Lt. General H.R. McMaster on Strategic Empathy and Seneca’s Contradiction

On today’s episode, Ryan talks to Lt. General H. R. McMaster about why leaders must study history and philosophy, his book Dereliction of Duty about the controversial Vietnam war, Seneca’s complicated service for the emperor Nero, and more. H. R. McMaster is a retired United States Army Lieutenant General who served as the 26th United States National Security Advisor. He is known for his roles in the Gulf War, Operation Enduring Freedom, and Operation Iraqi Freedom. His book, Battlegrounds: The Fight to Defend the Free World, was released in September 2020 and is an overview of the most critical foreign policy and national security challenges that face the United States in the modern age. This episode is brought to you by Beekeeper’s Naturals, the company that’s reinventing your medicine with clean, effective products that actually work. Beekeepers Naturals has great products like Propolis Spray and B. LXR. As a listener of the Daily Stoic Podcast you can receive 15% off your first order. Just go to beekeepersnaturals.com/STOIC or use code STOIC at checkout to claim this deal. 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. Policygenius helps you compare top insurers in one place, and it lets you save 50% or more on life insurance. Just go to policygenius.com to get started. Policygenius: when it comes to insurance, it’s nice to get it right. 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.***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 H. R. McMaster:Twitter: https://twitter.com/LTGHRMcMaster Instagram: https://www.instagram.com/ltghrmcmaster 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.

• 0:02Ryan Holiday?

  Welcome to the weekend edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something that can help you live up to those four Stoic virtues of courage, justice, wisdom, and temperance. And here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We reflect. We prepare. We think deeply about the challenging issues of our time. And we work through this philosophy in a way that's more possible here when we're not rushing to work or to get the kids to school, when we have the time to think, to go for a walk,

• 0:44Ryan Holiday?

  to sit with our journals, and to prepare for what the future will bring.

• 0:53Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. Marcus Aurelius talks derisively of this idea of pen and ink philosophers, people who just talk about or study philosophy in the abstract. Most of the Stoics were doers. They were politicians, or generals, or advisors to kings, or world leaders. So my guest today is a man of that mold, a historian, but also a three-star general in the United States Army, a veteran of the Gulf War, Afghanistan, Iraq, a counterinsurgency expert, and ultimately, the national security advisor to the President of the United States. I'm talking about the one and only General H.R. McMaster. He served the Trump administration,

• 1:37Ryan Holiday?

  but I promise you, this is not a particularly political episode. We actually nerd out about philosophy and history, talk about Thucydides, we talk about Vietnam. General McMaster is the author of a fantastic book called Dereliction of Duty, which is about the flaws and the failures of the Vietnam War, the failure of advisors to speak truth to power, to get truth up to the presidency, and some of the ego and the delusions that led to the catastrophic failure and moral atrocity that was the Vietnam War, and the lessons he learned from that. And the experience he tried to bring with that when he was advising the most powerful man in the world, the president of the United States of America. He's the author of two books,

• 2:19Ryan Holiday?

  as I said, Dereliction of Duty, and most recently Battlegrounds: The Fight to Defend the Free World. We talk about this great concept in his new book called Strategic Empathy, which I think is a very stoic concept. And as it happens, he and I recorded this podcast over Zoom, which he was recently named to the board of directors of. So there's a lot of great insights here about history, but also we conclude talking about Seneca and Seneca's complicated service for the Emperor Nero. So this is one of my favorite episodes I've done in a while. I was really looking forward to this conversation and I can't wait for you to listen to my interview with General H R McMaster. And please check out his book, Dereliction of Duty, and his new one, Battlegrounds: The Fight to Defend the Free World.

• 3:05Ryan Holiday?

  Well, I was wondering, are you comfortable telling the story of how you ended up hearing about the obstacles, the way?

• 3:13Speaker 01

  Yeah, no, I'm fine with doing that. I'm fine with doing that. Yeah.

• 3:15Ryan Holiday?

  I'd love to. I'd love to hear it.

• 3:17Speaker 01

  I've got my copies, man. I got all three of your books right there, man.

• 3:20Ryan Holiday?

  Oh, no way.

• 3:23Speaker 01

  But I'll tell you, I love your books, really, honestly. I mean, I think they're great. I mean, I love like kind of the short chapters, man, you know, they're great bedside books and,

• 3:33Speaker 01

  and you know, it's really, it's just a strong, it's a great message for these days. You know, my daughter is, she's probably 33 now, but she calls her generation to start my orange generation. You know, hey, will you start my orange for me?

• 3:49Ryan Holiday?

  Oh, you mean start, start peeling it?

• 3:51Speaker 01

  Yeah, start peeling it.

• 3:57Ryan Holiday?

  No, that's, that's, well, I mean, look, the pandemic has been that it's like suddenly, you know, I used to eat my lunch at a restaurant every day and now I'm packing my lunch for the first time and making my own lunch for basically the first time in my adult life. It is, it is sort of forcing some self reliance, which, which will hopefully counteract some of the, the millennial start my orange impulses.

• 4:20Speaker 01

  Exactly, exactly.

• 4:22Ryan Holiday?

  So how did you end up first hearing about The Obstacle is the Way? Someone gave it to you, right?

• 4:27Speaker 01

  Yeah, so Sheikh Taknoon, who's a friend of mine, and we worked together on a number of initiatives in the Middle East and beyond. He's an author himself. He's very intellectually curious. And he said, hey, I just read this great book called The Obstacle is the Way, and I'm going to bring it to you next time. And he did. He brought it to me next time. And, you know, he had it marked for me on the pages that he thought were most relevant to the problem sets that we're working on. And so that's how I became familiar with your work. And I really enjoyed it. And, you know, as well as The Eagle is the Enemy, and now The Lives of the Stoics. You know, so I'm a big fan.

• 5:05Ryan Holiday?

  It's so incredible to me, because I also have had the unique opportunity of meeting him. I met him through Robert Greene, who wrote The Forty Eight Laws of Power. He's obviously a huge reader, and so he sort of reaches out to authors, I guess. But it was a surreal experience for me to go to Abu Dhabi and meet him, because there was something, you know, so they drove me in, I went to his palace, and it was all very modern. And this was this sort of Stoic thing came to me. It was all very modern. You know, it's this beautiful house. He has these TVs everywhere and cutting-edge technology. You know, there's nice cars parked out front. Yeah, I also felt something very timeless, where it's like you're literally meeting

• 5:48Ryan Holiday?

  a member of a royal family, and he's just soliciting sort of artists and intellectuals the way that a prince might have done 500 years ago or 1,000 years ago. And that must have been a feeling you've got as you traveled around the world, meeting these sort of heads of state. On the one hand, we're in the 21st century. On the other hand, very little has changed.

• 6:12Speaker 01

  I think that's right, you know, and in these countries, the power structures are quite different, but I think it's great that, you know, that someone who's in that position of influence is intellectually curious, right? I mean, the danger is when do you have a despot, right, who thinks, hey, I know everything already, right? And I know what's good for my people and is just really determined to keep himself in power. So I think that UAE has been kind of a force for good in the region, in large measure, because the leadership there, Sheikh Taknun, but also Mohammed bin Zayed is, you know, they're very engaged, they're always talking to others and listening to others.

• 6:53Ryan Holiday?

