The Daily Stoic - Leadership Lessons from Gen. Dan Caine | 9/11 Pilot to Chairman of the Joint Chiefs of Staff

Episode Date: April 26, 2025

Just after 2 a.m. on April 11, the U.S. Senate confirmed retired Air Force Lieutenant General Dan Caine as the 22nd Chairman of the Joint Chiefs of Staff. As it turns out, Ryan had the opportunity to interview Gen. Caine a few years ago as part of The Daily Stoic Leadership Challenge.In honor of his recent confirmation, today’s episode is Ryan and Gen. Caine's powerful conversation. Gen. Caine reflects on being one of the first pilots in the air on 9/11, the core traits every great leader must embody, and how to effectively inspire and guide a team toward a shared mission.General Dan Caine is the 22nd Chairman of the Joint Chiefs of Staff. He has flown more than 100 combat hours in F-16 aircraft. His total flight hours are 2,800. Throughout his career he was awarded the Defense Superior Service Medal, Distinguished Flying Cross, Bronze Star Medal with bronze oak leaf cluster and the Defense Meritorious Service Medal. 💡 Want more insights from extraordinary leaders like General Caine? Check out The Daily Stoic Leadership Challenge at store.dailystoic.com.🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us:  Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can listen to the daily Stoic early and ad free right now. Just join Wondery Plus in the Wondery app or on Apple Podcasts. water damage in your home. There are many options you can explore to help prevent this. One way to help minimize the risk of water damage in your basement is by installing a device called a sump pump. A sump pump usually sits below your basement floor and moves water out of your basement if the water level in the sump pit gets too high, helping to keep your valuables dry. It's also recommended to have a backup power source for your sump pump to ensure it continues to work in the event of a power outage. The Home and Auto 101 Report powered by TD Insurance.

TD Insurance offers home insurance that helps protect your home and personal property with coverage that suits your needs. To learn more about the differences between standard and optional water damage coverages, visit TDInsurance.com. Hi, I'm Lindsey Graham, host of Wondries Business Movers. In our latest series, young British entrepreneur Richard Branson launches a music retail store, but he ends up behind bars

when authorities discover he's not paying taxes, forcing Richard to rethink his rule-breaking approach to business. Listen to Business Movers, Virgin Territory on Amazon Music or wherever you get your podcasts. 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, and most importantly, to prepare for what the week ahead may bring. Hey, it's Ryan. the week ahead may bring. sex with like headline news, I guess, right? Like we just did that bonus episode with Rory McElroy and the Masters, obviously that's surreal.

You're sort of watching TV, this great sports victory, and then somehow a sportscaster's like, actually this has to do with Ryan Holiday's books and Stoicism. That's certainly not what I was thinking when I wrote a book about an obscure school of ancient philosophy, but I'll take it, right? It's humbling and mind-blowing and very, very cool.

There was another one of those, again, sort of surprise things when I saw the news that General Dan Kane had been selected or picked to be the 22nd chairman of the Joint Chiefs of Staff. I think I was at a Spurs game actually. I pulled up my phone, I looked at the New York Times app and I saw the announcement. I go, wait, General Kane, I know him.

We sat out back at the painted porch and talked about philosophy. I interviewed him for the Daily Stoic Leadership Challenge. We text back and forth. And here he is being nominated to one of the most important and influential positions in the world. If you don't know what the chairman of the Joint Chiefs of Staff is or does, it's basically the nation's highest ranking military officer. And their job is to be the

principal military advisor to the president, to the secretary of defense, and the National Security Council. I guess this isn't the only stoic who has held a position like that. General H.R. McMaster, who's been on the podcast, was the National Security Advisor to Trump in the first term. We've talked about his work today. But my conversation with General Kaine

was an eye-opening one for me. He talks about being one of the first pilots in the sky on 9-11, how you have to adapt as a leader and why you have to always be learning as a leader. One of the things that I took from the conversation, he was telling me that he thinks he's given a direct order like twice in his life. Like we think of military leaders, especially maybe someone who's head of the Joint Chiefs, to be like, do this, don't do this. And he's talking about how actually that's not what leadership is. That's what leadership is in the movies,

but in real life, it's something much more collaborative, much more connective, much more relational. So I thought that was really interesting. The Stoics have a long history of being influential at this level, not just being veterans and serving in the military. Rutilius Rufus, who I talk about in Lives of the Stoics, is sort of considered one of the great trainers of troops in the military. Rutilius Rufus, who I talk about in Lives of the Stoics is sort of considered one of the great trainers of troops

in the ancient world. There's a Stoic general named Scipio, who's part of the Scipionic circle, who I talk about also in Lives of the Stoics. And so I interviewed General Cain for the leadership challenge, we're talking about leadership, but that was just inside the leadership challenge.

And so today I wanted to bring you that conversation. In his opening statements for his confirmation hearing, he said that, "'Our national defense requires urgent action and reform across the board. We must go faster. We must move with a sense of urgency.'" And at 2 a.m. on the 11th, the Senate did confirm General Kaine.

He's now the chairman of the Joint Chiefs of Staff. Although he was appointed by President Trump, a president that I have been quite open about my profound disagreements and doubts about, this is not a political episode because this was recorded first off several years ago. And second, the chairman of the Joint Chiefs of Staff is a non-political position in the sense that they are just supposed to be concerned with leading the country, making sure that our defense is handled, making sure that America's obligations all over the world are properly managed. It's a position of immense responsibility and obligation. And I think General Kaine is a fundamentally decent

human being, a man who has selflessly served this country for many, many years. But I guess what I'm saying is that this isn't like, we're not talking about political stuff here. We're talking about leadership. We're talking about duty. None of the stuff that is unfortunately infected too much of the rest of our government and culture these days.

So none of that in here. And look, General Cain is not just some administrator. He's flown more than a hundred combat hours in the F-16. He has something like 2,800 flight hours. He was awarded the Defense Superior Service Medal, the Distinguished Flying Cross, the Bronze Star, and the Defense Meritorious Service Medal. This is one of my favorite conversations that I've had here at Daily Stoic. And I'm excited to bring it to a wider audience.

