole mood of the North changes from that, you know, frustration and sadness and just desire to end the war. The mad cry for peace ends and he's able to win the war, but he wins it with emancipation and Union, both goals intact because that moment, that was the key moment when the ambition for his own victory, and he wanted to win that second term. He said, it's a, you know, it's a reaffirmation of what his first term had been all about. And he wanted to finish the war. But he wouldn't do it on the terms that would be morally wrong.

• 32:13Ryan Holiday?

  Yeah, the idea of there being a principle beneath the ambition that that doesn't get corroded or diminished as the as the ambition begins to be realized, because I think we see both ancient and in modern figures, they often did start with a reason, and then that reason falls away and is sort of just replaced with either momentum, or self-preservation, or some other force. And for Lincoln, you know, that it all kind of hearkens back to this singular experience where he watches those slaves being walked onto a riverboat,

• 32:54Ryan Holiday?

  just the black and whiteness of that being wrong, and that's staying with him always. I just, I, that's what I found, like, what good is the wisdom if it, if it isn't directed at some fundamentally moral purpose?

• 33:08Speaker 02

  Absolutely. I mean, you're right, that that vision of seeing that just made him know, as he said later, if slavery isn't wrong, nothing is wrong. It had to be wrong. And then he just had to figure out what he could do about it. That's the complication. Even with the powers of the presidency, he couldn't free the slaves until he came up with the idea that he could use his powers as commander in chief, because the slaves were giving an undue advantage to the South, so that as a commander in chief, he could free them and bring them to our lines rather than the Southern lines, and then allow that. But even then, he knew that when the war was coming to an end, that he had to then get the constitutional amendment to end slavery, because then he would no longer have the commander in chief powers to do it. So that's why it took him a while to realize that desire

• 33:53Speaker 02

  to free them. But it was always there from that moment, you rightly point out.

• 33:57Ryan Holiday?

  Yeah, that's what I, what I love about Lincoln is, is, okay, there are, there are obviously many, many principled people out there. Very rarely do they find themselves in the presidency, right? And, or in really any position of leadership or power. And, and Lincoln's wisdom wasn't just about sort of getting to the nub of it, as I think he once described, as someone once described his powers. He could wrap his head around the issue of sort of what was right and wrong. But then he had this, this very pragmatic Sense of how to get things done. I always come back to this quote from JFK, I think, who said, you know, parents want their kids to be president, but not politicians.

• 34:38Ryan Holiday?

  Like, Lincoln had the unique fusing of that, that sort of moral sense with a real ability to operate in the political sphere. And those traits tend to be mutually exclusive, it seems.

• 34:54Speaker 02

  I think you're right. I mean, he combined several different qualities. I mean, I think that was one of them. I mean, he was a very practical politician, and he knew the importance of educating public sentiment. Because as he said, in a democracy, there's nothing more important than public sentiment. It's more important than what Congress does, or the Supreme Court does. And he didn't mean just public opinion. He meant you have to really educate the country to an understanding that slavery had to be ended. And once he had done that, once he realized that that spread, he knew that it somehow it was going to end, you know, that there was a force then. That was a force that would take it along. But that, so that was a very practical sense of when he said that if he had, if he had issued the Emancipation Proclamation six months earlier, his practical politician's

• 35:37Speaker 02

  side said he would have lost the border states, and then he would have lost the war. If he'd waited any longer, he would have lost the morale boost that it provided to give the Emancipation Proclamation and bring the black soldiers into, into play. So his sense of timing came from that practical politician. But the principle was always there. You're absolutely right.

• 35:54Ryan Holiday?

  And I love the idea of, of the president calling for books about war from the Library of Congress, you know, like, like, that he also had this sort of ability to, to educate himself quickly, but then also, he manages to, to grasp the sort of central strategic issues of the Civil War better than the people actually educated in the science of war at that time.

