Admiral James Stavridis on James Stockdale and the Voyage of Character

On today’s podcast, Ryan talks to Admiral James Stavridis about the voyage of character as detailed in his book Sailing True North, his friendship with the modern day Stoic James Stockdale, the urgency of educating yourself through books and reading, and more. Admiral James Stavridis is a retired four-star U. S. naval officer. He served for five years as the Dean of The Fletcher School of Law and Diplomacy at Tufts University. He led the NATO Alliance in global operations from 2009 to 2013 and is currently an Operating Executive of The Carlyle Group, a global investment firm. His new book 2034: A Novel of the Next World War was released in March 2021. This episode is also brought to you by Public Goods, the one stop shop for sustainable, high quality everyday essentials made from clean ingredients at an affordable price. Everything from coffee to toilet paper & shampoo to pet food. Receive $15 off your first Public Goods order with no minimum purchase. Just go to publicgoods.com/STOIC or use code STOIC at checkout. This episode is brought to you by Blinkist, the app that gets you fifteen-minute summaries of the best nonfiction books out there. Blinkist lets you get the topline information and the most important points from the most important nonfiction books out there, whether it’s Ryan’s own The Daily Stoic, Yuval Harari’s Sapiens, and more. Go to blinkist.com/stoic, try it free for 7 days, and save 25% off your new subscription, too. Today’s episode is brought to you by Munk Pack, Keto Granola Bars that contain just a single gram of sugar and 2 to 3 net carbs—and they’re only 140 calories. Get 20% off your first purchase of ANY Munk Pack product by visiting munkpack.com and entering our code STOIC at checkout. This episode is also brought to you by Ladder, a painless way to get the life insurance coverage you need for those you care about most. To apply, you only need a phone or laptop and a few minutes of time. Ladder’s algorithms work quickly and you’ll find out almost immediately if you’re approved. Go to ladderlife.com/stoic to see if you’re instantly approved today.***If you enjoyed this week’s podcast, we’d love for you to leave a review on Apple Podcasts. It helps with our visibility, and the more people listen to the podcast, the more we can invest into it and make it even better. Sign up for the Daily Stoic email: http://DailyStoic.com/signupFollow @DailyStoic:Twitter: https://twitter.com/dailystoicInstagram: https://www.instagram.com/dailystoic/Facebook: http://facebook.com/dailystoicYouTube: https://www.youtube.com/dailystoicFollow Admiral James Stavridis:Homepage: https://admiralstav.com/ Twitter: https://twitter.com/stavridisj See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:03Ryan Holiday?

  Welcome to the Weekend Edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring.

• 0:54Ryan Holiday?

  Hey, it's Ryan Holiday. Welcome to a very special episode of the Daily Stoic Podcast. I reached out to this guest through some contacts I have at the Stockdale Center at the U.S. Naval Academy. I've read his fantastic book, Sailing True North: Ten Admirals and the Voyage of Character by Admiral James Stavridis. And it's just a fascinating book. If you like my books, like The Obstacle is the Way, or Ego is the Enemy, or Stillness is the Key, where I sort of tell moral stories. If you like learning by stories, this is a fantastic book for you. He has a new novel out as well called 2034, which he's co-written with a novelist I like named Elliot Ackerman. But Admiral James Stavridis spent more than 30 years in the U.S. Navy.

• 1:39Ryan Holiday?

  He rose all the way to the rank of four-star admiral. He was the supreme allied commander of NATO. He's a fascinating thinker and writer. He was a dean at Tufts University. He's just a fascinating guy. You can tell in this conversation how much I enjoyed having it. I learned a ton from this book. I learned a ton from talking to him. And we just really get into it. It was an honor for me to have him on. It's an honor for me to talk to someone who knew the great Stoic Admiral Stockdale in person. But I think you will love this book, Sailing True North: Ten Admirals and the Voyage of Character. It's a great, diverse, interesting list. I've heard of some of the people, hadn't heard of others of the people. I'm going to do a bunch of further reading on several of them.

• 2:23Ryan Holiday?

  So here is my interview with Admiral James Stavridis, and can't wait for you to hear it.

• 2:32Ryan Holiday?

  Well, I wanted to start with the subtitle of Sailing True North, this idea of the voyage of character. Because there's something I've been thinking about that your title brings to mind that maybe you could help me get some clarity on. So the Greeks have this expression, "character is fate," right? Sort of who you are determines what you're going to do. But I think a thing that I struggle with, that I've gotten questions about from other people is like, but does that mean that it's not possible to change, right? Does that... So I love the idea of the voyage of character, because it sort of called to mind this idea that it's a journey that we're going on,

• 3:12Ryan Holiday?

  as opposed to just being this fixed thing, either from birth or early age. And yet, I do believe in the expression "character is fate." You know, what you see is what you get. So walk me through that paradox.

• 3:29Speaker 01

  I'm a believer that, just as with leaders are made not born, people of character are made not born. And I think anybody's voyage of character starts in the household. And if you're lucky enough to have parents who care for you deeply, but care enough to shape your voyage, then you'll succeed far more in that voyage of character. So it begins in the home with the example that your parents set for you. Then... I think it goes to your school, your education, your interactions with your peers and your teachers. Why is it everyone can remember one teacher who really stands out

• 4:12Speaker 01

  for them? Typically around sixth or seventh grade, Mrs. Dodge who taught history, Mr. Robinson who taught math. There's always a teacher in the story and I think that becomes the next chapter in this voyage of character. And then life explodes. Life happens when you come out of high school or college or whenever you step into life in very real ways. And I saw in your biography that you didn't finish college. You stepped into life. It kind of exploded.