The Daily Stoic Leadership Challenge is one of the best things I think we've done here at Daily Stoic. We interviewed, as I said, generals, we interviewed CEOs of sports franchises. We interviewed elected leaders, entrepreneurs, experts, to give sort of real practical leadership advice, Stoic leadership advice, for how to do what the Stoic said we had to do, which was be in the arena, be in the room where these things happen. That's our obligation.

And I'm excited to bring you this episode. We have an awesome guest today. So if you wanna get your questions ready, you can put them in the chat or just get ready to raise your hand. But General Dan Kane, it looks like he's on. Hey, my friend, how are you? Good. Good to see you. Thanks for the invite. Of course. You're early. I wouldn't expect anything less though.

Hey, it's what you got to do, right? Where are you right now? I'm about one mile south of the Pentagon here in Crystal City, Virginia. So just hold away in our small apartment here just down the road a bit from work. Wonderful. We'll let some people log on here for a second and then put in their questions. But how have you been? I'm good. Yeah, I think that's a better question for you given the road trip. I saw you guys were rolling through Arizona and I don't think I caught you in time to say, go check out Frost, that great gelato place.

No, I'm thankfully not in Tucson, although it looked like I was gonna have to spend an unnecessary amount of time there. Although there's an Air Force base in Tucson that asked me to come speak, I haven't made it work, but my son was very excited about the graveyard of planes that they have there. Because we drove by it.

I know it well. Yeah, I've spent some time inside the graveyard of planes. In fact, some of the airplanes I've flown are now in the graveyard of planes. And I actually rescued one time out of there. And now it's here in DC. I bet that graveyard is bigger than many countries, Air Force, Air Force, it is it's actually a moneymaking venture

for the United States military through foreign military sales, parts and things like that. It's actually a profitable business, like the mothball fleet, that is the mothball fleet. So much like that the Navy has sort of stationed around on the eastern seaboard. And there's routinely airplanes that will be refurbished and come back out of there. Sadly, many of the fighters that I flew as a youngster are now being turned into to missile drones where you shoot missiles at them. And

oh, well, so when I was at Aviano Air Force Base right before the pandemic, and they let me sit in an F-16, and they were showing me the numbers on the tail or whatever, and the plane was two years older than I was, which was a tad alarming. Dude, my dad was in the first group of guys to fly the F-16, And the jet that I soloed when I was a young lieutenant

was built, those numbers were built in 1978. And that is a jet that he picked up at the factory and is the jet that we rescued from the Boneyard there in Tucson, so. I'm not sure if that's encouraging or terrifying. I think you get good value for your money. I mean, the taxpayers have gotten a good return on their investment over the many years that those airplanes have been around.

When they showed me one of the one of the bombs that was in the in the hangar or whatever, they were like, we manufactured this to drop on Vietnam. Yeah, yeah, that's that, that's also a little scary. But most of those weapons are out of the inventory now. We've got better bombs. Well, one last story. On the road trip, I was driving. We were driving back.

We went up to Cerro Gordo, which is where I recorded the last episode of this, which is this ghost town in the mountains of California. And then so we were driving back instead of through Tucson, we went through Flagstaff, then Vegas to I forget where we stopped in New Mexico. But we stopped for gas. I we pass an Air Force base, we stopped for gas. And across the street from Creech Air Force Base. Oh, yeah, yeah, I heard about this. And some kids got that is so awesome. He's got the first signed copy. Yes.

So it's a sort of weird thing where you can kind of recognize that someone recognizes you and they're not sure if they are going to talk. So it's kind of weird thing where I could tell that he and his wife were talking about me and deciding whether they were going to come up. And they did. And yeah, and I looked them up. He's just been promoted to master sergeant a few weeks earlier.

And he happened to be reading the book in the car when we pulled up. So it was meant to be. I'll chat him up and tell him you were asking about him. You should. Do you know his name? I can get it from you. I think I saw it on Instagram or whatever,

but I'll send him a note. And I was just chatting with Joe Briarly too, who said you're getting ready to do his, from the Green Notebook, I'm sure. Yes, I already recorded it. I think it comes out this week. So very small world. Well, look, I'm very excited to talk with you comes out this week. So very small world. Well, look,

I'm very excited to talk with you. Just a couple of housekeeping notes for everyone. If you have questions for the general and myself, put them in the chat and or the Q&A or raise your hand. I think you can just ask your questions. I will read them out. But in the meantime, we'll get into it. I'm very excited to have this conversation. I appreciate you giving us the time. I know you've got a lot of important things going on, but I wanted to start with 9-11 being, this is the 20th anniversary.

We've talked to a bunch of interesting leaders in the course of this course, and they've been through some crises and difficulties, but nothing quite like being one of the first planes in the sky on 9-11. So could you maybe walk us through that day and what that was like? Of course, yeah, it's hard to believe it's been 20 years, you know, last weekend and it's just strange to look back on that. On September 11, 2001, I was actually stationed here in Washington, D.C. out at Andrews Air Force Base. I was flying F-16s. I'd been to the Air Force's Top Gun school where we don't play much volleyball. We mostly focus on getting better as tacticians

with a little bit of jest towards my Navy brothers and sisters. And we had just gotten back as a squadron from out in Las Vegas at Nellis Air Force Base where we were getting ready to deploy. And that Tuesday here in Washington was a beautiful and gorgeous day. And I was not scheduled to fly that day.

I was originally sort of running the flying operation for the squadron as the chief instructor and tactician. You know, as we came in that morning, we obviously had no idea what we were going to face. And we were in a meeting at the squadron, just a training meeting when one of our young intelligence professionals came in and said, an airplane has has just hit the World Trade Center. And of course, my first thought was, it's a small civilian airplane, this couldn't be. And as you get older, as leaders, you start to develop that spidey sense of just something's

not right. And I felt that got up, walked into our squadron lounge where we had a big flat screen TV. And remember, I still get chills today even remember clearly the helicopter news shot showing the first tower burning when the second airplane flew into the picture and hit the building. Silence, could have heard a pin drop and we sat there for what seemed like a long time,

which was probably just a very few seconds. And I went to the desk where we had all of our communications gear and I picked up the phone and called the Secret Service and said, I don't know what's going on, what do you need us to do? We had a relationship with the secret service in Washington because we flew out of the same airfield as the president. The next phone call was the White House saying, get anything you can airborne. The nation is under attack.