• 36:20Speaker 02

  No, it's incredible. I mean, I think that's the great thing about his self-education. When I think about all the books that he read when he was young, and there's some of the great books he's reading, you know, I mean, when he, when he got a copy of Shakespeare, or he got Aesop's Fables, or the Bible, he couldn't eat, he couldn't sleep, he was so excited. So he educated himself in great books. And then he was able to have the humility enough. I mean, can you imagine what it was like to say at that time, I'm the president. Could I have some on the art of war? You know, you have to have a lot of confidence in yourself to not know in today's world, somebody would make fun of him. Oh, my God, he's just beginning to educate himself on this. He thinks he knows what the generals. Of course, McClellan would think he was educated far better, but he knew better than McClellan what to do.

• 37:03Speaker 02

  You're not just, you know, you're not just capturing land. You have to capture the army and decimate that as time went by.

• 37:11Ryan Holiday?

  Yeah, I mean, I think he has to check out one of Halleck's books. So he's reading books from his subordinates who are, you know, shortly thereafter briefing him. You're right that the confidence to say, on the one hand, I don't know enough about this, and then to do the work to learn about it, and then to not be bullied by this person who is, you know, objectively more educated than you or more schooled than you in the issue. Lincoln had this both humility and this confidence without it sort of seeping over into egoism.

• 37:56Ryan Holiday?

  Outside of just his principle, his character, his commitment to doing the right thing, Lincoln's also really funny. I love what a pragmatic, practical politician he is, but again, also his sense of humor. And when the writer and editor, John Avalon, was on the podcast, we talked about this as well. We also had a funny story involving Jimmy Carter and our barber. We had the same barber in New Orleans who used to rave about Jimmy Carter. That was actually why I decided to read more about him. And it turns out John Avalon had the same barber. Funny thing. Anyways.

• 38:37Speaker 03

  But the fact that Lincoln is also, the way he uses humor.

• 38:40Ryan Holiday?

  Yes.

• 38:41Speaker 03

  Is very disarming and it's a very effective political tool. We don't use as much today.

• 38:47Ryan Holiday?

  To me, I think if you're not funny, you're probably not very smart. Like, I think there's something about really smart people are under, smart and wise people understand things at such a level that they can be humorous about it. Like, he understands the humor about it. He understands the absurdity of existence, the futility of so many things, like.

• 39:05Speaker 03

  Tells a lot of stories about that.

• 39:07Ryan Holiday?

  Yes, yes. And, and also like, he has like a dirty sense of humor. Like, like, he was filthy.

• 39:13Speaker 03

  Yeah. The fascinating contradiction is that, yeah, he's got a very bawdy sense of humor, right? And he's got a complicated marriage. There's a lot of things that are, you know, he's, he's alternately, he's sunshine and shadow, right? He's alternately depressive and telling a lot of jokes, which people think are totally inappropriate at the time. Like irrelevant and beneath the chief executive at this great moment. But his point is, for him, humor is also self-medication.

• 39:35Ryan Holiday?

  Yeah. He says, if I don't laugh, I would die.

• 39:36Speaker 03

  Exactly. And that's a, that's a really powerful story where, where one of his friends visits him in the White House after a devastating defeat for the Union and finds him sitting by the fireplace laughing. And he friend launches into him and says, how can you be laughing at a time like this? And he throws the book down and looks at him with tears in his eyes and says, don't you realize that if I could not laugh, my heart would break and I would be unable to do my job?

• 39:58Ryan Holiday?

  Yeah.

• 39:58Speaker 03

  It's those moments that are so human and those moments that we need to recognize today and that belief that sort of laughter is the shortest distance between people. And humor is really disarming. Those are more things that we can cultivate. And I think when, when, when humorlessness takes root in a political movement, that's a sign that it's not going to be able to resonate.

• 40:17Ryan Holiday?

  Yes, yes. They've sucked the joy out of life and the connection out of life and the humanness out of it, too. Which I actually do think that it's kind of like, even though comedians seem to have had this kind of right wing shift, which is weird lately. Especially in the podcasting space, certainly.

• 40:37Speaker 03

  Yes, that's true.

• 40:38Ryan Holiday?