• 4:44Ryan Holiday?

  Sure.

• 4:45Speaker 01

  And that's a moment of real character for anybody, whatever the circumstances, when finally you own your education. You are not at that moment being told what to read and how to curate it. All of a sudden you own that education. That's where reading comes in immensely in the building of character. I believe in books. I believe in reading to build our character. And fourth and finally, it's the circumstances of your voyage, the situations that challenge you. And whether you have a relatively easy passage in life and things tend to go very smoothly for you. Not many people like that, I don't think.

• 5:26Speaker 01

  But for most of us, there are twists and turns and moments when like Sisyphus, to go back to the Greeks, you feel like the boulder is rolling back down on you. So resilience and your ability to meet those challenges, I think, comes together with the first three things in the voyage that I just mentioned. That's how I would sketch it out.

• 5:45Ryan Holiday?

  And one of the ways I was thinking about this sort of tension between, you know, character is fate and then also that people can change. It's sort of this idea of like, you can change, but then when you're hiring someone or you're evaluating a political candidate or what, you sort of go, look, who they've been is very likely who they're going to be in the future. So, so it's sort of this idea like you, you, you force yourself to change, but you don't go around expecting an old dog to learn new tricks. That's a good way to be disappointed.

• 6:16Speaker 01

  I think that's true up to a point. In other words, we could both come up with, I'm sure, some historical figures who do have epiphanies, sometimes relatively late in life. But as a general rule, no, there are very few Saint Paul on the road to Damascus moments for anybody. Most people, I believe, their character becomes quite well-formed by the combination of the first three things I mentioned. By what happens in your home, by the education you receive, and then how you react in that explosive moment, the books you read, the experiences you have. I think your character is deeply shaped, let's put it that way, by the time you're

• 7:00Speaker 01

  in your mid to late twenties.

• 7:02Ryan Holiday?

  Yeah, we see that in sports, right? There's the athlete that gets in trouble, that gets arrested, that's been a locker room cancer on their last three teams, and then the GM or the coach says, "Well, with me, it'll be different, right? We'll get it to work." And it almost never works.

• 7:18Speaker 01

  I think that's true, and, you know, we see that in the Navy as well. And what I've always said about this is, I will give anyone a second chance, but I will never let the giving of chances hurt my ship, hurt the organization. I think that's a pretty good rule to follow. It's not three strikes and you're out, but I'm a believer in second chances, particularly having been given a few second chances myself along the road.

• 7:48Ryan Holiday?

  Well, and it's also, what's the motivation of the second chance? Are you giving the second chance out of generosity and belief and a desire to help someone? Or, as is often the case with, let's say, in sports, but I'm sure it happens in the Navy, it happens in business, you go, "Sure, this person got in trouble, sure this person did some bad things, and so they're undervalued on the market, so it'll be good for me." You know, like, they're like, "Sure, this guy has a domestic violence charge on his record, but he can sure run the ball." That's always when it comes back to bite the coach. They're trying to, you know, they're trying to, they're not trying to rehabilitate someone, they're trying to get something on the cheap, and it comes back to haunt them.

• 8:30Speaker 01

  This is absolutely true, and there's also...

• 8:34Speaker 01

  An ego on the part of the leader who, as you alluded to, says, "I can fix this." And I'll give a very practical example. When I was in my mid-30s, I was the captain of a warship for the first time, big, beautiful destroyer, about 400 people on it, marvelous, marvelous ship. I was very proud of that ship. We took the ship into my hometown, Jacksonville, Florida, for a port visit, and my chief engineer, effectively the third or fourth most senior officer, went to a bar, got drunk, lit up the whole bar, and then punched a police officer. My hometown.

• 9:13Ryan Holiday?

  Yeah.

• 9:14Speaker 01

  And, you know, I said, and it was a real act of ego, I said, "You know, I can fix this guy." Because he was very talented, and his sailors loved him, and he had a lot of charisma. But I took a chance on him, brought him back, kind of didn't put it on his record. And we got him through that tour. But here's my punchline: Three years later, on another ship, for another captain, he did almost exactly the same thing. And so I had allowed my ego to perpetuate someone who turned out to be a problem for my successor. And that is another aspect to this.

• 9:57Ryan Holiday?

  Yeah, that's fascinating. I was, I was just reading a book about Captain Bligh and Mutiny on the Bounty, and it was, it was a really interesting book, and it reminded me of this expression, "character's fate," you know. So it happens the one time, I'm sure you know the story, but it happens the one time. And then I was reading, "He gets another ship after, and the men mutiny a second time." And I was sort of thinking like, "Oh, man, yeah. If it happens to you once, it's probably not your fault. If it happens to you again, it's definitely your fault."

• 10:24Speaker 01

  I think that's right. And by the way, not everyone will want to plow through the novel, and it's actually a trio of novels, Mutiny on the Bounty, Men Against the Sea, and Pit, Karen Island. But I highly commend the film, the most recent. It's been made into a movie four times, but the best of it, I think, is the relatively recent one, simply called Bounty, and it's absolutely terrific. Couple of riveting performances, and it really explores the character of William Blythe.

• 10:57Ryan Holiday?

  Ooh, I can't wait.