And right at that point in time, my boss, Brigadier General Dave Worley walked in and I handed him the phone and I said, hey sir, this is for you. And we went and got ready to fly and it was myself and a wingman and there were two other folks as well and we got our gear on and went running back to the ops desk and met General Worley. General Worley read us the rules of engagement for defending the National Command Authority.

It was very liberal and it was on us. And when you think about leadership for the folks on the call and on the video here, I will never forget what then General Worley said to us. He's just read us the rules of engagement, which are extremely liberal. The decision is clearly mine as the CAP commander, the mission commander over the combat air patrol. And he reads us verbatim. And then he pauses and he looks at us and says, Hey, Dan, look, I don't know what you're going to face out there. I think

you're probably going to have to make some very difficult decisions. But here's what I want you to know. I trust you, you're going to do the right thing. And no matter what, I have your back. And you want to talk about saying the exact, exact right thing at the exact right moment. We ran to the jets and scrambled and we're flying that morning. We took off, I think, right around the same time that the real heroes or some of the real heroes of that day, the passengers of Flight 93 were assaulting inside the airplane, knowing full well what they were facing, knowing what had happened in New York City,

and yet finding the courage to step up, not having taken the same oath that we take to uphold and defend the Constitution, but knowing that their nation needed them to do something. So flew that the rest of that day, and a lot of intercepts and a lot of sort of keeping, keeping airplanes away from downtown Washington. And our squadron flew for the next 45 days after that.

And I deployed pretty quickly overseas to start fighting Al Qaeda. Well, to bring all that together, I think there's a couple interesting themes. So one, which is open lines of communication. I think it's pretty incredible that you're just sort of very quickly on the phone with the White House.

I was reading a book about Admiral Rickover recently, that they just sort of mentioned it offhandedly, but I guess for maybe it's still the case, but it was the case during the Cold War, that every commander of a nuclear submarine could directly call the White House. Like there was just a phone they could pick up and it would ring at the president's desk.

And so I think sometimes we think these organizations are huge and there's this massive chain of command, but at the top, it sounds like- Well, they called us just to be clear. I called the Secret Service. But that's what I mean. That's what I mean.

Yeah. Is that at the end of the day, the really elite operators have to be completely flat. There has to be open lines of communication and flexibility there. Flatness is something from a leadership perspective that we value greatly. Certainly I value greatly and I drive the organizations

that I'm blessed to lead or be a part of towards that flatness. I think as leaders, if we don't understand what is happening at the edge of the empires that we're blessed to lead, serve and help with, then we can't possibly understand what's really going on. So flatness is a key to that. Yeah, because often, you know,

I think especially at the lower levels, you can be like, well, I pass this up the chain and something will happen. But I think it's interesting that, yeah, you called the Secret Service. You didn't sort of wait around and say, let's see if somebody needs me, let's wait to see where this goes.

You sort of use the contacts you had on that day to sort of say, you know, what do you need from me? What can I contribute? What's going on? I think we've got a responsibility as leaders at whatever level you're leading at at to be proactive and not reactive, to realize when there's a white space and lead your organization or yourself towards that white space to improve the overall effectiveness, efficiency, combat, whatever kind of organization you're leading, and move towards the problem.

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You can binge business wars the Whole Foods rebellion early and ad free right now on a wonder E plus When that goes to the passengers on flight 93, which you texted me a transcript of that call on 9-11, which I was, it always sort of gives you the chills to read. I think the idea that, yeah, they weren't sort of technically leaders in any way. It was, you know, a handful of people talking on phones on airplanes, which I think younger people don't even remember was a thing that you could swipe your card and get a handset out of the back of a seat. But they sort of anointed themselves leaders.

And it was, I thought it was remarkable is that you have this 911 operator relaying information from all over the world, sort of that all these people involved, although they had no official authority or even official obligation to do anything, took it upon themselves to say like, look, we might not be able to solve this thing,

but we can not contribute to the problem. We can not make this tragic event more tragic, and we're gonna try to do something. And I, you know, I just, I think about them every day, tragic event more tragic and we're going to try to do something. And I, you know, I just, I think about them every day. Right. And that is real courage knowing what is going on in the United States at that point in time and having the intestinal fortitude, the bravery to stand up and go forward, knowing it's just an incredible example.

You know, America started to fight back immediately, and they were the first steps. The firefighters that headed up buildings were the first steps. You know, the people at the Pentagon were the first steps. And out of this tragedy of September 11th, we can find incredible goodness on who we really are as a country. And I hope we just always take advantage

of those examples moving forward. Yeah, you know, it's almost easy to celebrate the firefighters and the police officers, but there were also the office managers and the employees and the people who had, you know, they worked in this enormous office together, but never met before. And again had no real obligation to anyone but themselves and decided, hey, I'm not leaving anyone behind or hey I'm going to do what I can here. That is also what leadership leadership isn't this thing you get promoted to necessarily it's also what you do in moments of crisis. Absolutely, absolutely. It could have been a lot worse that day at those people not evacuated the towers and those people stood in the stairwells helped other people get down there people in the Pentagon could have been a lot worse.

Or that plane you know flight 93 could have crashed into the White House or Capitol building. Would have been much worse. And then when I think about leadership, although thankfully you didn't have to, it strikes me that what your commander was talking about was the idea that within the latitude that you had been given, you would have, you potentially would have to make some very hard decisions in the moment, which is also something we've talked about, but sort of the definition of leadership to me is, you know, can you make hard decisions with limited information and limited time? Yeah, you know, and as I reflected on that day, and look, we just did our jobs.

