How To Actually Build Discipline - Gen. Stanley McChrystal

Gen. Stanley McChrystal is a retired four-star U. S. Army general, former commander of U. S. and NATO forces in Afghanistan, and and an author. From the battlefield to daily life, it’s the small consistent choices that win both. So how can traits like discipline, integrity, and character shape everyday success and even prepare you to lead at the highest level? Expect to learn how the General thinks about discipline and what makes discipline such a powerful predictor of personal and professional success, how to balance high standards for yourself with gratitude for what you’ve achieved, why character is so important and how Stanley defines it, how leaders balance personal ambition with the greater good, and much more… 00:00 Nearly Getting Expelled From West Point 04:19 Learning From Any Experience 12:55 Why Is Discipline So Highly Valued? 23:51 Having Both Gratitude & High Standards 34:47 Balancing Service With Personal Ambition 47:16 The Role of Conviction 51:38 The Price You Pay For Success 57:14 Where to Find Stanley - Get access to every episode 10 hours before YouTube by subscribing for free on Spotify - https://spoti.fi/2LSimPn or Apple Podcasts - https://apple.co/2MNqIgw Get my free Reading List of 100 life-changing books here - https://chriswillx.com/books/ Try my productivity energy drink Neutonic here - https://neutonic.com/modernwisdom - Get in touch in the comments below or head to... Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx Email: https://chriswillx.com/contact/

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

• 0:00Chris Williamson?

  I didn't know that you nearly got expelled from West Point.

• 0:04Speaker 01

  I did. I, uh, I had two problems my first two years at West Point. The first was I wasn't as academically prepared as some students and I didn't have good study habits. So I had a very low grade point average, but that wasn't really what threatened me. I had a discipline problem. So, starting my first summer, I got what they call a slug. And that was for disrespect toward a cadet superior. Uh, they actually called it disapprobation. I had to look at, up the word. I didn't know what it meant. And I got that. And then a few months later, I got caught drinking. Well, I didn't get caught drinking. I got caught drunk. And so I got in significant trouble for that and they put you on the area to walk punishment tours.

• 0:49Speaker 01

  You might've seen that where you walk out on this, it's a, a courtyard in the middle of the barracks. And you have your rifle and you walk back and forth for an hour at a time. And you are awarded those punishment tours in hours. So like if you get convicted of an offense, you would get a certain number of demerits, a certain number of punishment tours, and then a certain number of months of special confinement. And that meant that when you weren't walking punishment tours or in class or something like that, you were in your room. You couldn't go out. It was like being in prison. So I got my first big one. I got a three-month, uh, slug. And then I got off on a Friday. I walked my last tours on a Friday in the fall.

• 1:35Speaker 01

  And, you know, you gotta celebrate. So I actually had a date with a young Italian girl from North, uh, from New Jersey and she came up. And so on Saturday, we went to the football game. My friend and I and she and her friend. And so we go to the football game and that was great. And then the idea was they would go back to the fair hotel where they had rooms. And they would change and get ready for the formal that night. It was gonna be a formal dance. So we went up to our room theoretically to get ready, but we had more time than we needed. So we started drinking. And we started drinking one fifty-one proof rum, mixing it with some cola out of that Coke machine. And sort of the last thing I remember is getting caught again.

• 2:20Speaker 01

  Literally the night I was, you know, the day I was off my first one and I get a second one. And I'm about to get thrown out for that because I go into this commandant's board where a Colonel is the president of the board. And he was a, you know, obviously an older Vietnam veteran, real mature guy. And I thought they were going to throw me out because based upon how much the punishment would be, it would either put me over demerits and throw me out then or not. But when I walked in, he goes, I don't get it. He says, you just got off this other one and now we're about to hit you with another big slug. And as soon as he said that, I knew I wasn't going to get thrown out because he just said, you know, we're dismissing you.

• 3:05Speaker 01

  I knew I was going to get under the wire. So it was another big slug. It was another 44 hours on the area, another two months of special confinement. And so it was pretty painful, but I didn't get thrown out, which was a positive.

• 3:18Chris Williamson?

  What did you learn from that? What were the lessons that you took away?

• 3:21Speaker 01

  Well, it's interesting. In the moment, I didn't learn a lot, but over time, when I process it later, you know, I'd always wanted to be a soldier. I wasn't as interested in West Point as I was to be a soldier. So I had to go through West Point to be my father because my father was my hero. He was a combat veteran, Korean, Vietnam, was still on active duty at the time. And so I was trying to be him. And I put it all at risk. I literally put, you know, it's a great story now when I go up and I've spoken at Westport a few times. Here I am, retired four-star general. I can joke about how many punishments I had and how close I was to get thrown out. But if I'd gotten thrown out, it wouldn't be a funny story.

• 4:05Speaker 01

  It would be something I probably didn't mention. It would have been an opportunity loss. So, you know, maybe late in life, I learned if there are things that really matter, value them.

• 4:17Chris Williamson?