  Yeah, it's interesting. When I was writing Lives of the Stoics, I was looking at some of the early Greek Stoics, and I was, it was interesting, their relationship with these sort of kings and princes that they were advising, there was their, the idea of like, oh yeah, a leader has to be informed, and a leader has to be intellectually curious, is again, this thing that that people have been wrestling with for 2,000 years or more, and how unique, I mean, Marcus really is being one of the only sort of philosopher kings that ever existed, just, you would think that, you know, being powerful would go hand in hand with being intellectually curious, but it's probably the exception rather than the rule.

• 7:35Speaker 01

  Yeah, I think that's right. I think a lot of people who get into positions of power, you know, do so in a way that that demands self-promotion, right, that demands at least portraying themselves as extraordinarily knowledgeable, right, but it's really important that a leader be intellectually curious and be humble, right, to know that, you know, nobody's omniscient, and when you're dealing with certainly complex challenges, and also when you're trying to take advantage of opportunities, that you need a kind of interdisciplinary approach, you need to bring people together to help understand the complex problems and what the possibilities are.

• 8:18Ryan Holiday?

  Yeah, there's a, there's a great quote from Epictetus where he goes, "It's impossible to learn that which you think you already know." And, and as I've talked to sort of CEOs and leaders and politicians over the years, I've sort of set a version of this, which is if you think you know everything, in a sense, if you think you know everything there is to know, in a sense, you're right, because it becomes impossible for you to learn anything else. And so it's kind of this self fulfilling prophecy where if, if you think there's stuff left for you to learn, you're also right and you can continue to grow and learn. And if you think you know everything, which I think a lot of these sort of intuitive, by the gut leaders sort of go, almost probably come out of the womb thinking, that's also a self fulfilling prophecy because they, they're not open to learning

• 9:03Ryan Holiday?

  or, or being proven wrong in any way.

• 9:05Speaker 01

  Absolutely. I mean, this is why I think the study of history is so important, right? Because I think the study of history is in, in many ways, an exercise in humility. Because you, you recognize that nobody has everything figured out, right? And you, you understand better the complex causality of, of events, the, you know, the, the human aspect of, of problems and, and life experiences that, that defy, you know, any kind of predictive ability, right? So I, I, that's why, you know, no surprise that a historian would advocate for the study of history.

• 9:37Ryan Holiday?

  Of course.

• 9:38Speaker 01

  But I think, I think the study of philosophy and the study of history, both are immensely important for leaders.

• 9:43Ryan Holiday?

  Yeah, I was thinking about that quote from, from your friend and colleague, General Mattis. It's in, it's in Call Sign Chaos. He says, "It's not just that you have to read." He's like, "If you haven't read hundreds of books about your domain of, of battle or, or, or industry or specialty," he says, "you're functionally illiterate." And I, what I liked about that is it's sort of raising the bar. It's not like, "Oh, I read one book or I scanned a few reports about something." It has to be this deep sort of immersive experience in something to, I'm, I'm sure, you know, your sort of lifelong study of the, of war, but specifically the, the Vietnam War, you're, you're probably just, you're, you're not only still unearthing things about it,

• 10:27Ryan Holiday?

  but, but your understanding of it is probably still relatively early. Like we're, as you, as you deep dive in these subjects, you realize that you're really only on a shoreline of kind of a vast ocean of, of potential understanding of this topic.

• 10:42Speaker 01

  Right. And what history can do is it can help you ask the right questions. And I think it can help you think in ways that allow you to employ historical analogies. But I think you have to do that as well with a degree of caution and humility, because you know, no situation is exactly the same. But I think you can at least avoid making some of the same mistakes. And I read about this in Battlegrounds about how I took with me, you know, into the White House, a determination to at least make different mistakes than those that I had written about during the during the period in which Vietnam became an American war.

• 11:19Ryan Holiday?

  Yeah, Bismarck says, you know, any fool can learn by experience. Let's learn from the experiences of others. I think if you're not sort of starting at least where everyone else left off, what you're doing is making unnecessary mistakes for the second time.

• 11:34Speaker 01

  Right, absolutely. Exactly.

• 11:37Ryan Holiday?

  You seem like a pragmatic reader, though. I saw a quote from you in an interview, and I think you were cribbing a professor of yours, where you said, a historian doesn't read book, they, you said, historians don't read books, they use books. Walk me through how you think about books in that way.

• 11:53Speaker 01

  Yeah. Well, I think that really gets to the point that I was going to make when you mentioned the General Mattis quotation. It's not enough just to read books, you have to read books purposefully. And I think if you're reading books purposefully, what you're trying to do is to to kind of solve a problem or to deepen your understanding of a particular issue. And then when you engage with the book, and then you can place that book in the context of other books that are related to that subject, that's when I think you begin to develop knowledge, you know, the knowledge that is necessary to make wise decisions and knowledge is necessary to consult with others and to do so in a way in which you ask the right questions, right? And so I think reading purposefully is immensely important. And I mean, some books are more conducive to this than others.

• 12:37Speaker 01

  I mean, if I'm reading a book on a historical topic or a contemporary challenge to international security. I typically try to break the book, right? I read the introduction, I read the conclusion, I read the first and last paragraphs of each chapter and then, and then if a chapter really interests me, then I dive into it, you know, and I read the whole thing. Now, of course, you know, when you're reading Tolstoy, you read it, you read it from front to back, you know, skip around, but, but, but I think, I think reading purposefully is, is key and I think that's an important skill. I remember when I was, when I was in, I was taking a staff course on my way to graduate school and I went to the, the library at Fort Leavenworth, Kansas, and I signed out these VHS tapes for a speed reading course hosted by Dick Cabot.

• 13:24Speaker 01

  I'll say it's the best investment of time I ever made, you know, because of course, I mean, a graduate student in history, you're doing a heck of a lot of reading.

• 13:30Ryan Holiday?

  Sure.

• 13:30Speaker 01

  And if you, and if you can read purposefully and efficiently, I think that helps.

• 13:35Ryan Holiday?

  I, I find this particularly true for like philosophy or if I'm trying to read some like Greek play or like, let's say someone, you know, hears that, you know, history of the Peloponnesian War might help you understand the, the, the jostling between the United States and China, you know, don't just go buy that book off the shelf and, and think you're going to read it if you've never read some work of ancient history before. I, what I like to do is I read the Wikipedia page first and then I read articles about it. You gotta, you gotta get the basics of, of what's happening first. So then you can really understand what's going on. And then I also think, and I'd be curious as a, as a, as a historian, how like when I read, I tend to skip over lots of dates and places. I don't worry about pronouncing names.

• 14:19Ryan Holiday?

  I just, I just want to get to the, the point. I want to get the message. I want to use it. I'm not, I'm not trying to impress anyone.