We just did our jobs and thankfully we didn't have to make the decision to shoot somebody down as I reflected back on that day and folks have asked me, you know, where are you scared or what, or what was going through your mind and whatnot. I mean, of course, but overwhelmingly the thing that, and I'm grateful for this experience in some ways as a leader, my largest concern was not to miss somebody and not to be able to prevent or be unable to prevent

an airplane going into the White House, going into the Capitol. And that drove everything. And I didn't realize it at the time. I was younger and a young captain. But as I've reflected on that over the years, I'm grateful for that and other situations like that, where I built some trust and confidence in my own instincts as a leader to be able to make

difficult and complex decisions with limited information in short amounts of time. And that is something that I've learned to value greatly. Yeah, and it strikes me as similar to the idea as we talk about sort of different organizations and how they're structured, that what the your commanding officer did there was give a really clear sense of what sort of commander's intent was. Like he was like, this is what you're being tasked with. These are the legal constraints that you have to operate on. Here's what I expect of you. And then he said, the rest is your call, right? He sort of trusted that your training, your judgment,

your conscience, you know, your sense of duty would take care of the rest. Absolutely. And clarity of guidance, especially in today's day and age and how you think, develop, and then articulate that guidance is so important to organizations and so important to leaders to get it right and get it out there and stay consistent on what that guidance and intent looks like.

Because in the end, what that drives towards is what is the culture that your organization is going to embrace and how are you gonna move the organization from where it is now to where it probably needs to be. And Gerald Worley, who tragically, in a horrible story after he retired, was volunteering with his wife

at Walter Reed Army Medical Center and they passed away in a metro rail accident in Washington, DC, instantly killed the two of them together. And so I went to see his grave over the weekend and talked with his family, but getting that clarity, guidance, and intent right, and then being consistent over and over and over again on what that culture has to be in order

to achieve that end state is really important. And a lot of that comes down to sort of boiling it down to the ability in my mind to understand what is the situation, the context, the resources that you have, and then bringing those elements together into guidance and commanders intent. So how can leaders get better at doing that? Because I know, like, when I often look at mistakes that people who have worked for me or people I'm on a team with have made, it almost always comes down to us not being on the same page about what was expected. And it's usually my fault. Like,

usually I didn't explain what I wanted. By the way, I'm the same way. I'm always like, you can ask my teams, I'm constantly saying, man, I F that up. I could have been a better leader. I think humility, authenticity, candor, and realizing that we're all students at this, no matter whether you're a business leader, an educational leader, or a general, or admiral in the military, you gotta go to school on it. And I think back to your question, you know, I've spent a fair amount of time over the years thinking about how do I best

understand the situation that I'm dealing with. And it started when I was a young fighter pilot before I became a special ops operations officer. And it was how can I learn everything about the adversary or the situation that I'm dealing with and that started this journey of insights for me. You know I used to think about who am I fighting today, what kind of airplane are they in, what did they do yesterday at work, did they go to sleep last night, what do I think they ate this morning, what's the weather like, what how's their airplane configured? How did I sleep? What's going on with me? How did I prepare? And just starting to think deliberately about asking really good questions to try to understand all the subtleties and the big levers, but also the subtleties of

the situation that you're dealing with and trying to bring your organization into this conversation so that you can get an aligned stacking of hands on what the problem is. Defining the problem and understanding the problem together, I think is a key to gaining that understanding and context of the situation you're dealing with. And you're right, man.

I'm in the exact same place. I think defining the problem is very key. The other way I think to look at it, then I'd be curious your thoughts. I guess this is a tad more important in the civilian world, but it certainly would make sense in the military world, which is defining success. Like what does success look like?

What does this problem being solved look like? Because if we don't know what success looks like, how do we know how far to go? How do we know when we've arrived? How do we back out a solution if we haven't solved for what success is? And I think that to me is the most essential role of a leader, whether it's a sports coach,

whether it's a board of directors, it's a CEO, or it's a sports coach, whether it's a board of directors, it's a CEO, or it's a person who's hiring a freelancer to help them on something, which is where are we trying to get here? What does success look like? Because there's lots of different forms of success for every project or person.

And if you don't define a really constrained specific version of success, you might get a solution to the problem, just not the one you want. And you're going to experience creep, you know, we're both friends with the Texas Rangers and you know, I'm chuckling because I've asked our mutual friend Chris Woodward many times. What are we solving for? Yes. mutual friend Chris Woodward many times, what are we solving for? And what do you mean by that? You know, and I think as leaders and especially for this great group of leaders who've taken the time to join this cohort to sort of think about leadership, it comes down to that clarity and asking real questions. And I find even for me, who I'm old and tired,

but I still find that a decent amount of the time, I'm not really asking the right question or we're not talking about the right thing. It's until you get to that root cause, that root area of specificity with, oh, by the way, even in business, because I spent several years as a business guy, even in business with enough specificity

that then you can go measure, it is what you need to measure in order to determine whether or not you're on trajectory or off trajectory to achieve that end state. And then having those routine stops along the way to make sure that you're pausing and assessing, are we headed in the right direction or not? And that sometimes helps avoid creep as we move forward.

It strikes me that the tragedy coming out of 9-11 from the civilian side is that we don't give the military, who I think has done a pretty good job of the last 20 years, we don't give them great guidance and clarity on what success looks like. So we call it the war on terror. Well, what does that even mean?

What is success? What is the actual outcome of Afghanistan or Iraq? We could put all the politics aside. I think the problem or the inherent difficulty in both of these ventures, which is an inadequate word, but it wasn't completely clear what we were doing, what success was supposed to look like, how long it was supposed to take,

and is that where the creep comes from and where the confusion comes from and then the difficulty extricating comes from is that you can have the most talented people in the world, the most dedicated people, the most committed people, the brilliantly equipped people in the world. But if it's not totally clear what they're doing and how they're supposed to succeed, they're probably not going to be able to do that. Yeah, and there was some, you know, super talented folks who in the last 20 years have been in the middle of exactly what you're talking about. You know, I'm a, and we've talked about this, I'm a addicted reader. I'm your dream customer because I buy the hard copy, buy the audio, and buy the Kindle book. And I look forward to the next one, by the way. I would

encourage everybody on the Zoom call to read the Afghanistan papers, which just came out, ironically, prior to the president's decision to leave. And I think you'll find in there, again, staying away from the politics of the decision, given that I'm an active duty military officer. But I think you'll find in there some very important nuggets and lessons about clarity of end states and some interesting things to think about as we look at the way this amazing country of ours

that is the is the best, worst system out there as our founders said, but it's difficult in transitioning administration over administration. You know, it's been I think for anybody in the military that's on the net or anybody that's spent any time over there, this is a bit of a challenging chapter to sort of see all of these things play out. Again, not a political comment. I support the president's decision, but the trying to achieve and driving towards clarity of an end state and then sticking to it, which is hard to do,