• 10:58Speaker 01

  Which was complicated, to say the least.

• 11:00Ryan Holiday?

  Definitely. And I wanted to talk to you about something pertaining to that as well.

• 11:05Speaker 01

  By the way, guess who plays Christian Fletcher?

• 11:08Ryan Holiday?

  Who?

• 11:09Speaker 01

  A young Mel Gibson.

• 11:11Ryan Holiday?

  Really? Okay. Yeah, it was striking to me that the sort of the fundamental flaw in Blythe, which you write about in Sailing True North, was his temper. He sort of had a temper, and that temper is always coming back to haunt him. You have an interesting story in the book. You're talking about how collectively you and the men on the ship sort of go, men and women on the ship go, we're not going to lose our tempers at all. And you said you were sort of successful in that. I'm curious, how does one collectively manage the tempers of hundreds of people in very close quarters with each other?

• 11:48Speaker 01

  Number one, you set an example as the leader. And so, job one is you don't lose your temper. And, you know, I'm no Albert Schweitzer, I'm no Mother Teresa. I'm like anybody else. I get frustrated and upset. But I have worked very, very hard over the course of my life not to allow my emotion to override my judgment. And I have found, by observing other senior leaders who are prone to losing their temper, shall we say, that it never helps.

• 12:22Ryan Holiday?

  Yes.

• 12:23Speaker 01

  It simply injects more chaos into what is already a frustrating situation. For me, you have to, as a leader, you have to try and let time slow down and understand what's happening. And that's in combat, and it's in day-to-day operations. So, number one, it's toned and set from the top. Number two... Go to the most senior people on the ship and get their buy-in. So here you're talking about your number two called an executive officer on a Navy warship, the second-in-command, your command master chief, the senior enlisted sailor on the ship, and your department heads, typically four or five people who are the next oldest people in the crew.

• 13:05Speaker 01

  So you get their very specific buy-in, and you are ruthless about enforcing it as a culture. You call out anybody who verges into that. And then third and finally, you indicate again and again and again to the sailors that we're not going to blow up. I expect you not to blow up. We're going to figure this out together. And that narrative is very, very important to solving the problem. Again, I've found this works very well in the heat of combat, and it works very well in the day-to-day maintenance of the ship.

• 13:43Ryan Holiday?

  Yeah, I've never found, because I have a temper, and I think, I think what we're not talking about is you don't have a temper. What we're talking about is you keep it under control. George Washington loved a line from Cato. It's actually from a play about Cato, but he says, "You have to look at things in the cool light of mild philosophy." You know, you have to be able to step back and see it from a distance. But I've never found myself having lost my temper and then been like, "I'm so glad I did that." It never feels good.

• 14:13Speaker 01

  Yeah, correct, for any number of reasons. You're talking about the play that he would perform for his men.

• 14:18Ryan Holiday?

  Yes.

• 14:19Speaker 01

  Perform. Yeah, this is very elemental, and I also commend people to his, as I'm sure you're very familiar with, his Rules of Civility. That was a very small volume that I would often hand out in my various commands, up to and including when I was a four-star Supreme Allied Commander of NATO.

• 14:39Ryan Holiday?

  Got a quick message from one of our sponsors here, and then we'll get right back to the show. Stay tuned.

• 14:46Ryan Holiday?

  Yeah, again, we tend to think of these people as saints, whether you're looking at a George Marshall or a George Washington. You know, you think that, oh, that they were just saints. And it's like, no, Marshall had a horrible temper, but he said, I can't afford to lose my temper. And I think it's almost more impressive if it's a choice than if they're just naturally have that disposition.

• 15:13Speaker 01

  Yeah, well said. And Eisenhower, the same way, famously had a real temper and occasionally lost it, but could always get it back. In this regard, by the way, I love to quote what I think is the greatest book of leadership of the 20th century, which is The Godfather by Mario Puzo.

• 15:34Speaker 01

  And in the book, Don Corleone says, "Don't make the mistake of hating your enemies. It clouds your judgment." And that is so true. Again, this isn't about whether it's ethically, morally right or wrong to lose your temper. I happen to believe it is ethically and morally wrong in the failure to treat others as we would be treated ourselves. It's a failure. But here I'm making the case pragmatically why it's a very good idea not to lose your temper for the host of reasons we've just explored.

• 16:09Ryan Holiday?

  Well, the way I think about it, to go back to sports, is like, what do you try to do when you're playing against someone? You try to make them angry because you know it may... That's the whole purpose of trash talking, is that you know that when one is angry, they act irrationally or they act emotionally and it comes back to haunt them. So why would you inflict that upon yourself?

• 16:33Speaker 01

  Indeed. In this regard, I'm a tennis player. I played intercollegiate tennis for Navy, squash also. So I know racket sports pretty well. And it's really a function in those sports... Of trying to break the concentration of your opponent. And in that case, the way to do it is to be very, very steady and return ball after ball after ball. This is the Michael Chang, late 20th century Asian American tennis player, who I like because he's like my size, like one foot six inches tall. And that almost zen-like ability to retrieve the ball can ultimately break an opponent quite quickly.

• 17:17Ryan Holiday?

  No, in my, in my book, The Obstacle is the Way, I talk about Arthur Ashe. You know, his, the amount of pressure, the amount of horrible things he had to endure, but he sort of channels that out on the court. And then you compare that to the, you know, the, the tantrums of John McEnroe or something. And you go, who, one, who's the greater man? But two, what's the more sustainable strategy?