• 14:27Speaker 01

  Yeah. Hey, Ryan, this, this is why I really like your, your books. I mean, you make your, you make philosophy and Stoic philosophy relevant and, and accessible. And a lot of other authors do that, I think, well on other topics. Like you mentioned, the Peloponnesian Wars. Don Kagan's one volume of that is brilliant, or his essay on it in the book called On the Origins of War and Prospects for Peace, right? He's a, you know, he's an, he's an ancient historian who wrote a multi-volume history of the Peloponnesian War. But like, who's going to read that these days? Not that many people. But, but so I think looking around for books like that to provide the context. And, and you know, you know, I, we're talking about Don Hagenbottom, one of my advisors, you know, who said, you know,

• 15:08Speaker 01

  who said, HR historians don't read books, they use them. He also had a great line when I finished my written exams in history for the, for the doctorate, and he said, uh, he said, congratulations, you now know more history than you will ever know. And what he was basically saying is, hey, don't worry about the knowledge, right? The specific, you know, knowledge of facts and dates and so forth and personalities. But, but, but you know, really what a degree in history should do is just teach you how to think. And, and, and how to think in maybe the way that Sir Michael Howard, who was a great military historian, who just passed away last year, you know, he said that you should study history in width, depth, and context, right? In, in width,

• 15:51Speaker 01

  so you can see really the change and continuity, because I think history is largely about change and continuity. As the historian Carl Becker said, "Memory of past and anticipation of future should walk hand in hand in a happy way," right? And, and, and I think oftentimes we neglect continuities in our experience, the human experience. I think, I'm sure you see this with the applicability of Stoic philosophy to today. And we think that everything's new, right? Everything's, everything we encounter is a, is a novel sort of experience. And, and then he said to study in depth, in depth, so you understand the complex causality of events. And, and as he describes it, "The tidy outlines of history dissolve," right? And, and you see

• 16:35Speaker 01

  the real effect that, you know, that emotion. Has on history and the course of human events. And then, and then, and then, and then you said to study in context, to place whatever you're studying in a broader context of if you're studying war, right, the relationship between war and society and the specific form of government, the need to sustain popular will in a democracy, for example. So, so I think that the study of history teaches us more than anything else, how to think rather than what to think.

• 17:06Ryan Holiday?

  Got a quick message from one of our sponsors and then we'll get right back to the show. Stay tuned. Yeah, I was with that quote from your professor was saying you now know more than you'll ever know. I wonder if part of that, and I'd be curious if this is true in your experience, it's sort of, it's, you had this broad understanding of the sweep of history. So you kind of know where things are located. And then when specific things happen, then you can go, I need to go deep dive into this. For instance, when I was writing Stillness, I decided, oh, you know what might be like, I was trying to think of a leader, a moment where a leader had been particularly sort of still, but, but in a very sort of crisis, high moving situation.

• 17:48Ryan Holiday?

  And so I was like, you know what, I've read about the Cuban Missile Crisis before. Now I'm going to go do a deep dive in context of that to find out what I need to know. So do you find yourself referring back, doing deep dives in moments of?

• 18:03Speaker 01

  Absolutely. Yes, yes. And whenever I'm writing about something or thinking about something, I'm pulling like three or four different books down because I'll remember, I'll remember, I think, I think this vignettes in this book or this book really has, has a good framework, you know, for understanding this, this, this, this complex issue. And I noticed that, I noticed that in your writing too. I don't know if it's ego is the enemy or obstacles away. You could cover Ulysses Grant and use, use a couple of vignettes about, you know, him getting a photograph taken, I remember, and like, you know, the glass crashing around him. I thought about this because you're talking about Stillness. But then all these other examples in his life where he was, you know, he, he, he was sort

• 18:44Speaker 01

  of, I think, you know, a little bit fatalist, you know, and, and, and, and was sort of unflappable in, in very, very, you know, what others would regard as, as harrowing, desperate situations. So, and, you know, I, I love that approach to, you know, to leadership, right? I mean, I, you know, I don't know, I think you might write about Rommel, too. I used to teach, I taught a symposium on the North Africa campaign as part of a military history course I taught at West Point. And, and I think what distinguished him more than anything else is where others saw only difficulties, he saw possibilities, right? And, and with our regiment in Iraq, the 3rd Armored Cavalry Regiment in Iraq,

• 19:26Speaker 01

  in a very difficult area with a lot of violence, and, and it was a base for Al Qaeda in Iraq, we had a big sign in our command post, right? Where, you know, where are the opportunities and how do we exploit them? And that was the question to ask all the time. Because, you know, bad things happen in combat, Ryan. But, but what you want to try to do is, is to understand how what has just occurred can be turned to your advantage.

• 19:50Ryan Holiday?

  Yeah, speaking of Rommel, to go to the, the idea of like, you sort of know where stuff is located. He had that, that fingertip feel. I won't do the, the German word because I, I'm terrible at pronunciations, but-

• 20:02Speaker 01

  Finger spitting of fuel is what it is.

• 20:04Ryan Holiday?

  Yes, he, he kind of had that fingertip feel for how things were going to go. And I think the more you read, the more functionally literate you become, the more you have a fingertip feel for where the right quote or anecdote or, or piece of data or campaign to study to help you with whatever the, the obstacle you're currently experiencing is.

• 20:23Speaker 01

  Absolutely. And this can be very practical. I read about this in the conclusion of Battlegrounds, because I, I tell the story of when I was, when I was leaving to go to the White House quite unexpectedly, right? The president hired me on, you know, President's Day in, in 2017, after an interview in Mar-a-Lago.

• 20:40Speaker 01

  And I flew back on Air Force One. I didn't live in Washington, so they flew me on Osprey aircraft back to my house. I packed a bag and I went to work the next day, you know, on the west wing of the White House. Sure. But my future son-in-law was visiting us and I was pulling all these books down off my shelf to take with me. He goes, hey, what, shouldn't you be packing clothes instead of books? Like, why are you taking all these books with you? Right. And I said, well, whenever I take on a new job, I try to learn from the experiences of those, you know, who had that responsibility previously. Sure. And I told the story about, to my son-in-law, who was in the 75th Ranger Regiment at the time. I said, you know, before our unit deployed to Desert Shield and then Desert

• 21:21Speaker 01

  Storm, this is 30 years ago now, Ryan, I'm getting really old, man. I read about the North African campaigns and then really strangely, our executive officer, a guy named John Gifford, he's cleaning out the office of the executive officer, which is always a mess in any military unit. The executive officer has all this stuff, like, gets socked away, right? He finds this paper, like, crumpled up, like, in the back of the drawer, you know, and it's notes on combat actions in Tunisia and North Africa by Major General Harmon, Ernest Harmon. And it was like a Rosetta Stone for armored desert combat, you know, and it was all the lessons that he had learned in command of the 2nd Armored Division. And, you know, technology had changed and so forth. The basics had changed.

• 22:06Speaker 01

  Right. And there were these just, there were these insights that seemed kind of simple, right? But he would say that armored battles in the desert are won by the side that shoots first, okay, that gets the first shot in. Sure. All right, that's kind of good. He said, a good, a good unit engaged in armored battle has about eight to 10 plays that they can, that they can execute immediately, you know, and together. He emphasized fire distribution and control, all sorts of other things. But, but, you know, there's one saying, if it takes a toothpick, use a baseball bat, you know, so, you know, bump up, in other words, to gain the initiative or an ascendancy of

• 22:50Speaker 01

  fire. The Rommel Papers read that way as well, very practical, you know, solutions, or Rommel's earlier book, Infantry Attacks. And so I think... You know, I think it's really important to study the past, not just because it makes you more knowledgeable in a general sense, as I mentioned, and the ability to ask the right questions, but sometimes it can really help you in a very practical sense, prepare a team to compete. And I think that applies, you know, in business as well as it does in the military.

• 23:19Ryan Holiday?

  Yeah, I would say sort of for whoever is listening, it doesn't matter what you're doing, what's just happened in your life. You've just gotten married, you've just lost someone you loved, you've just been drafted to play in the NBA, you've just been elected president, you've just made a million dollars, you've just lost a million dollars. Somebody has written a book about that exact thing, right? And probably someone who did it right has written a book about it, and somebody who did it wrong has written a book about it, and then a historian has written about it in context. And to not avail yourself of that knowledge, because you're going to figure it out on your own, is not just arrogant, but masochistic, in my opinion.