I think will be what we learn out of this. Yeah, I think that's right. And one of the things I wanted to ask you, because as we talk to different kinds of leaders and I've talked to different leaders over the years, there's kind of this envy that like envy or almost despair, it's like, hey, this isn't the military. I can't make you do stuff. Right? Like we think about, you know, if you're the CEO of a

company, you have some control over the organization people, but, you know, much less, I think people speculate than if they were, you know, sort of members of a regiment or, you know, you were a general or something. But I think the operative word you used was guidance, right? Commander's guidance or commander's intent. Is that a myth? Like even in your organization and your line of work, is it still much more about convincing people to do things as opposed to being able to make them do things? Right? Like, talk to me about that. Yeah, I mean, I think if you're a leader in today's military that has to say, I'm ordering you to go do this, then we've got much bigger problems.

And I have never, that I can remember, said, I'm ordering you to go do this and making somebody do something against their will. I think world-class leaders, and I have a long way to go till I'm a world-class leader, are people who can use EQ as much as IQ and influence followers to get to an outcome that they want without using overt directive force or rank to make that happen. There is a certain level of respect, if you will, or deference that comes

with rank in the military. But when I was in the private sector for a few years, I worked with a bunch of young, right out of college graduates who couldn't give a rat's ass what I did in the private sector for a few years, I worked with a bunch of young, right out of college graduates who couldn't give a rat's ass what I did in the military. And it was all about my ability to connect, build rapport, sort of lay out the why behind we wanted to go do something, and then motivate, inspire, incentivize, encourage, love, occasional kick in the ass to go do this. And they were fantastic. And so I think we need to be careful in civilian contexts to think that the military, of course, there's a rank structure and all that, but I just don't see. And of course, I do acknowledge I'm coming at this conversation as a two star. But but I the same I use the same approach when I was a captain, a young guy.

I think great leaders influence through adaptive, dynamic, repetitive processes that allow them to connect with people, understand where those people are coming from, and then clearly communicate where the organization is going to go, and then lead by example to bring that organization, whether it's a civilian business or it's a government entity, towards that end state.

Yeah, there's an Eisenhower quote that I love that I think I talked about on the last session, but he said, the art of leadership is getting people to do things because they want to do them, which I love. You think about the immense power that he held, probably in all of history commanded the most men, the most power, and hopefully nothing like that will ever happen again.

And he's still thinking, you know, about persuasion and incentives and alignment, not force. All the time. And I mean, that's what I'm in the Pentagon working for the secretary across the interagency with outside organizations or with the various military services, that is what's running through my head. Not I'm talking to so and so or such and such and they're a particular rank. It's what's going on in their head. Where are they coming from? What is their motivation? What are

they trying to achieve? What am I trying to achieve? How do I achieve compromise? Or if not, how do I recruit them onto what I'm trying to do through influence? I mean, Marshall, which you and I have traded notes on Marshall, Marshall was much the same way, right? I mean, these fantastic examples of stoic leaders who understood the sort of human power of influence and persuasion without having to walk around putting their rank in their face. And MacArthur is a completely different case study, right? Yes. Well, and I got to imagine that as the military

gets more diverse and more reflective of the civilian world, all these things take on even more significance because it's not a bunch of white dudes from the same place, the same backgrounds, the same experiences, the same shared assumptions, bossing each other around. It's having to really connect and understand where different people are coming from with different experiences, different priorities, different ways of thinking and figuring out how you get them all on the same page, as opposed to I am ordering you to do this and you should be afraid of me. So don't don't ask any questions.

Absolutely. And I think that comes down to how in tune with understanding culture, and then adapting that culture towards what you need to get it towards. And then being able to drive it home over time. And it involves, you know, this really I don't think you're going to be effective in the future. And so that's what's so wonderful about all of the folks on the Zoom and the call here. They're all investing in time to develop their leadership skills and traits to be a broader set of tools.

That brings up something important, this idea of being a student of leadership, right? That it's not something that you just pick up because you're naturally charismatic or because you're brilliant. Walk me through your journey sort of studying leaders. Are there some that you really admire? You talked about reading. How is your education as a leader gone outside of just, you know, trial and error and experience on the job.

I definitely, you know, and you're so great about getting this quote out there, all leaders are readers, but not all readers are leaders. And I think Truman got it right. And I think the ability for me, you know, I started out as a young fighter pilot and then went on to sort of scale through that.

And then did a White House fellowship in DC, which allowed me to gain real insights into civilian leaders and sort of into the special forces community and back into business and sort of bounced in and out of government over time. The consistent theme through all of that was this real sense of humility that I wanted to be a leader worthy of those amazing humans that I were blessed to be in the leadership of, whether it be in the private sector, in business, or it be in the military or it be in the interagency. And so reading was the thing that allowed me to accelerate those insights. And it has been a part of my life since I was in college. I just, I can't get enough of it. And there's not enough time in the day that I can read. I read a book a week, typically. I mean, what I

try to do is to be thoughtful and intentional about what it is that I'm reading based on the jobs that I think I'm going to, so that I'm prepared ahead of time. Or if I'm encountering a situation, I'll go seek wisdom of others who've been in the same situation. So I've read a lot of Marshall and all the Forrest Pogue books on Marshall.

I read David Rohl's book on Marshall that we traded notes on. I had him on the podcast. Yep, absolutely. And what a great guy, very kind with his time. You know, recently been curious about the relationship between the Department of Defense and the intelligence community. So I'm reading about that interaction.