• 17:39Speaker 01

  Yeah, as you probably discovered reading about Arthur Ashe, one of his quotes, and I, I really commend his autobiography, which is a gorgeously written book. And in the book, he says, I'll paraphrase it here, in a match, you're not really playing an opponent. You're always playing yourself. And I, I think that's, I think that's so true. He also said, by the way, to this whole question we wrestle with today, and you alluded to it a moment ago, of, of social injustice and being black in America. He said, and I think this is really true, being black in America is like having a second full-time job. In other words, you've got to be up on the issues.

• 18:24Speaker 01

  You've got to have thought through all your positions. You have to know the history. You're constantly in the middle of a conversation, whether you want to be or not. And, and Ashe, I thought, carried himself with such immense dignity and kindness and was really an exemplar in, in a lot of different dimensions, including parenting. The, the end of the book, the autobiography, he knew he was dying of AIDS, which he had contracted due to a blood transfusion, of all things. He'd always had heart problems, which he had to overcome. That's why he had a transfusion. He had a beautiful little daughter named Camera. His wife was a photographer.

• 19:06Speaker 01

  And he wrote a letter to Camera, knowing that he wouldn't be around to parent her. And I

• 19:14Speaker 01

  In the course of raising two wonderful daughters who are millennials, you know, kind of late 20, early 30, one of each, I would often pull that letter out from Arthur Ashe. The title of the autobiography is Days of Grace, and I cannot commend it more highly to people.

• 19:33Ryan Holiday?

  What strikes you most about the letter? I'm a huge Arthur Ashe fan, but I haven't read this.

• 19:38Speaker 01

  First, that he would write it in such a kind of practical way. And Ashe was a practical kind of thinker. He wasn't a hugely emotional person. And the letter is full of very specific admonitions to camera about dating, about what would happen to her growing up as an African American, about her mother. And it's very moving in that it's very practical. It's very moving in that it also hits some grace notes

• 20:20Speaker 01

  that will pluck at your heartstrings, as any such letter will do. And then, thirdly, simply knowing it's from Arthur Ashe, and as you alluded to, what he overcame in his life, kind of the male version of Althea Gibson, the great first African American who went through all this. Ashe sailed in her wake, truly, but was always very cognizant of it. And he manages to capture all this in just a lovely letter.

• 20:54Ryan Holiday?

  He has a great expression that he tries to play, physically loose but mentally tight, which I think is a great way to do any sort of high-performance, elite activity.

• 21:06Speaker 01

  Yeah, I think that's right. I hadn't heard that quote. It's a good one.

• 21:10Ryan Holiday?

  So you have a sort of a titillating exchange in your book about an evening you spent in a hot tub with James Stockdale, which is not a phrase I ever thought I would hear myself saying, but I would love to hear that story because it must have been a surreal experience.

• 21:28Speaker 01

  Well, first of all, I know the Stock knew the Stockdales through the US Naval Institute and always was fortunate to be relatively close to them. The US Naval Institute is the professional organization of the sea service. It's kind of like the American Medical Association. And I spent a fair amount of time getting to know the Stockdales around the time their book came out, In Love in War. And we were at a US Naval Institute event and, you know, ended up around the pool and really talking about life. And believe me, I was completely

• 22:10Speaker 01

  in the receive mode. I was perhaps a lieutenant commander. I was a very young officer in awe of Admiral Stockdale. And what really struck me about him are the things that always strike people about or struck people about James Stockdale, which is, to the title of this podcast, his knowledge of Greece and Greeks and Greek philosophy, and in particular, Stoicism, and the way that he was able to carry that with him as he was, in effect, parachuting into the Hanaway Hilton. And the easy way he carried his stardom, if you will, the kindness he showed to his wife, to my wife. He was an exemplar in so many different dimensions.

• 22:54Ryan Holiday?

  Yeah, it's interesting for me, you know, writing about this philosophy and these philosophers who lived so long ago. You know, you read about a Marcus Aurelius or an Epictetus or Seneca, and there's this, it's impressive and it's, it's, it's almost unbelievable. You go, oh, this happened such a long time ago. They don't make human beings like that anymore. You know, even in your book, you know, you're talking about a Francis Drake or a Themistocles, you know, that it- This feels like something that can't happen anymore. And to have, I think what's so surreal about his story is that it, I mean, it was not that

• 23:32Ryan Holiday?

  long ago, you know, and it was, it was as epic and he was fulfilling these ideals and these ideas on par with, with these sort of great historical figures. It's, it's, it's strange to think about even.

• 23:48Speaker 01

  And yet, doesn't it tell us that the human spirit renews itself, generation after generation? And, you know, people talk a lot these days about the greatest generation, about these Americans who marched off to war in the Second World War. And they were a great generation and they are largely now passing from the scene. I'll tell you, I would not underestimate these millennials. And if you look at American history and you look at the cycles of character in American generations, about every fourth or fifth cycle is a so-called hero generation.