• 24:01Speaker 01

  Right, right. Absolutely. Absolutely. Yeah. I mean, what is the, what is the, gosh, I think you already mentioned the Bismarck quotation, you know, about learning from the past. And I think that it is arrogant, though. I mean, the people who say, hey, all I need to know, man, is what is my own experience. I mean, that's pretty darn arrogant, right? And the ego is the enemy, Ryan.

• 24:26Ryan Holiday?

  Seneca says, you know, to study philosophy is to annex all the ages into your own. And I think that's what we're doing, is we're trying to go, the wisest people who ever lived have experienced something like this before. What did they figure out? Maybe they got it wrong, but we should at least start with their basic understanding of the problem and, you know, speed things along if we can.

• 24:51Speaker 01

  Absolutely. And I think that if you don't have that historical knowledge, you're at a severe disadvantage, a significant disadvantage. And I think an example, I mean, the example that I read about in Battlegrounds is this idea of a revolution in military affairs in the 1990s. It was really based on the premise that, hey, really, really, really, this time, the next war will be fundamentally different from all those that have gone before it, right? It's going to be fast, cheap, efficient, way from standoff range. And the language associated was so hubristic, right? Everything was dominance, full spectrum dominance, dominant battlespace knowledge. And then these catchphrases like rapid decisive operations. That sounds great, doesn't it? I mean, if you're not for that, what are you for?

• 25:36Speaker 01

  Are you for ponderous indecisive operations, right? I mean, so it was really a setup. This orthodoxy in the 90s was a setup for the frustrations that we encountered in Iraq and Afghanistan. And it was all because we were biased in favor of change and not cognizant enough of the continuities, continuities in the nature of war.

• 25:56Ryan Holiday?

  Yeah, I read Lawrence Friedman's book, and it's called The Future of War. I don't know if you read it, but he wrote that great book, Strategy. And he was sort of looking at how at every generation, they thought things have fundamentally changed and are different, and how naive that assumption turns out to be every single time.

• 26:18Speaker 01

  Yeah, I used to call it the vampire fallacy. It's because you can't kill it. It just keeps coming back. And it's modern day, you know, the modern day manifestation of this vampire began with strategic bombing theory in the early 20th century. And it just appears in a new guise about every 10 years. You know, I don't know what generation of warfare we're up to now. I think it's fifth generation warfare, sixth generation, you know? And each one of these generations comes with a few new buzzwords, you know? But it's really the same argument. And the continuities that they neglect is kind of four fundamental continuities about war. War is an extension of politics, right? Okay, so you think that's kind of like the Geico commercial, right? Like, everybody knows that.

• 27:03Speaker 01

  But what it really, what that really means is, hey, you have to orient all of your efforts, military, diplomatic, economic, to achieve a sustainable political outcome, unless it's just a raid. War is human. And, Ron, you'll appreciate that, obviously, war is fought for the same Reasons Thucydides identified 25, 20 years ago, fear, honor, and interest. War is uncertain because of its fundamentally interactive nature. There's no such thing as linear progress in war. And then war is a contest of wills, right? As the philosopher of war, Karl von Clausewitz, said in the 19th century, you know, that winning in war means convincing your enemy that your enemy has been defeated.

• 27:48Speaker 01

  Right? And I think we have violated all of those continuities or neglected all of them in the recent wars that we've engaged in.

• 27:57Ryan Holiday?

  And for people who are listening who are not soldiers, I would argue that those points you just raised are as much true in life and in business and in sports, too. And that's why ordinary people should study the history of war and the history of politics and the, you know, these sort of grand campaigns of the past. Because as different as they are, what you're seeing is fundamentally human beings doing what human beings do. And there's lessons you can derive and apply to whatever it is that you're doing.

• 28:29Speaker 01

  Absolutely. This is, you know, Karl Becker, who's a great historian, who I already quoted earlier about the memory of past, anticipation of the future, walking hand in hand in a happy way. He gave a great speech in front of the American Historical Association in the 1930s. You know, and in it, the title was "Every Man a Historian." And of course, he would have said today, "Every man and woman is a certain historian." But what he was essentially saying is that history is important to everybody because it's really just the record of things said and done. And that record can inform, you know, our decisions and help us, help enrich our experiences.

• 29:10Ryan Holiday?

  So there's two things that you brought up. One, the idea of sort of convincing your enemy they lost. And then we talked briefly about the Cuban Missile Crisis. To me, of all the concepts that are applicable out of battlegrounds, the biggest one, the sort of one that I think obviously makes sense in a geopolitical sense, but make a lot of sense just as a human being going. Through the world, talk about this idea of strategic empathy, which is not just what do I want? What not just what do I want, but what does my enemy want? And how is my enemy going to think about what I'm doing? And how does that interplay with what they want? And to me, the Cuban Missile Crisis is this sort of apotheosis of that happening, where Kennedy was the first one, the first American president in quite some time,

• 29:54Ryan Holiday?

  that was able to to take the advice from his military advisers, think about it politically, and also just think about it as a human level. What is the guy across the ocean who also has his finger on the nuclear button? What is he thinking? And what's he thinking about what Kennedy's thinking? And that struck me as just strategic empathy at its highest and most life and death.

• 30:20Speaker 01

  It's an extremely important concept. It's a concept that has its roots in Sun Tzu's observation, right? That hey, you know, that if you know yourself, you know, you'll win half of the battles. If you know the enemy, you'll know half the battles. If you know neither, you'll lose everything, right?

• 30:36Ryan Holiday?

  Yes.

• 30:36Speaker 01

  So but but a historian named Zachary Shore wrote a great book called A Sense of the Enemy, in which he develops this idea of strategic empathy. It's essentially viewing these complex challenges that we're facing from the perspective of others. And in particular, as you mentioned, our rivals and adversaries and our enemies. And what he also argues for, and what I argue for in the book, is to also pay attention to the emotions and the aspirations and the ideology that drive and constrain the other. The problem with the lack of strategic empathy, or described as strategic narcissism, is it's self referential, first of all.

• 31:11Ryan Holiday?

  Sure.

• 31:11Speaker 01

  And it doesn't acknowledge the agency or the authorship over the future that the other has. And this is why I think we fall into some of these cognitive traps of confirmation bias and optimism bias and self delusion, really. And we see this playing out, I think, in Afghanistan, for example, today, right? Where we didn't like the enemy that actually we were engaged with there. So we conjured one up and made some assumptions about the enemy. And then and then and then are leaving Afghanistan a way that's empowering our enemy and disadvantaging really those who are trying to fight to preserve the freedoms that the Afghan people have enjoyed since the end of Taliban rule in 2001.

• 31:55Ryan Holiday?

  Yeah, I see this with artists and writers and entrepreneurs too, where if because these things sort of, I think, tend to select for a certain amount of ego, right? You're the person that says, "I should be a famous artist," or "I should be president," or "I should be a powerful general." There's a certain amount of ego that attracts you to these jobs. But that ego is so dangerous because your thing now depends on your understanding of the audience, of the enemy, of the media. You're having to be filtered through all these things. And so if you don't understand, if this is all about you, and you're living in this sort of reality distortion field, you're just never going to be successful,

• 32:36Ryan Holiday?

  no matter how brilliant, powerful, well armed you are, because fundamentally, it's not about you. The other person has a say in what happens too, whether that's Vietnam, or the buying public, or the stock market, or public opinion. They have a say in what happens, and you have to understand that.

• 32:53Speaker 01

  Right. And a person's ego makes them vulnerable as well to manipulation, right?

• 32:59Ryan Holiday?

  Yes.