I of course took a spin through World War Two history. I'm curious about the rise of China and and the juxtaposition of the fall of great societies. Routinely, I read this great book called The Daily Stoic. You've probably heard of it. But I think history repeats itself over and over again. And as leaders, if we're not mindful and deliberate about learning those insights, then we let down to a certain extent, those that were given the gift of leading.

And I don't wanna be that guy. I've always sort of worried that I'm not gonna be worthy of the gift of leadership. And so I'm pretty serious about it. And I enjoy it. I mean, sure. No, and I love General Mattis's book, Callsign Chaos. He talks about this a couple times. He says, one, it's not sort of that you can read. It's whether you are reading.

And he talks about it. I really liked his concept of being functionally illiterate. If you have hundreds of books about what you do, you're functionally illiterate, right? Which is almost more embarrassing than being actually illiterate. And I thought what he was saying about your line of work that I think is particularly important, and I think just a slightly less high stakes version of it is true for all of us,

he was basically saying, you can't learn on the job when you're sending people out into battle because you're going to be learning your lessons at their expense. He's like, you can't be filling body bags as you figure it out as you go. And I think that's, you know, you're entrusted with people's time, with their careers, with the best years of their life, you know, in the civilian world, the idea that you're going to make a bunch of mistakes and have to lay people off or put people in the wrong role or not know basic things that you could have figured out by reading a book is not just stupid. It's very disrespectful and wasteful of what these people have entrusted you with. So I like that you said that. I couldn't agree with you more. And I

think it's a responsibility that we all have as leaders to be as prepared as we can be and to be voracious readers across our entire career. And then after that, I think it just goes to being a good human, learning the lessons of history and preparing ourselves as much as possible. Well, and this is a thing I think for leaders, it's like whatever position you're in,

whether you just got promoted to sales manager or you're the executive of a Hollywood studio or you just got, you know, you're a rookie in the NFL or you're a, you know, you're a mid shipment at the Naval Academy. Somebody has been there before and written a book about there is a memoir about basically everything that's ever happened. And so the idea that you would not want to experience the thing multiple times, I think Milan can bear in the unbearable lightness of being me,

is this great line about how the problem with life is that you only learn by doing stuff and you only get to do everything one time, right? You don't get to run your life over and over again and take the optimal path. But I would push back and say reading is the one way that you get extra cracks at something. You wanna learn from the person who was a congressman

and screwed it up. You wanna learn from the person who was a congressman and then became president. You wanna go through the different cracks or run-throughs or reps of whatever you're going through and then hopefully build on that as opposed to being, the first whatever you just got promoted to and acting like you discovered, Tara incognita

and that this is all brand new fresh territory that's never been explored before. Well, that goes to the genuineness of humility and being worthy of the command that you're given or the leadership opportunity that you're given. When you're young and you get into your first management role, you know, you probably think, I got this but I sure, I sure maybe early on did. And then I realized I have so much to learn. And I still feel that way today where there's just this genuine desire to be as prepared as I can be.

And that translates into a lot of reading and always learning, you know, I, and I think it also, to your point about reps, we don't get a lot of reading and always learning. And I think it also, to your point about reps, we don't get a lot of them. And I think there's this decay, and this is why I think this program is so great. I think there's this decay in American leadership across the entire continuum, government, business, industry, you name it.

And only through accelerating insights are we going to gain the traction and the proficiency needed to be who we can be as a country. And I know American exceptionalism and the meritocracies are starting to degrade a little bit. And when you flick past that outer shell, how much breadth and depth is in there and subject matter expertise and leadership? And it's a little concerning. No, I was just reading something about China. And I'd never thought about it this way. And it was interesting. They were talking about how almost nobody in the Chinese military has any combat experience. Because China has been

isolated for so long and didn't get involved in a number of global conflicts that we have. Outside of basically their brief involvement in the Chinese war against Vietnam and then some UN joint missions, almost no one in the Chinese military has any actual combat experience. It struck me as one, obviously experience is a great way to learn, although it's very costly. And so you could see that as both a blessing and a curse, but it also struck me as like,

they better be doing a lot of reading, right? Because you are missing, by not having the firsthand experience, you're at an enormous disadvantage, as costly as some of the mistakes and blunders that America has made over the last 50 to 60 years. They have been educational in a lot of ways. We've failed to not always learn the lessons,

but I was thinking about, you know, how if you don't get a lot of reps, it almost increases the need to have to be an avid student of whatever you're doing, because you're having to make up for lost ground. Yeah, and I'm pretty sure the Chinese are reading all of our books. So, I'm probably trying to get into a lot

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and brand new episodes on the Wondry app or wherever you get your podcasts. You can binge the original series before anyone else and completely ad free on Wondry Plus. anyone else and completely ad free on Wondry Plus. Well, what does your reading routine look like? Cause you mentioned you read in all the formats. How do you think about it? Yeah, I mean, my days are somewhat set

at this point in my life. You know, I get up between four and 415 and I- Why? I'm an to really rise. You're on the Jocko track. I think I normally beat Jocko out of the rack. So a good way to start the day, beat the seal out of the rack. And, uh, you know, I'll, I'll read hard copy books then.

I read some philosophy. I read some faith stuff early on. I do some journaling in the morning, I've been doing this for years and years. I'll write letters to my to my daughters every morning and send them something on text or Instagram. And then I'm religious about working out, I get to the gym early on in the morning between six and 630. I'll listen to books in the gym. I'll listen to podcasts in the gym. I'll then sort of come back and get ready for work. I'm listening to a book on tape going in.

I'll occasionally take a scan through the news, but if the crap hits a fan, we'll hear about it. And I think American mainstream media is struggling a little bit with antiseptically presenting facts. So that's not a political comment, just an anecdotal comment. And then I keep my Kindle generally up to speed with the hard copy books because I travel a fair amount and I'll haul that with me and move forward. At the end of the day, I'll come back. I'll do some decompression and some thoughtful thinking about the day.

How did it go? What did I do right? What did I do wrong? How can I be better? I'm a guy who's got always carrying around three by five note cards or four by six note cards. So I'm taking notes there and then putting them into the Evernote, which I've been using since like 2007.