  That's interesting. Yeah, I've been thinking a lot, reflecting a lot on our ability or inability to learn particular lessons. And it is strange how, what we would like in the perfect world of sort of philosophical equanimity would be regardless of the outcome, I am able to take the virtuous and useful truths away from any situation. But you're so right to say that had you have been thrown out, it would have completely colored the entirety of that, despite the fact that everything up until the point of which you were thrown out was exactly the same, right?

• 4:56Chris Williamson?

  So I think it's maybe in some ways reassuring for people who have gone through a hard time and sort of fell flat on their face. So they struck out in one form or another and they go, God, why is this so hard for me to alchemize into a, well, I'm glad that that happened. It's like, well, because what we want as humans is a redemption story. We want to feel like a difficult thing happened, sure. Or maybe I was good and then a difficult thing happened, but I bounced back and I got myself to a place I wanted to be. And it explains two things. It explains first off, why it was difficult for you to learn the lessons during it because you're still in the eating shit mode. You're not in the redemption bounced back mode.

• 5:39Chris Williamson?

  And it also explains, I think, why when people have had a string of either bad luck or failures that are their fault or somebody else's fault or whatever, that they can start to feel like the world is against them in a manner which is really truly unfair because they think, God, I'm not even learning anything. I haven't even alchemized or integrated anything from this because the, people say that first impressions last, but I really think that last impressions last even more. There's sort of, there's even an idea which you're probably familiar with from psychology called the peak end rule, which suggests that the most emotionally intense and final moment of any experience or the most salient are the ones that seem to sit in memory. So if you were to have a colonoscopy, which was what the study was originally done, I

• 6:24Chris Williamson?

  think it was maybe a colonoscopy or an endoscopy. The most painful point and the end are the two that sit in memory for the longest time. So interestingly, if you are getting a colonoscopy or an endoscopy and they leave the device inside of you for additional period of time, but at a much lower pain threshold, even though the overall amount of pain and discomfort has increased because the duration is longer, your recalled amount of pain is less because you finished the end of your peak end was lower. So I think all of that together just explains why during an uncomfortable experience, it can be hard to have the perspective, the 30,000 foot

• 7:05Chris Williamson?

  view. I see how this is a part of my bigger picture. And also why if you have had a string of bad, a bad run, bad series of luck moments, that it's difficult to work out how you should be grateful for it.

• 7:21Speaker 01

  Yeah, my, my experience at West Point was much like a colonoscopy. So it's nice of you to remind me.

• 7:33Chris Williamson?

  Yeah, I, I imagine so. Was that, did you get any closer or did you glance off the bottom of discipline many more times in your career?

• 7:46Speaker 01

  No, really, my first two years at West Point, then a couple of things happened. One is I probably started mature a bit. Second is I met, I met a girl I'd now been married to for 48 years. And so she sort of helped, she gave me a reason to, to sort of straighten up. And then I had a new tactical officer come in. And when he came in, he had this first meeting with me at the beginning of junior year. And I had just had this two horrific years and I was almost like a felon. And so we had this initial interview and he says, you know, I think you're going to be a great army officer.

• 8:22Speaker 01

  And I, I wanted to lean over and see if he was looking at the right file. And I said, you know, you know who you're talking to? And he says, the stuff that you're not good at is here at West Point. It doesn't matter. He was a special forces officer not long back from Vietnam and he goes, this stuff doesn't matter. We've just got to get you through this and in the army. And what I see in your file is I think you're going to be a great soldier. Now, whether he really believed that or not, it had an amazing effect on me. Because here's a guy I respected highly, who said I would. And it started to convince me, yeah, I can do this. All I've got to do is make it through this gauntlet. And then I'll get to the army, which will be better suited for what I like.

• 9:06Chris Williamson?

  So I'm going to draw an analogy between the sport of CrossFit and your challenge here. But stay, stay with me. I promise I'm going to bring this one back. So in CrossFit, if you want to make it to the Games, which is their annual elite, you probably know this, annual sort of elite competition, you need to go through the open, some form of regionals or sectionals competition. And then typically you make it to the Games after that. Maybe there's another one in between. And the way that the three different competitions are structured is that they have highest work capacity

• 9:45Chris Williamson?

  and intensity in the beginning, but lowest load, because it needs to be millions of people do these workouts. So they can't load them at, at numbers that only 1% of CrossFitters can do, or else everyone feels like a failure. So at the very, very beginning, you end up with this quite sort of broad, but very intense workout. Less technical perhaps. And then you get to the middle and there's some slightly more technical, slightly heavier weights that steps up. And then you get to the very end and then you're talking about. Paddle boarding, you're talking about Olympic pool, swimming, open water, swimming, biking, rope climbs, very high rope climbs, complex objects, flipping stuff. My point being, a lot of the time, you can be an athlete that would be phenomenal in regionals

• 10:28Chris Williamson?

  or the games, but you have to make it through the open. And if you say, hey, you know, I'm just really strong, man, like I'd crush it in the games. It's like, dude, it doesn't matter how well you do in the games. You have to get there. You can tell me all you want about how your deadlift's stronger and you'd be able to flip that object and I'm great on a paddleboard or in an Olympic pool. Awesome, but you sucked at the first workout that everybody on the planet did. So what do you expect? And I think remembering as well, the steps that you've got to go through, you've got to earn your stripes and sometimes that you actually have to earn your stripes at something which to you is more difficult before you can get onto something which to you is going to be more applicable.