• 24:30Speaker 01

  And the last one was the greatest generation, the World War II generation. I mean, they did many great things. And then there were, you know, the baby boom is of course the massive one that I'm a part of. And there've been a couple others, but the one to watch, I think, are these millennials. And I have two daughters who are millennials. They're both married to two wonderful young men. Two of them are physi-, the two boys are physicians. One of my daughters is a nurse practitioner. The other one is a tech executive at Google. What do they have in common? What they have in common is they care about other people deeply. They are truly moved by these conversations in America today about inequality and racial

• 25:15Speaker 01

  injustice. They're hardworking. And of them, two of the four served or serve in the military, one of the boys and one of my daughters. And I know that generation through them, but also having led that generation into these so-called forever wars in Iraq and Afghanistan. I've spent a lot of time in the field, a lot of time on Navy ships at sea, a lot of time in hangar days, talking to these millennials. And they-

• 25:49Speaker 01

  They care about their country. They care about each other.

• 25:54Speaker 01

  I would bet 50 years from now, we'll be talking about the millennials as one of these hero generations. I hope so.

• 26:02Ryan Holiday?

  That is the interesting thing about Stockdale's story. I think, you know, the superficial glance is just the kind of the superhuman strength and the endurance and the determination that he exhibits. But what I think so fascinating, whether you're looking at his story, or Denton's story, or McCain's story, is that what was at the root of that sort of defiance and unbreakableness, it wasn't this sort of selfish, superhuman, like, you're not going to beat me. It was, I'm not going to let you beat me because these people are depending on me. You know, like, when Stockdale attempts to kill himself, he wasn't doing it because he didn't want

• 26:45Ryan Holiday?

  to be tortured and spill secrets. He did it because he thought it could end torture in the camp for everyone else. So there's this profound selflessness in their stories that I think kind of gets glossed over because Vietnam was such a complicated conflict.

• 27:05Speaker 01

  Indeed. A book that I often recommend to people who want to understand what it's like for people in combat is Gates of Fire.

• 27:16Ryan Holiday?

  Yes.

• 27:16Speaker 01

  by Even Pressfield. And you may recall, it's about the 300 Spartans who stand and delay the massive Persian army as it seeks to invade and conquer Greece. And there's much to admire about that book and much to learn from it. But there's a conversation in it about, by the Greeks, about why they stand in battle. And to boil it down quickly, the comment is simply that. In combat, the opposite of fear is not courage.

• 27:57Ryan Holiday?

  It's love.

• 27:59Speaker 01

  Is love. It is love, philo in Greek, for the men and women who stand on either side of you. And that is as true today as it is for the ancient Greeks or any other civilization two, three, four thousand years ago.

• 28:19Ryan Holiday?

  Got a quick message from one of our sponsors here and then we'll get right back to the show. Stay tuned.

• 28:26Ryan Holiday?

  No, I love Stephen and actually Stephen's been a mentor of mine since I started as a writer and I reread Gates of Fire at the beginning of the pandemic and I'm very glad I did. I think one of the things that's been so hard for me to wrap my head around the last 12 months, you know, totally agree with your points about the sort of millennial generation. Stephen wrote a great piece about, you know, the Spartan, the Spartan line, that the Spartan soldier carries their shield, not for their own protection, but to create the impenetrable line for the person next to you. You couldn't invent a better metaphor for that than masks during the middle of a pandemic or social distancing in the

• 29:10Ryan Holiday?

  middle of a pandemic, he was saying. And just how hard that's been for people to do. And how little it actually asks of us. I think, I think, I think that's been the hardest thing for me to watch and to struggle with. It's like, it's been hard to watch people who you care about not care about other people.

• 29:37Speaker 01

  I think that's right and I. Another book by Stephen you may have read is called The Afghan Campaign. And of course, it's not about our current war in Afghanistan or the British campaign. You know, Afghanistan is the graveyard of empires, as the saying goes. This is about Alexander the Great marching through Afghanistan, the first time someone in recorded history, anyway, really tries to conquer it. And many of these same themes are excellent there. He is quite a marvelous writer.

• 30:12Ryan Holiday?

  Yeah, it's fantastic. He, yeah, I love him so much. I was curious, too, this idea of selflessness. It's something I'm working on in my next book. I'm curious, you know, you talk about these sort of great admirals and generals of history. But then there's also the moment, you talk about disobeying orders. There's the great MacArthur line about you become famous for the orders you disobey. And I was thinking about, on the one hand, it strikes me that military culture is about creating people who follow the rules, who stick to the rules, who know what to do, know the protocol.

• 30:56Ryan Holiday?

  And yet, there's also these sort of great moments. There's one in the pandemic on the USS Theodore Roosevelt, where sometimes the commander has to, I don't want to say go rogue, but the commander has to be willing to violate protocol in service of a greater good.

• 31:14Speaker 01

  So I'm very familiar with this case. Captain Brett Crozier worked for me as a commander, was a targeteer, someone who was in charge of selecting targets in combat for me in the Libyan campaign. And so that's a very delicate job. It's where you, as the targeteer, are the one who goes to the commander and says, yes, we can hit this target safely without creating collateral damage. And it's because of the way we wage war, following the laws of war and with morals and ethics intact, you come as a commander to depend a lot on your targeteers. So I got to know Brett pretty well.