And then I go to bed, I'm super exciting. I'm going to bed around eight, eight 30 at night. And the next day off to the races again. But I'll tell you the morning ritual has been so good for me. It is so important to start that day with thoughtful, deliberate stillness before the craziness of the day starts. I think you got it right in your book about stillness really being the key. And I just really strongly advocate for that

with all the people that I mentor and help grow as leaders. I think it just makes us so much better as humans. And we're fallible. If we don't take care of ourselves and our families, we can't possibly be the leaders that the folks we lead deserve. I've got to imagine seeing your fair share of raw recruits or

sort of people from civilian life coming into the military over the years. How do you talk to someone who's sort of not a morning person and make them a morning person? Right. Like, what is that? Because I see this question a lot and someone asked it. But like for people were like, oh, I could never get up at 4 a.m. Maybe they can't. Maybe 4 a.m. too early. But how do you focus on sort of a leader's morning routine and focusing on the morning?

I mean, it's more and more people are tacking that way. The world said I travel in. So I think it's gaining traction. But it's just about asking thoughtful questions that allow them to get to that logical conclusion on their own. Like, what do you think is gonna make you the most effective leader for the people that you lead? And they start going down there and I go,

well, how do you ensure that when you hit work first thing in the morning, you are absolutely ready. And inevitably asking those really thoughtful questions generally leads to that self-realization that I gotta change my rhythm, my daily rhythm to be as effective as possible. And, you know, I mean, this is just the model that I use. I mean, I think I'm careful to make sure

that people have a system and try not to force my system on them, as long as they're executing to their maximum potential, which is what I'm always striving for in the cultures that I try to build. I think any system is better than not. For young folks, it's a lot of times they just need a little bit of guidance.

Yeah, no, I think it's like, when do you do your best work? And how do you design your day around that? And I think what are the chances that you do your best work at four in the afternoon after, you know, you put up with a bunch of crap and phone calls and errands and stuff in the beginning of the day. I mean, I'm so serious about it that I block when I get to work at the Pentagon,

I block the first hour, just don't put any meetings in there. It's just thinking space, either read emails or read something. And then I literally do the same thing at the end of the day. And because I know I'm very self-aware that I will not be my best at the end of the day.

If I've been scheduled back to back, which happens a fair amount, I'm smoked at the end of the day. I'm not gonna make great decisions. I'm not gonna be as thoughtful as I probably need to be on these very complex matters that come into things. And so I just I just make a decision proactively back to the proactive versus reactive. I make a decision such that I can control my counter and I can't always but that I'm going to block that time.

One of the questions I see here is actually from a deployed battalion commander and he's talking about how, how do you deal with sort of gossip or rumors or I guess just, you know, the, the stuff that, that people talk about at work or disagreements or resentments, you know, the sort of negative stuff that a leader has to both be above, but also deal with because it can be cultural cancer. Yeah, totally. And that's a great question. So thank you for whomever's deployed. Thank you for your service and for the

service of your family for being overseas and taking care of our nation's business or our allies and partners business over there. Certainly in a military context as a battalion commander, we are blessed to have a wing person, a command sergeant major who is a senior enlisted leader, who's our wingman as a commander and whose job is to understand the sort of subtleties, tenor tone and direction of where the entire battalion is going.

And when the CSM, the command sergeant major comes and says, hey, we've got these rumors and things like that, my approach has always been to not get buried down into the each's and others, but to have a sense of when there's a lack of understanding of what's happening or where we're going. And I think as we have younger and younger soldiers, sailors, airmen, Marines, guardians, I can't forget them now and Coast Guard folks. Wait, is that the Space Force? That's the Space Force, yes. Space Force guardians. So you know, now now I hooked you up. I think you have to get a sense of when it's time to get it all hands together and I did this in the private sector too when we did some layoffs or we

had things like that which are very difficult. It's always better to sort of get at that and get clarity out there and be ready to answer those questions that come back to you, but to alleviate that distance between where you're trying to go as a leader and where the organization thinks they're going. And so I think clear communication is important. There'll always be, especially in the military, there'll always be a little bit of rumor going on. You're never gonna fight that.

I think what you have to do is rely on your subordinate leaders, those leaders underneath you to help you understand when it's time you got to get everybody together. And I think you want to lean on to your company commanders and platoon lieutenants and PLs out there to get that culture right. When I start hearing a lot of rumors,

I start hearing jitteriness in the system, that tells me that maybe we're not talking about culture enough and we need to turn the volume up on that even more so that there's clarity all the way down the organization on what it is that we're doing. It is a great rule I heard as a writer, but I think it applies to business too, or any kind of complaint, which is like,

when someone tells you that something's wrong, like with your writing, they're always right, right? And then when someone tells you how to fix it, they're always wrong, right? So the idea being, if someone's upset, they're not wrong. They are upset. They might not be informed correctly. And so, their solution is we shouldn't be doing this. Actually, the solution is I have

to explain to you why we're doing this. Right? Exactly. So, when my editor comes to me and says paragraph three isn't working, well, actually, maybe paragraph three stays exactly the same, but I have to edit paragraph two to explain why paragraph three exists. Right? So I think thinking about it with a little bit of empathy and going, look, I'm not gonna invalidate your feelings, your feelings, your gripe is your gripe,

but I can do a better job explaining to you why that's incorrect or not incorrect, but why that needs to be seen in a larger context. And I think we have to be authentically open to that feedback, right? Because if we're so egotistical and our ego is creating barriers to that receptivity, man, we're gonna jack that up

and we're gonna be all hands up and we're gonna miss that opportunity to realize that perceptions are reality and especially in complex organizations or complex situations or even one-on-one human-to-human interaction, perceptions are reality. We just got to be sort of checking our ego at the door and it's about what's right, not who's right. And if you just keep staying on that over and over and over again,