  The humorlessness of that whole scene is actually, I think, interesting. Like, they'll laugh at people, but there's a humorlessness. As like, the main victim of Lincoln's jokes was himself.

• 40:50Speaker 03

  Correct.

• 40:50Ryan Holiday?

  Like, he tells this story about a man sent to kill someone if he can find someone uglier than him, and he finds Lincoln, you know, like, he, most of the jokes are about how gangly and weird and, you know, they're all at Lincoln's expense.

• 41:05Speaker 03

  And he learned that by actually mocking somebody in the Illinois State Legislature and actually hurting the man's feelings, and he's an empathetic enough, soulful person, that he basically resolved that, you know, no, it's to break the ice and therefore self-mocking humor, but insisting on humor, you don't wield it as a weapon.

• 41:23Ryan Holiday?

  Yes.

• 41:23Speaker 03

  And that's where sort of a deeper wisdom and compassion.

• 41:27Ryan Holiday?

  There's no cruelty in it, for the most part, unless you'd say he's being cruel to himself. But yeah, there's no victims of the jokes.

• 41:34Speaker 03

  That's right. And I do think, you know, look, but we want to be on guard against humorlessness and speech codes and, you know, because that does sort of suck the joy.

• 41:43Ryan Holiday?

  Totally.

• 41:44Speaker 03

  A successful political movement, I've been interviewing folks on my Bulwark podcast about how you create a pro-democracy movement that can push back on authoritarian moments. And one of the things is, it's got to be positive and patriotic.

• 41:55Ryan Holiday?

  Yeah.

• 41:55Speaker 03

  And it's also got to have a sense of fun.

• 41:57Ryan Holiday?

  Yes.

• 41:57Speaker 03

  You know, that's necessary for a movement. People feel like they're part of something bigger themselves, but it's not a grim and humorless march. It needs to be defiant and optimistic and patriotic and inclusive, not exclusive.

• 42:08Ryan Holiday?

  Yes.

• 42:12Ryan Holiday?

  I could rave about Lincoln all day. I could rave about American presidents all day. I could rave about history all day. Here's a quick one on JFK. In October of 1962, John F. Kennedy wakes up in the White House and he's briefed by the CIA. The Russians have set up a series of ballistic nuclear missiles on the island of Cuba. Some are already assembled and more are on the way. And Kennedy has every reason to be upset, not just because this is dangerous, the world is now on the brink of nuclear war, but he had specifically talked to Khrushchev about this very plan and been assured that it was not going to happen. He'd also been diplomatically humiliated, he said, manhandled in his words, by Khrushchev at their last meeting. This was a-

• 42:56Ryan Holiday?

  Provocation. It was intended as a provocation. And had it been taken as one, though, the world could have ended like that in a nuclear holocaust. Almost every single one of Kennedy's advisers told him the only option on the table was bombing Cuba. Those were the conservative ones. The aggressive one said he had to bomb Cuba and East Berlin and Russia, right? This was a provocation, and provocation must be met with response. And Kennedy has the discipline, the perspective, to step back and say, hey, what are they gonna do after we do that? This is basic game theory. I'm gonna do X, you're gonna do Y, and I'm gonna respond, and you're gonna respond. He says, like, not only am I concerned about what they're gonna do next,

• 43:40Ryan Holiday?

  I'm concerned about seven or eight steps later in this escalation. He says, I think you guys are wrong, but I'm worried you're so wrong that no one's gonna be around to say, I told you so. And so, in what became known as the 13 Days, Kennedy does what leaders are supposed to do. When everyone else is freaking out, when a solution is not yet visible, when the worst of people's emotions are being brought out, he is a calming influence. The fact that the Cuban Missile Crisis evolves or transpires over 13 days is itself a testament to brilliant leadership. So anyways, I'll wrap this episode here. I hope you have a great President's Day. And I hope this episode reminds you

• 44:23Ryan Holiday?

  that leadership isn't just about a title. It's ultimately about character. Talk soon.

• 44:31Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us, and it would really help the show. We appreciate it, and I'll see you next episode.