• 31:57Speaker 01

  Through that campaign, this is back in about exactly 10 years ago, and tracked his career along. He was absolutely certain Brett Crozier was going to be an admiral in the Navy. He took command of the Theodore Roosevelt in a blaze of glory, went off to sea, and then this pandemic occurs. And I know him and I know his qualities well. And what he did was sacrifice his career for the good of his sailors. And he could have chosen otherwise. He could have simply suffered through the situation, let the Navy stumble around trying to figure out what was going on. And in fairness, all this happened at the very beginning of the

• 32:38Speaker 01

  pandemic, before we knew, you know, what the conditions were. You know, this is the point of time in the pandemic where we're all wiping down our groceries, right? Right. Because we're certain that just touching the surface will give us COVID. Of course, now we know that's just not true. It effectively can't live on a surface. Sure. It's a breath-to-breath transmission. That wasn't known at the time. So he had hundreds of sailors constantly wiping down the carrier. He did everything he could imagine. The Navy could not give him a set of solutions. He knew a massive percentage of his crew was infected,

• 33:19Speaker 01

  and so he chose to make very public what happened. Now, here's where there's a footfall by Brett Crozier. He could have launched that red flare inside the boundaries of classification. He put it in an unclassified email. I think if I'd been on his shoulder as his good angel, I would have said, "Your email's perfect, Brett, but put it in a classified format." And if he had done that, I think he probably would have completed his command tour and gone on to be an admiral. But he felt that he had to go right now, that time was of the essence, that if he classified

• 34:02Speaker 01

  it, it would slow everything down, would allow the Navy to just, you know, kind of hold it inside a little bit longer. And so he launched a pretty significant red flare. Cost him his career. I'm still in pretty constant contact with Brett Crozier. In my next book,

• 34:21Speaker 01

  Is a nonfiction book called Nine Hard Choices. Because I'm fascinated by decisions, by how we decide things, the big things in our life, and what drives those big decisions. And like Sailing True North, which is about the lives of ten admirals, this is nine naval figures, different ones completely, who make very hard choices. The ninth one is Brett Crozier.

• 34:49Ryan Holiday?

  That's fascinating. Yeah, it's, it's, it's, I guess what we're really talking about here, too, is the distinction between physical courage and moral courage, and the willingness to risk something more intangible, one's reputation, one's job, one's social status. It's fascinating to me how often that's even scarier to people than, than the physical risks.

• 35:14Speaker 01

  Indeed, it is. And it's because we tend to think a reputation hangs on it in such real ways. And physical courage, you know, I think Abraham Lincoln got it about right. All men can stand adversity. If you would judge a man's character, give him a little bit of power. And I think that when you are dealing with a moral decision, you feel as though it, it will be part of the judgment that's rendered on you by everybody. In other words, physical courage, there's only a very small number of people who have to deal with the challenges of physical courage, right? Very few.

• 35:59Speaker 01

  But everybody deals with moral questions all the time. So I think, for me, I would, I want to get them both right.

• 36:08Ryan Holiday?

  Sure.

• 36:09Speaker 01

  But I really don't want to get that moral courage question wrong.

• 36:15Ryan Holiday?

  Yeah, and I'm, uh, let's talk about Theodore Roosevelt because you've got the bus behind you and we're talking about the USS Theodore Roosevelt. I'm fascinated with philosophy, but why I love the Stoics is that there's this great expression from Junius Rusticus, one of the Stoics, he talks about the pen and ink philosophers, that he doesn't want to be a pen and ink philosopher, wants to be a philosopher doer. And it strikes me that that's, that's, that's the through line of Theodore Roosevelt's life. He wants to be the man in the arena. He's brilliant. He's an academic. He could have been a historian. He could have been a philanthropist, but he decides instead to pursue not just the strenuous life, but really the active life.

• 36:55Speaker 01

  Absolutely. And by the way, I always say about Roosevelt surprises some people. I think we'll find he's the only person in American history to win both a Medal of Honor and Combat and a Nobel Peace Prize. Those two don't often go together. And I think to your point about the breadth of Theodore Roosevelt, the other great quote about him, and he was guilty of this, is that Teddy Roosevelt wanted to be the bride at every wedding and the corpse at every funeral. He had to be at the center of everything. That's kind of the man in the arena piece of this thing. But boy, did he tackle life

• 37:36Speaker 01

  full on. And he died very young. And I think because of the death of his first wife and his baby daughter, while he's a very young man, he always had that sense of time's winged chariot at his back. And he did die very young. I think at 60. And having been out of the presidency for 10 years, by the way, and really just packed his life. And that's what I admire about him, is that he hit life head on. He was unafraid to make mistakes. I think another quote, I think it's by Roosevelt, is when you're faced with a hard decision...

• 38:20Speaker 01

  The best thing you can do is make the right choice. The second best thing you can do is make the wrong choice. And the worst thing you can do is just not to make a choice, which unfortunately is what a lot of people do. He was willing to make choices again to be the man in the arena. There's a lot to admire about that philosophy.

• 38:39Ryan Holiday?

  Well, I wonder how it works for you because, I mean, you're a historian, now you're a novelist. You clearly love big ideas. You work in business. You've done all these things. Did you, is that, are those pursuits or ideas that you wanted to do after your time in the Navy? Or was the idea that the time in the Navy would influence those things? Or how do you sort of balance the cerebral and the physical sort of domains or careers that you've had?

• 39:10Speaker 01

  I think everybody's life, when you've had a relatively long life, I'm in my 60s, is like a series of books on a shelf. And you get to kind of decide what the book's going to be. What you don't know is what's going to be inside each book. I think that I always felt I would want to do three or four books. I knew I wanted a career in the military because I grew up in the military. My father was a career military officer. I loved the ethos of the military. I liked wearing a uniform. I liked serving the country. I liked mentoring young people. I came to love the sea. I came to love being a mariner. My father was in the Marine Corps.