• 32:59Speaker 01

  It's pretty easy to push the buttons to somebody who's an egotist, right? You can do that through your sycophancy, or by raising the prospect that the individual might seem weak, unless they do fill in the blank. The other way that I think ego makes people susceptible is the way that I've seen really the Pakistani army leadership manipulate American leaders for way too long, right? I mean, this is serial self-delusion. And I think what I've seen them do is they just convince each one of these leaders, "Hey, you will be the person. You will be the person who's going to convince me to change

• 33:43Speaker 01

  my behavior, right? And just work with me a little bit longer, right? Just continue to give us more aid. Be patient with us, because you're really the one that's going to fundamentally change the relationship." And I've seen a number of people fall for it. It's really, what it is, it's serial gullibility.

• 34:01Ryan Holiday?

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

• 34:07Ryan Holiday?

  Yeah, well, you sort of, you can't con an honest man, you know, the saying? And I think an egotistical person is complicit in fooling themselves because they want whatever it is that you're selling them to be true, even though fundamentally it's not.

• 34:22Speaker 01

  Absolutely. Yeah, exactly.

• 34:24Ryan Holiday?

  So when you, when you think about this strategic empathy, it's not, you're not saying like, oh, you never do, you never put yourself out there, you never try, you never exert your will. It's just, I think you're saying you have to understand the facts on the ground and you have to understand how these things relate to each other.

• 34:41Speaker 01

  That's right. That's right. And, and what strategic empathy does is it helps you understand the challenge you're up against better. It helps you compete more effectively. It allows you to challenge what are oftentimes implicit assumptions that underpin policies and strategies. And, and because they're implicit, and despite their flaws, they go unchallenged. Right? And so I, I think it's, for example, I think one of the, you know, one of the more stark examples is this assumption that, that China, having been welcomed into the international economic order, would, would play by the rules and, and as China prospered, it would liberalize its economy and liberalize its form of governance. Well, that completely neglected really what

• 35:22Speaker 01

  the, with the ideology of the Chinese Communist Party and the emotions and aspirations that drive the party leadership. So I think by viewing the competition that we're in with this authoritarian mercantilist model that, that the party is, the party is promoting, you know, that, that by viewing it from their perspective, you then are able to craft a much more effective policy and strategy.

• 35:46Ryan Holiday?

  Yeah. And just because something is good for the country as a whole, you have to think about how does this affect the individual decision makers who, who are currently in power and what the fantasy that you wish to be true is often at their expense. So it's, you know, I think this is a key point in the 48 Laws of Power. It's a key point in von Clausewitz, obviously Thucydides. You have to, to me, what the core of strategic empathy is, is understanding what the self-interest or the incentives acting on the person who's on the other side of you is.

• 36:18Speaker 01

  Absolutely. Yeah. A great example is the Kim family regime in North Korea, right? The only, the only hereditary communist dictatorship in the world, right? And, and, and so the, the two approaches that we've taken to, you know, to North Korea over time have been, you know, the sunshine policy, right? The sunshine policy that, the idea that an opening to, to North Korea, I mean, how could they be against that, right? I mean, they've got a, you know, the people are destitute, their economy is failing, you know, opening up will, you know, will, you know, will enrich the, you know, the, the, the people. But of course, Kim sees this as a disaster, right? Because it's a gulag state.

• 36:59Speaker 01

  It's a state in which he's, he tries to insulate the, the North Korean people from reality and his career is, and subjected them to, to systematic brainwashing, right? I mean, you know, the, the worst threat to him is that North Korean people would think on their own. And the other approach has been one of strategic patience, right? This, this idea that, hey, if you just wait long enough, right? I mean, that's the impossible state, it's going to collapse. Right. But, but this is, you know, this is again, I think, wishful thinking. I mean, the, you know, the Kim family regime does have a pretty tight grip on power based on the mechanisms is put in place to, to prevent any, any really organized, organized opposition to the regime. So it is, it is important to view, you know, to view competitions, complex problems and

• 37:44Speaker 01

  challenges as well as opportunities from the perspective of others. And then to, and then to maybe list assumptions. I think a good example of this is about three weeks ago, four weeks ago, whenever, just before the end of the Trump administration and in the, in the middle of this, you know, of this, this horrible, you know, spectacle, murderous spectacle and the, of the attack on the, on the, on the Capitol. So it didn't get much press, but the administration declassified one of the foundational documents to the Indo-Pacific strategy. And, and, and what that, what that strategy began with was a discussion of the assumptions that, on which previous policies were based that now were demonstrably false. And then, and then posited a, a set of, of, of alternative assumptions.

• 38:29Speaker 01

  And, and I think it's a great example of the application of strategic empathy to this competition with China. And I think this is an approach that it has tremendous bipartisan support as a result. And, and I think will carry on across multiple presidential administrations.

• 38:44Ryan Holiday?

  Well, that idea of questioning assumptions to me also is very philosophical, right? I think when I look at your work about Vietnam, what you really see is, you know, multiple presidential administrations refusing to question the obviously failing or flawed assumptions right in front of them. And if you want to look at it sort of a history on repeat, that's also the history of humanity is we make an assumption about something and instead of reexamining it continually in the light of new evidence, we stick to it, we cling to it despite all evidence to the contrary.

• 39:16Speaker 01

  Absolutely. And I think it's really important to try to put in a process to compensate for these flaws, right? And what I did as national security advisor, and I described this a little bit in the conclusion of the book, is, you know, armed with, as I mentioned earlier, the recognition of what went wrong in Vietnam, we put into place a different meeting for the principals committee of the National Security Council. This is the president's cabinet, you know, who are relevant to a particular problem or any issues of foreign policy or national security. And this framing session really just aimed to ensure that we understood, you know, the nature of this challenge to our security and our prosperity, and then to first understand

• 40:00Speaker 01

  it on its own terms, to identify what vital interests were at stake, to craft an overarching goal and more specific objectives, but importantly, to list out the assumptions on which we think a strategy or policy should, would be based. And then we listed what we saw were obstacles to progress and opportunities to exploit. And it just stopped there. We didn't talk about in the first part of this meeting, hey, what are we going to do about it?

• 40:28Ryan Holiday?

  Right.

• 40:29Speaker 01

  We talked about the framing, you know, this is what people call now design thinking, but you know, the framing of this challenge. And everybody had a chance to comment on it. And then we said, okay, what are your ideas then? If you agree now with this framing, modified based on the discussion, how do we integrate our efforts, the all elements of national power and efforts of like-minded partners to overcome the obstacles and take advantage of the opportunities? Then you get kind of a high-level discussion about how to integrate diplomatic efforts with military efforts and intelligence and law enforcement and economic efforts and so forth. And that was, I think, immensely important, Ryan, because you know what we do is we rush to action a lot of times, right? And we don't really understand the nature of the problem. And then therefore, we confuse activity with progress.

• 41:12Ryan Holiday?

  Yeah, I had the historian Tom Ricks on the podcast a couple of months back and his book First Principles. Obviously, I'm familiar with the concept, but I think the concept there is really important, both politically, personally, which is how often are you going back to first principles and going, hey, what do I believe here? What are my assumptions? What's my understanding of the underlying facts here? And then making sure that you measure what you're doing, the actions you're taking, the things you're thinking about, the policies you're developing, making sure that it's consistent with those first principles.

• 41:47Speaker 01

  Absolutely. And I think it's important because these things can kind of take on a life of their own.

• 41:53Ryan Holiday?

  Yeah.