I think you find that you start to sort of figure it out with big asterisks next to it that you always need to be going to school. Well, let's talk about the opposite of gripes and complaints and gossip. Let's talk about praise, because I think, you know, there's this perception that the stoic is like sort of emotionless, that the stoic is so strict with themselves,

they demand everyone else be strict. But to me, that's a recipe for being a bad leader. So how have you thought about praise, both receiving praise, but I think more importantly, giving praise as a leader to keep people motivated and committed to the mission. Well, I think we're all humans and praise and feedback balanced with each other are really important components

of good leadership. I've always thought of the appropriate way is to praise in public and critique in private. And I'm quick to let people know how great of a job that they're doing. But I also try to be a little bit thoughtful about how much volume there is on that. Right. And I not because I mean, if they're doing a great job, I let them know that for sure. But my point is that that I want to create, at least in the military context, I want to create leaders that that sort of have this stability to them. I one of the things that I talk about is stay frosty. When I'm talking to leaders who are going to combat

or who are gonna be in combat, I talk about let's keep our cool, let's stay frosty, right? In that context. And so, when I want that praise to be deliberate, I want it to be intentional, I want it to be intentional. I want it to be thoughtful. I want it to be also somewhat measured so

that ego doesn't become an enemy down the road. Because in the end, it's about the deed, not about the glory. A true selfless leader is one who doesn't care about, a true servant leader is one who doesn't care about the glory, but cares more about the team and more about the deed. And so I hope that makes sense. I'm quick to praise, but I'm more inclined to say,

hey, man, great job, or hey, ma'am, great job with that. I'm also equally quick to debrief myself and to bring them into that debrief as well. Man, I screwed that up. I could have done that better. Here's something for you to think about too. And I think how we set that tone in feedback. Regarding your question on praise coming to me,

I think grace is an important component of leadership. And I'm always grateful and gracious about it. But I never let it go to my head. I don't mean to sort of back to your initial point about Stoics being unemotional. I'm grateful and I'm humbled by it, but it's not about me. I really believe as a servant leader that any successes that I've had in my career or in my life are direct reflections of those leaders or subordinate leaders

that have invested in me. And therefore I think I owe it to them to be thoughtful in how I receive that and to reflect that back towards those subordinate leaders or other leaders or mentors that I've had. I think about that because like, let's say you're someone who is selfless and a servant leader and you're like, well, praise isn't important to me. It doesn't do anything for me. Maybe it even makes me a little uncomfortable. It can be easy to make this assumption that

other people are all wired the same way, right? And you realize, oh, no, like, they need to be recognized, right? They need us. And I think understanding that it's called self-discipline, not the other way around. Like the standard you hold yourself to, the Stoics say, is not fair or reasonable or a good idea to just assume other people are on the same wavelength, the same priorities. That's where I got to be really in tune with the queue and I got to really read humans well and the limbic brain is such a gift in terms of understanding human dynamics and body language and stuff like that. And each individual, each of us is so unique that you have to take the time as a leader

to get to know how folks work. And yeah, what motivates this person versus that person? Somebody's about responsibility and recognition. Somebody's about money. Somebody's about solving good problems. And you know, some people just shouldn't be on the team and you got to figure that out. Absolutely, Yeah.

Let me see if there's any last question, but this has been absolutely amazing. Oh, I guess the last question is, so talking about routine, because I think it's really powerful, big part of the stoic mindset and certainly though something I was thinking about the last two weeks while I was on the road. How do you think about routine and good habits when you're deployed, when your schedule is not under your control the way that you might it might be when you're at home or you're at the office? I mean it's a great question and thanks Ryan. I appreciate I can see the chat there and on the margins. I think it's about being committed to finding a way and a rhythm that works for you. And it won't look perfect. And it may take some time to stabilize. But you know, when you're,

when you're overseas or on a deployment or on a work trip or whatever, I think you need to thoughtfully sit down. I do this even before I go on the trip. Where is there a gym? What do I think these days are going to be like? And I try to get ahead of this, so that when I land in whatever place I'm going to be at, I'm set up for success right off the bat, and I look forward to it. And I do the same thing with my team. And if your schedule is moving around, I think you just got gotta stay flexible and agile and up on the balls of your feet.

But what I will tell you is, is when you master that, especially in a dynamic environment where the schedule's changing, but you find a way to get your reading in or get your workouts in, or even if they're not as effective or the same as they are when

you're at home, the fact that you've done them will bring you strength and power and comfort that you almost can't measure. I mean, you, cause you'll feel like you've accomplished something for the day. You feel like you stayed close to what, you know know is your center post of how you set up your life. And I think, you know, being agile and flexible is an important component to this, especially when you're on the road. Now, I mean, it doesn't always work, but you know, I can always find a place to work out. I can do the stairs in a hotel.

I can do it in my hotel room, my TRX, whatever. I can always find a way to make it work. Yeah, I think one of the things that I've come to think about, especially having kids or young kids sort of throw it out, it's, you know, if routine to you is the order that you do things and the place that you do things, you're very vulnerable, right? Because everything has to go right.

If you think about it instead, like these are the daily rituals that I practice. Then you can shuffle the order around. You know what I mean? It's like, Hey, I wake up early. Okay. That's more or less a new, but, but like I work out, I take a walk, I do some reading. You can shuffle those around based on the particulars of where you happen to be. Like when I travel, I run in the morning. When I'm at home, I tend to run in the afternoon because I have more freedom at home than I do on the road, right?

And I'm not worried about hotel checkout times and where am I gonna get a shower after? So I think if you can figure out, to me, obviously if your day is chaos, you gotta figure out a routine, that's step one. But once you've figured out a routine, the next level of this is that flexibility or Robert Green talks about formlessness, the flexibility to be able to make it work in any and all environments is really important.

Yeah, I'm laughing because no plan survives first contact with the enemy, Murphy, or a four and a two year old or five and three, right? So no way, no how, but good on you guys, you and your wife for trying to keep some structure going. Well, General, this was absolutely amazing. And I can't wait to see you back in Texas soon. And thank you for your service and for taking the time here to teach us about leadership. I know it made a big difference for everyone, certainly me as well, and I appreciate it. I'm

so glad we met. Yeah, same here and I'm passionately invested in this and if anybody has any follow-on questions you can find me through the Daily Stoic or on social and I'm happy to answer them. I want to thank everybody and you and your team, Ryan, for the opportunity to spend some time with you. You're the best. All right, man, talk soon. Thanks so much for listening. If you could rate this podcast and leave a review on iTunes,

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