• 39:52Speaker 01

  He was kind of a land grunt, fought in Vietnam, Korea. I was like, we alluded to him earlier. I went to the Naval Academy thinking, oh, I'm going to be a Marine, just like my dad. They put me on a ship after my freshman year, your plebe year at the Naval Academy. And I walked up on the bridge of that ship as it got underway from San Diego Harbor. And I was like Paul on the road to Damascus. I mean, the scales dropped before my eyes and I wanted to be a mariner. So another book for me is not just that military career, but a book of being a sailor is an important one for me. Thirdly, I always knew I wanted to study and learn the international world.

• 40:37Speaker 01

  I lived in Greece as a child, went to a French speaking school. I've always had an international set of connections. And so for me, logically, I knew a part of the book for me would be the international world, and that's what led me to the PhD at the Fletcher School. And then, fourth, I'll stop in a minute. Fourth, I always wanted to be a teacher. I think being a teacher is one of the great things you can be in life. And certainly, there are teachers who are in classrooms, and there are teachers like my father, who taught everyone he was ever around, maybe not in a formal sense, but he was always looking to instruct, you know, that idea of the teachable moment.

• 41:20Speaker 01

  So the idea, when I got out of the Navy and was casting about for what do I want to do, I went to one of my life mentors, Secretary of Defense Bob Gates, and I said, "Sir, what do you think I ought to do next?" And at that point, everyone had a plan for Stavridis, and the plans ranged from go to the defense industry, to go to Wall Street, to run for office. You know, there were a lot of plans for Stavridis. Gates was the only mentor who actually asked me a question before launching into his advice. And Gates said, "Well, what kept you in the Navy for 37 years? Maybe that would give you a clue about what you want to do next." And I kind of reflected on that, and I realized that I liked going to sea, I liked being

• 42:05Speaker 01

  a mariner, I liked wearing snappy uniforms, I liked serving my country, I liked traveling the world. But the thing I loved was mentoring young people, helping guide their journey. And I said that to Secretary Gates, and he said, Education, you ought to become an educator. And we forget this about Bob Gates. Everyone can tell you he was Secretary of Defense. Most people can tell you he led the Central Intelligence Agency. He was a career officer there. What did he do in the middle between those two jobs? He was dean of the Bush School of Government and then became president of Texas A&M. He spent 10, 11 years in higher education. He helped me get the job as dean of the Fletcher School. That's kind of that fourth book.

• 42:50Speaker 01

  And then fifth and finally, I've always enjoyed international business and finance. It's what I studied as part of my graduate education on the international side. So now I'm doing private equity in the Carlyle Group, very internationally oriented. So each of those books was, I would say I could have told you when I was 20, what those books would look like. I couldn't tell you what the pages inside of each of them would be.

• 43:20Ryan Holiday?

  Got a quick message from one of our sponsors here and then we'll get right back to the show. Stay tuned. When you mentor a young person and you, let's say you walk through this philosophy of books on the shelf, do you advise that it's one book at a time or can they be in the middle of working on two books at the same time? I'm just trying to think about my own career. It's, I've done, I've tried both types, but I'm just wondering what you think is the most effective?

• 43:50Speaker 01

  I think the best thing you can do is have a book that allows you to have a wide variety of different kinds of pages inside it. And that's what the Navy was for me because one minute I'd be the captain of a destroyer leading 400 men and women into combat in the Arabian Gulf. A year later, I'd be in the Pentagon doing long range planning, focused on budgetary systems for the United States Navy. Two years after that, I'd be the chief of staff to the Secretary of Defense managing high level acquisition and intelligence for Secretary Don Rumsfeld. So having a book, let's call your book right now.

• 44:33Speaker 01

  That of commentary and communicating ideas. But within that book, you've got podcasts, you've got articles you're writing, you've got books you're writing, you've got speaking you're doing. There are many ways those pages can be oriented at this stage for you. But I'm intrigued by your question, and I think it is possible in some professions to have a completely different book going on off to the side. That hasn't been my experience, but maybe it's been yours.

• 45:08Ryan Holiday?

  It has a little bit. I mean, what I what I tell people who talk about wanting to be a writer is that you have your previous book has to have been really interesting. And now the metaphor is getting twisted. But the point is, like, the best advice I got when I was wanting to be a writer, they said, you know, writers live interesting lives. Basically, that you have to go do stuff to then, you know, drive the the point of view in the book. Just like, I'm sure you could have written this book as a as an academic professor, but it wouldn't have been as good without the actual experiences that you had that shaped your understanding of these people.

• 45:46Speaker 01

  Yeah, I completely agree with that. My co-author on this novel, 2034, and we should probably wrap up with

• 45:54Ryan Holiday?

  Yes.

• 45:55Speaker 01

  question or two on that, is a guy named Elliot Ackerman, who's a millennial-ish. I think he's in his very late 30s, might have turned 40. But he's a combat marine officer, Afghanistan, Iraq, and then got into the CIA, was a CIA officer, recipient of the Silver Star, the Bronze Star, Purple Heart, then gets out of the military, becomes a White House Fellow, gets involved in political theory, working on third-party ideas for the United States, and then becomes a writer, you know, kind of his third book, if you will. And he's led a very interesting life, as you can tell by what I just told you.

• 46:36Speaker 01

  And he continues to be effectively a war correspondent while he writes this novel with me. But his other novels are very atmospheric, very different than 2034. So, yeah, I think you can have a couple of different books, if you will, in your life going on at the same time.