• 41:54Speaker 01

  To subject, you know, these assumptions and to also subject any kind of metrics you come up with, measures of effectiveness that you come up with to kind of a routine assessment, right? So this doesn't happen in government that much, but we set up a schedule for it. And I think my successor dismantled all this, so it doesn't exist anymore. But who I think had more, you know, confidence maybe in his own ability to provide advice rather than a process to give interdisciplinary perspectives and best advice across departments and agencies to the president. But I think, you know, I think you have to set almost a, of course, events can happen that cause you to reframe and challenge your assumptions. But I think

• 42:36Speaker 01

  it's worth putting a mark on a calendar, just saying, okay, every six months, I'm going to return to these assumptions and to look at these metrics and to put a system in place to do that.

• 42:46Ryan Holiday?

  Well, that goes to that idea of stillness. How often do you have time in your life for reflection, for questioning, for, you know, sitting down and thinking about what you think? And I think a lot of us are so busy, we're going so fast that we don't, we go, I don't have time to read books. I don't have time to have this interdisciplinary discussion. And it might be true, you don't have time, but I assure you, the consequences of not having time are going to cost you a lot more time that you don't have.

• 43:12Speaker 01

  Absolutely. You know, one of the, one of the fun parts of the jobs national security advisors, I got to talk with all the previous national security advisors and, and one who was gracious enough to visit me, I think in my first week on the job was Henry Kissinger, you know, and, and I asked him a question, Ryan, I said, hey, how did you find time to, to read and to think and, and think more deeply about, about the work that you do in, in this position? And he said, you know, in that accent, he said, in this job, you cannot, he said, he said, in this job, you will not create any new knowledge, you will consume the knowledge you already have. Interesting. But, you know, I didn't find that to really be the case. He was, he was saying that, I think, tongue in cheek, you know, but, but I, you know, I was, I was, I had the opportunity, obviously,

• 43:57Speaker 01

  to, to have wide ranging discussions. I think it's the way you structure your day, right? So instead of you sitting at the end of a big conference table and saying, okay, I'm ready to be briefed. I mean, set it up like a discussion, you know, do it around a round table, you know? And I think oftentimes too, in government especially, that people have meetings, they, they, they meeting each other to death. Well, how about a working session? Like, how about, how about some whiteboards around here, you know? How about instead of sitting around a, in like a relatively sterile conference room with people putting up PowerPoint slides, why don't we have a collaborative workspace, you know, where we can maybe write some papers in advance, share them, discuss them? You know, I mean, I, I think that the way that we structure

• 44:40Speaker 01

  interactions is really important. I think that one way to do it, like when I was in the job, I would walk across to the executive office building where, where each of the directorates were housed out of the West Wing and meet in, in their own spaces, right? Where they're more comfortable and, and, and, and have discussions that I think were immensely helpful to me. And I think to them as well, right? Because then I could share with them that, you know, the president's priorities and what, what, you know, what I think that, what I think, how we ought to prioritize our efforts to, to craft a new policy or to react to a, a series of events in a particular region.

• 45:16Ryan Holiday?

  Well, my philosophy is you don't find the time, you make the time. And if you don't make it, it's not going to happen. One of the other books that I connected with Shik Tanun about was Cal Newport's book, Deep Work, which he said he reads on a regular basis. He was telling me he has like a room he goes to that's almost pitch black, no interruptions, and it's where he sets aside time to think and reflect and do the tasks that require deep concentration. Because if the leader's not doing that, if the leader's not taking time to think big picture, who do you think's doing it, right? It's not the people below you. That big picture thinking isn't going to filter up to you.

• 46:00Speaker 01

  And as you know, I mean, if you're writing a book, Ryan, I mean, you can't do it like in half hour increments. You know, I mean, it takes a period of long contemplation. And, you know, you're making me feel guilty now because I'm kind of failing at this. So I'm working on another book. And since Battlegrounds has come out, I mean, I've been talking about Battlegrounds too much. I need to really get into like the deep work space myself, right? And start really kicking off into this next project. But, you know, I think you're right. And what you do, I think, when you do deep work and you think and you're more contemplative, you start to make connections that you otherwise would miss, right? And then, and certainly, I think what you do is you begin to discern opportunities. Because I think you do see the obstacle first, right?

• 46:45Speaker 01

  And it takes thinking, it takes imagining how others can be brought in, you know, and how you can approach obstacles from a different angle or different perspective and or make the obstacle irrelevant to you, you know? And so I think that you're right. I mean, this is what we're missing in this electronically connected world. I mean, we are more connected to one another electronically than ever before, but I think distant from one another emotionally, psychologically. And we don't have the kind of discussions like we're having. I mean, who has that these days, right? It's all soundbites and reaction to, well, it was always reaction to the last outrageous thing that Donald Trump did.

• 47:28Speaker 01

  I don't know, what are we going to do now, right? So, but I think it's all about sort of superficial.

• 47:37Speaker 01

  You know, breaking news that is never really breaking news anyway. Uh, and it's, it's people sitting around tables, talking at each other, you know, in a very superficial way. I, I really think, gosh, I worry about the younger generation, you know, they've, you know, I hope that they're reading and thinking and discussing, you know, philosophy and, and history.

• 47:58Ryan Holiday?

  No, it's funny. Like if you and I had connected, we said, hey, let's get on the phone and, you know, meet each other. We would never have an hour long conversation like this. Uh, we, we talked on the phone for 15 minutes and, and it's really though, these sort of in-depth philosophical discussions. Cato famously would, would have these big sort of philosophical dinner parties. Um, I've met Peter Thiel a few times. That's what he sort of has these, he brings these people in and he just has, you know, a six hour dinner conversation. And I think that's really where you can, you know, obviously you, you wake up in the morning and you work on whatever you're supposed to be working on, but it might be an idea that comes to you at dinner, an idea that comes to you at the gym, or an idea on a walk with a friend that unlocks whatever it is that you're struggling with.

• 48:39Speaker 01

  Right. Absolutely. And you know, I'll tell you, what I've found, I don't know how it is with you, but I, these ideas come to me and I think, okay, I won't remember that, but I've got to write it down. I've got to get better at that, you know, I've got to get better at that. So I've been, I've been paddle boarding here lately, you know, so I need to bring a waterproof, uh, waterproof notepad with me.

• 49:01Ryan Holiday?

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

• 49:07Ryan Holiday?

  I, I had a, I had a question for you. We were talking about this idea that, you know, whatever position you're in, someone's been in that before. And then we were talking about some strategic empathy. I'm, I'm curious. So one of the things I'm fascinated in with Stoicism, and obviously I can't go back and ask the Stoics, but you know, Seneca is this fascinating figure to me because here you have this incredibly wise, thoughtful, virtuous, disciplined person who gets the, you know, he gets the call. He's asked to serve his country, to advise the, the, the future emperor. And for a while it goes well, you know, he's, uh, he's, he, the, the, his student seems to be interested in learning. He writes in

• 49:48Ryan Holiday?

  these wonderful essays. They talk. Seneca is this sort of guiding, calming influence at the beginning of Nero's reign. In fact, almost like the first five years of it, historians have very little to complain about, but then. You know, it starts to go off the rails. He stops listening to the advice. And so historians have long speculated like, why did Seneca stay? Why didn't he leave? You know, was he the adult in the room? Or was he complicit? Right? There's all these sort of questions. As someone who's been in a similar position, what do you think is going through Seneca's mind as he watches the, as he watches Nero and as he evaluates his own career prospects and culpability?

• 50:30Ryan Holiday?

  Like, what insights can you give me about the past from your experiences in the present?

• 50:35Speaker 01

  Sure. Well, this was, this was a big, you know, you know, issue with, with, you know, some of my friends, you know, when I, when I was going to go into the Trump administration, you know, uh, these are people who were adamantly against President Trump. These weren't people in the military. There are people outside the military, some academics and so forth, people that I've known for years. Some friendships I lost, actually, you know, but, but I think it begins with really understanding what your role is, right? So for me, you know, I, you know, I, I swore to support and defend the Constitution of the United States when I was 17 years old, uh, when I entered West Point. And I took kind of the extreme position of never voting. I just never voted, Ryan, because I followed George Marshall's example of not doing so to keep that bold line between the military and partisan politics.

• 51:18Speaker 01

  So I viewed Donald Trump as the fifth commander in chief I had served under. And, and, um, and I thought if I had the opportunity to help the elected president make better decisions by running an effective national security process, by staffing him effectively, by giving him the benefit of best advice and multiple options developed, uh, you know, from across the departments and agencies, uh, that that was a good way for me to have a bonus round in my service to the country. So, so that's what I endeavored to do, you know? And, and, um, and what, you know, of course, you know, this is a disrupting, disruptive to many people, very offensive leader, uh, who did not read The Ego is the Enemy, I don't think.

• 51:59Ryan Holiday?

  I'm not sure he read very many books at all.

• 52:03Speaker 01

  And, and, uh, but, but you know, I, I understood what my role was, right? Nobody elected me, right? I still was a three-star general, uh, in the army, lieutenant general in the army. Um, and, and so it wasn't my job to make policy. And if I did, if I was kind of the adult in the room who tried to block the president from something the president was lawfully, you know, could lawfully do as the chief executive or as the commander in chief, then I was undermining the sovereignty of the American people, right? Cause, because only the president and the vice president in that executive branch are really directly accountable to the American people. And if we believe that sovereignty lies with the people, then, then those who assumed the role of, of trying to manipulate decisions consistent with their own agenda or of obstructing,

• 52:46Speaker 01

  like the, you know, this is the, the anonymous writer of obstructing the president's decisions and policies, they're actually undermining the constitution. So I think understanding of role would be the way I'd, I'd answer that. But then also I made the assessment, I made the assessment of, am I making a positive difference?

• 53:01Ryan Holiday?

  Right.

• 53:02Speaker 01

  Uh, and, and, and, uh, and, and, and am I being asked to do anything that's, you know, unethical or, you know, illegal? So if the answer to the first one is yes, and the, and the second one is no, I was going to continue to serve because it was my duty, it was my duty to serve. And, and I, I had really this, this benefit, as I mentioned, of writing Dereliction of Duty, you know, the book about how, why Vietnam became an American war. And one of the curious things I found through historical research is that during the period in which Vietnam became an American war, many of Lyndon Johnson's advisors concluded, hey, we have to tell the president only what the president wants to hear.

• 53:40Ryan Holiday?

  Right.

• 53:40Speaker 01

  Because he, you know, he was basing Vietnam decisions based on his domestic agenda and he saw Vietnam principally as a danger to his domestic goals. Uh, but also because they concluded, hey, I've got to maintain my influence with the president.

• 53:52Ryan Holiday?

  Right.

• 53:53Speaker 01

  Well, it of course begs the question, right? If you're not telling the president what you really think, what good is your influence anyway?

• 53:58Ryan Holiday?

  Sure.

• 53:59Speaker 01

  So I, I never held back, right? And so, uh, there are people who thought that that was, you know, foolhardy or, you know, that I didn't have the emotional intelligence to know that President Trump didn't want to hear some things I was telling him. Of course I knew that. Okay. I mean, and, and I didn't drone on, on long briefings. I tried to, I tried to have really succinct. Give him succinctly the perspective that I thought was necessary like, hey, Mr. President, if we put tariffs on all of our allies, you know, that's counterproductive because if we shoot all of our allies to get to China, China wins. You know, I mean, so that wasn't maybe what he wanted to hear.

• 54:38Speaker 01

  But it was my duty to tell him that, and just what I thought, but what the advice was or the best analysis from across departments and agencies or government and maybe from some of our like minded partners abroad. So, hey, I knew I was going to get used up, Ryan, but you know, in a very stoic way, man, I was at peace with that, right? I was like, okay, you know, when I'm finished, I'm finished. And the way I left, you know, I had a frank conversation with him and I said, hey, I think I'm used up here with you, you know, and, you know, I want you to succeed, but I don't think I'm your guy anymore. You know, when are we going to do this? And so, you know, it was, you know, it was a mature conversation.

• 55:22Speaker 01

  I wasn't, I wasn't in there, Ryan, like, you know, I think a lot of this goes to base motivation in life, right? I mean, I wasn't there to get another job. In fact, when I took the job, I decided I was going to retire as a three star general, right? That was going to be my plan that year in 2017 anyway. And I said, hey, I'm just gonna, you know, even if I'm offered, which I was offered to compete for four separate four star jobs, I respectfully declined to compete because I decided I'm just going to retire at the end of this and go as long and as hard as I can. And then, hey, when I'm done, I'll try to help my successor succeed. I think the president was actually kind of surprised when, you know, I knew that he was going to call me that afternoon to tell me that he had selected John Bolton, right?

• 56:07Speaker 01

  And I said, hey, Mr. President, I want him to succeed, you know, when is he coming on? You know, I'll serve till he comes in and we'll have a smooth handoff, you know, and I did everything I could to make that happen, spent time with Ambassador Bolton and so forth and, you know, set up all sorts of briefings for him because I think, you know, if your ego is under control, Ryan, right? You realize, hey, these jobs, right, your duties, your responsibilities, they're much bigger than any one individual, right? And you hope the president gets that as well. You know, I don't think President Trump actually got that memo, you know, on that. But I think. Um, anyway, sorry to go on about it. You got me thinking, obviously, but I, you know, there were those who said, hey, you should never have done it.

• 56:49Speaker 01

  You know, I would still do it again today, you know, and I, you know, I think his behavior became more and more aberrant.

• 56:58Speaker 01

  After I left, not that I was putting a cap on it. I think it was just a natural evolution of his presidency, you know, beginning with kind of the Helsinki conference and then, you know, then, you know, lots, lots of other aberrational activity in denying the outcome of the election, the, you know, the, the reinforcement of conspiracy theories and so forth and, and false claims of widespread, you know, widespread fraud and then, and then, you know, encouraging this assault on the Capitol. So, um, yeah, I can really only talk about that first 13 months.

• 57:30Ryan Holiday?

  No, I, I think what I'm so fascinated with, with Seneca is that, that, that it, life is complicated, right? You know, the, it's, it's easy to be the philosopher academically. It's easier to be perhaps even just in the, in the more contained world of, of, of your industry or in your case, the military. But then the rubber has to meet the road where we, we, we have to do these things in the real world. And, and there's a fascinating book called Dying Every Day about Seneca and Nero's Court by James Rahm, who's a writer I love. And, and, you know, he's just talking about, um, you know, was, was Seneca motivated by selfishness or selflessness? And it's probably different parts on different days.

• 58:13Ryan Holiday?

  And I think, you know, human beings are complicated and we find ourselves, I, I was offered a, a job as a, as a spokesperson to a cabinet secretary and I'm big not a Trump supporter. And, and what surprised me was even that I considered taking the job, right? And, and, and that's, I think that's also where some of these first principles, and you said the base motivations, what, why do I do what I do? What motivates me, you know? And so you can evaluate these opportunities and dilemmas as they, as they come along.