• 46:55Ryan Holiday?

  No, I found, I thought Green on Blue was an incredible novel, a haunting, dark, dark novel, but, but, but a great one. And as you set out to write this book, what is it that you thought fiction would allow you to accomplish that, you know, nonfiction or, or, or your other work wouldn't, wouldn't allow you to do?

• 47:15Speaker 01

  Yeah, this is a great question because I could have written a book about geopolitics in the year 2034 as a kind of an academic treatise and laid out many of the same ideas. But here's the news flash, many, many, many more people are going to read 2034 than would have read that other book I just described.

• 47:37Ryan Holiday?

  Sure.

• 47:38Speaker 01

  Why? Because it's a story, because it's a character-driven story. This book is not techno-thriller. This is not Tom Clancy. If that's what you're looking for, go back to Tom Clancy. This is about the human character facing the greatest of challenges. The backdrop to it happens to be a war between the United States and China. And it is constructed as a cautionary tale, much like Cold War literature was. So think Doctor Strangelove, the Bedford Incident, fail-safe. Many, many novels, I think, helped us avoid stumbling into a hot war during the heights of the Cold War because we could imagine how terrible it would be.

• 48:23Speaker 01

  So, character-driven, lots of imagination in it and a wider readership. Cautionary tale. I hope it never happens. That's the idea of 2034.

• 48:36Ryan Holiday?

  That's something I think people miss about philosophy because it seems so distant. But when you read any of the ancient philosophers, the one thing, it doesn't matter what school you're reading, what they all have in common is how regularly and consistently they draw on theater and literature and poetry, because these were the ways that they communicated these ideas, and there was a familiarity with them. So I think sometimes people who are really smart get sort of trapped in a bubble of their own smartness where they don't open themselves up to fiction, or story, or literature, or television. And it's a great way to learn.

• 49:19Speaker 01

  Hundred percent agree with that. And my next book after this is called The Sailor's Bookshelf: Fifty Books to Know the Sea. And it is half fiction, half nonfiction, and it runs the range of ship handling and navigation, and oceanography, and Rules of the Road, to the environment, Jacques Cousteau, The Silent World. But on the fiction side, it's full of books, character. And I want to surface one for our conversation as we wrap things up. And I will, I'll start by saying, if you ask anybody, what's your favorite book?

• 50:01Speaker 01

  And it's a novel, they're going to tell you the name of a novel because a character

• 50:07Ryan Holiday?

  Sure.

• 50:08Speaker 01

  captured them. And the book in this regard that I always use as an example, it's a book about a stoic, a book about a stoic.

• 50:17Ryan Holiday?

  Okay.

• 50:18Speaker 01

  The Old Man and the Sea.

• 50:20Ryan Holiday?

  Of course.

• 50:21Speaker 01

  It's Hemingway. Santiago is, you can drop a plumb line from the Stoics to Santiago. And And his resilience and his his effort in what he knows is a doomed cause at the end of the day. It's a gorgeous book. And it I read it at least once a year and you can you know, you can read it in a sitting. In fact, the true first edition of The Old Man in the Sea is not a book. The true first edition is Life Magazine. It was published in its entirety in Life Magazine. 2034 was the first half of it was the February issue

• 51:00Speaker 01

  of Wired Magazine. So things have moved on. But the point is, Santiago and his character have stayed with me my whole life. And I think is a good example of this idea of character is what drives great literature.

• 51:17Ryan Holiday?

  Well, what does Hemingway say? A man can be destroyed but not defeated. I think that's the essence of Stoicism and Stockdale certainly.

• 51:26Speaker 01

  That's the that is that line comes from The Old Man in the Sea. Santiago has that line. And it's just a beautiful book. And when Santiago finally stumbles back in after his tragic, but beautiful adventure on the sea, that next generation comes along and picks him up and helps him. There's another piece of this, which is what we owe to the generation that came before us, back to those millennials.

• 51:57Ryan Holiday?

  One other short piece of sea fiction that I'm sure you've read that I'd love to hear your thoughts on. It strikes me as being relevant these days, but A Man Without a Country.

• 52:08Speaker 01

  Oh, sure. Yeah, this is another marvelous book about someone who damns the United States of America. And it's a metaphorical kind of book, but he's literally sent to sea for the rest of his life without being allowed to touch land again in the United States. By the end of the book, he has quite an epiphany in that regard. And it's a book about About our country and about patriotism and about what we hold dear. And back to where we started this conversation almost an hour ago, can people change? And the man without a country changes in the course of the book. That's another thing I like about it.

• 52:53Ryan Holiday?

  Yeah, he realizes what he took for granted. And there's a reason that was written at the height of the Civil War.

• 53:00Speaker 01

  Correct.

• 53:01Ryan Holiday?

  Admiral, thank you so much. This is a true honor. I love the book. I'm so excited about the new one. And I want to talk about this Hard Choices book. So as soon as it comes out, you let me know.

• 53:10Speaker 01

  Will do. Thanks so much. Great chat.

• 53:13Ryan Holiday?

  Thank you, sir. Appreciate it.

• 53:15Speaker 01

  Yep.

• 53:17Ryan Holiday?

  Thank you for listening to the Daily Stoic Podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple of years we've been doing it. It's an honor. Please, spread the word. Tell people about it. And this isn't to sell anything. I just wanted to say, thank you.