• 58:45Speaker 01

  Yeah. Well, you've written about this thing, one of your books, you have a chapter on, on, on, you know, being, you know, being part of something bigger than yourself, right?

• 58:52Ryan Holiday?

  Yes.

• 58:52Speaker 01

  And, uh, and you use Admiral Stockdale, who's a hero of mine, who I got to know. In fact, one of my fondest memories was being in the hot tub with Admiral Stockdale.

• 59:02Ryan Holiday?

  Wow.

• 59:04Speaker 01

  It was a Vietnam War conference, you know, and as you know, he had been severely tortured and he was always in pain. And so I went down to work out in the hotel gym and he was in the hot tub. He said, I'm not missing this opportunity. So I jumped to the hot tub with him, had a long conversation with him and got to know him a little bit better over the years. But, but yeah, I mean, talk about, you know, applied philosophy. He's a great example of that.

• 59:32Ryan Holiday?

  Well, I mean, even backing up from his time as a POW, he was, from what I understand, had very few illusions about the righteousness of the Vietnam War. He witnessed the Gulf of Tonkin incident and, you know, sort of saw it for what it was. And, and so, and yet there he was flying, you know, flying missions over Vietnam and then shot down and taken prisoner. And so there did seem to be the ability, you could, you could say it's philosophical or the opposite of, I guess, it depends on where you come down of his ability to compartmentalize his personal feelings from his sense of duty.

• 1:00:09Speaker 01

  Yeah, absolutely. And I think the question to ask is what is your sense of duty, right? And of course, I think one of the great gifts of our democracy, you know, is that we, that we, you know, that we do have a say in how we're governed, right? That, that all of us, I think, can apply a corrective, you know, well short of revolution, right? Just by voting, right? Or demanding better from, you know, from our political leadership. And then I think another great gift is that, you know, our military does swear allegiance to our constitution, right? And, and, you know, I think that, you know, we saw that our democratic institutions and processes put to a stress test in this past year. And

• 1:00:51Speaker 01

  I think we came out pretty strong, you know? And I think that, that, you know, that we had an adjudicative process within the judicial branch of government, mainly at the state level, to adjudicate any of the claims of, you know, of, you know, of false results or

• 1:01:07Speaker 01

  Or corruption in the election process. And then, and then you had, you know, you had, I think, some key leaders, you know, in, in both parties show some effective leadership. I think McConnell's speech, you know, the day of the assault on the Capitol, I think, was, was very powerful, as was the vice president's behavior and, and response to it as well. So, anyway, I, I, I think that, you know, that there is a sense of duty that can transcend this vitriolic partisanship we've seen. And I think it's really important that, that we appeal to that ourselves and in our communities, that we, you know, that we, that we rediscover the ability to empathize with one another, to have meaningful civil discussions about, about the, the issues that are important to the future of all of our children and grandchildren.

• 1:01:50Speaker 01

  And, and, uh, and I think we demand that kind of a civil discourse from our political leadership as well.

• 1:01:56Ryan Holiday?

  Yeah. One last thing before I let you go. One of the things I've been talking to people about is, you know, people go, why didn't the Republicans impeach? Or, you know, why didn't so and so take this stand? Or, you know, why doesn't so and so just do this? And, and I, there is truth to that. As voters, we have to hold people accountable. And, and as you said, you know, officials swear an oath to protect and to serve. But, but I think as philosophers and as students of history, we have to study these things with, with one thing in mind, which is, how do you apply it in your own life? So, you know, it's so easy to go, you know, why didn't these spineless officials do X, Y, or Z? To me, what I want to take from that is, you know, how often do I risk my job for matters of principle?

• 1:02:40Ryan Holiday?

  How often am I willing to say things that will make me unpopular with friends or family? How often am I willing to do a, a thing that I sense is my duty, even if it comes at a great expense to me, personally, professionally, physically? I think at the end of the day, we have to study Seneca, or the dilemma you were talking about in your life, or, or what's happening on the news and say, this is all great theoretically and historically, but how am I applying these lessons in my own life?

• 1:03:12Speaker 01

  Absolutely. And then also to think about, you know, what is in our power, right?

• 1:03:17Ryan Holiday?

  Yeah.

• 1:03:18Speaker 01

  Was it Aristotle who said it is only worth discussing what is in our power, right? And I think what we have to do, and we all have a role in this. We all have a role in, I think, arresting this destructive interaction

• 1:03:34Speaker 01

  between identity politics, or whatever you want to call it, and bigotry and racism. Right? And I think what the Stoic philosophers can teach us as well is they can teach us more about our our common humanity.

• 1:03:46Ryan Holiday?

  Yes.

• 1:03:46Speaker 01

  And help us understand better, even though you're not even supposed to say this anymore, that what defines you is much deeper than the pigmentation of your skin, for example.

• 1:03:57Ryan Holiday?

  Sure.

• 1:03:58Speaker 01

  And so I think that the Stoic philosophers can help us become better people and then also be a source of strength for our society.

• 1:04:08Ryan Holiday?

  Yeah, that's right. Instead of decrying what you see happening in some other state or on the news, or this sort of general, global, or federal trend, it's also like, what are you doing in your neighborhood? What are you doing with your kids? What are you doing in your house and in your relationships?

• 1:04:24Speaker 01

  Right. I mean, are you outraged about inequality of opportunity and the soft bigotry of low expectations? And racial barriers to be able to realize the American dream? Hey, you know, Boys and Girls Club. I mean, all sorts of, all sorts of ways to get involved, you know, that can make a real difference in real people's lives. You know, I think that's the great strength of our country is that we have this entrepreneurial spirit. We have this individualistic spirit that we have can be, you know, it can be, there are disadvantages to it, right? Especially when you say, hey, just wear a mask, man.

• 1:05:01Speaker 01

  But hey, but you know, but there's an advantage to this, right? That we ought to maximize, right? This idea that we can all make a difference. And we have this great benefit of living in a

• 1:05:12Speaker 01

  Where we have freedom of speech, we live on a rule of law. We have to fear somebody breaking down our door without cause, parting us away somewhere. We have the ability to change our lives, people around us, in a positive way.

• 1:05:30Ryan Holiday?

  I love it. Yeah. What can you do in your life with your decisions? And as Epictetus says, what can you do with the matters that are up to me and disregard the matters that are not up to me?

• 1:05:43Speaker 01

  Right, right.

• 1:05:44Ryan Holiday?

  General, thank you so much.

• 1:05:46Speaker 01

  Hey, Ryan. Thank you. I'm a big fan. I'm telling you. I've got, I just want to show you. I just want to show you. Look, you got right here. Eagles, you know me, obstacle the way, tabbed, tabbed.

• 1:05:56Ryan Holiday?

  Oh, I love it.

• 1:05:57Speaker 01

  And lives of Stoics, man. So great to be with you. Thanks for making philosophy so accessible. And I think, I think, you know, reading your books, I think, can enrich people's lives. So it's great to meet you. And I look forward to continuing the conversation at some point.

• 1:06:12Ryan Holiday?

  I totally agree. I'm a fan of your work. And thank you for, you know, doing the unpleasant work of trying to apply philosophical ideas at the highest levels of government and power.

• 1:06:24Speaker 01

  Thanks, Ryan. Take care.

• 1:06:27Ryan Holiday?

  Thanks. We'll talk soon. Thanks so much for listening. If you could leave a review for the podcast, we'd really appreciate it. The reviews make a difference. And of course, every nice review from a nice person helps balance out the crazy people who get triggered and angry anytime we say something they disagree with. So 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.