• 11:10Speaker 01

  You saw that very much in the army, particularly in elite units, because the things that you go through in your initial entry training and then all the basic years are pretty mundane and everybody can do it. But you've got, they've got to be patient enough, consistent enough and stick with it to get to that. You can often see that talent in them down low, but then you also see sometimes if they don't have the persistence, the discipline to go through it, that also shows up later. Because it's clear that they haven't valued the in-state highly enough, kind of like I was guilty of.

• 11:47Chris Williamson?

  How do you come to think about discipline after all this time?

• 11:50Speaker 01

  I think discipline is the most important thing we have. And when I talk about that, I start with self-discipline. Self-discipline is the ability to get yourself to do those things which you believe you should do and you decide to do. I think it's the gap between. Really good leaders and sort of everybody else. And I think it shows up in every part of life. If you show me somebody whose personal life is a shambles, their finances, their love life, their this, I have a very difficult time wanting to trust my fate to them. Because I believe they just don't have the discipline to take care of the basics well, even though they may not think they're as important as other things.

• 12:33Speaker 01

  And most of us know how to be good leaders if we talk about leadership. You know, there's plenty of books, there's plenty of checklist. The answer is there. The difference is who's willing to do it, particularly when they're tired or they're impatient or they're angry. Who's willing to actually lead the way they know they should?

• 12:54Chris Williamson?

  What, what do you think makes discipline such a powerful predictor of, of success? Like what, why is it such a selection criteria? Is it that most people don't have it? I, it seems to be something that's accessible to almost anybody. Discipline is essentially just consistency, right? So why is it such a, an outlier predictor or an outlier trait?

• 13:20Speaker 01

  Yeah, I think it is because for one, we haven't inculcated it in society broadly enough. I think you don't just, you're not just born with discipline. I think part of it is learned through experiences. A lot of people look at the special operating forces, Navy SEALs, Army Delta Force, Army Rangers, and they see these people who are superhuman physically and brilliant. They can do all of these things and that's not true at all. In every one of those organizations, the actual standards to get in are not very high. The selection processes, like for the Army Rangers, a nine week school is torturous. I mean, it's just the most annoying nine weeks of your life.

• 14:05Speaker 01

  And less than half of all people who start, complete and get their Ranger tab. But the vast majority quit, only a very small number fail.

• 14:14Chris Williamson?

  Have you got any idea what the percentage is typically?

• 14:17Speaker 01

  I, I would say that probably about forty percent or thirty five percent get the tab and maybe five percent flunk. The rest all self-select out. The only thing different is who decides not to quit. And that's the same with the seals, that's the same with others. So that's what they test for, the, the selection processes are designed to see who's persistent. Who won't quit because that actually shows up later. In times when you really need it, again, you don't need brilliant people. You need people who commit themselves to something and then won't turn away. And that's a lot of, that's a lot of what courage is.

• 14:58Speaker 01

  Courage is, I will do something because I know I need to do it and I'm going to do it even though I'm frightened.

• 15:06Chris Williamson?

  I wonder, and I, I've been thinking about this recently. I think from the outside, some of the stuff that I've done in the few careers that I've had. Probably looks a lot like discipline and in some ways it, it'll be some discipline. But there's quite, when I reflect on it really closely, there's quite a lot of stubbornness in there. And it's sort of stubbornness masquerading as discipline or appearing as discipline. And I've sort of got it in my head at the moment that the two are pretty. If you can channel stubbornness in the right way, it gets perilously close to discipline. You know, you're talking about this, this consistency, this not giving up, so on and so forth.

• 15:45Chris Williamson?

  So, um, yeah, for the people who are stubborn, uh, in many ways, perhaps your, uh, boyfriend or girlfriend is gonna, uh. They're not going to be a huge fan of it, but I think you can channel it in a, a useful way.

• 15:59Speaker 01

  I think it's absolutely true. I think stubbornness and pride, those things interact and they do look a lot like discipline and who's to say they're not?

• 16:09Chris Williamson?

  What was that story about the standards of the US Army Rangers influencing other, the more broad military standards?

• 16:18Speaker 01

  Yeah, they, coming out of Vietnam, the US Army was a shambles. It literally had been torn to pieces, integrity, standards, everything which you would see in a good unit, you sort of didn't see in most of the US Army.

• 16:32Chris Williamson?

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• 17:13Chris Williamson?

  Shopify by going to the link in the description below and signing up for a $1 per month trial period, or by heading to Shopify.com/modernwisdom, all lowercase. That's Shopify.com/modernwisdom to upgrade your selling today. Just that, can we just linger on that for a moment? Can you just explain why was that the case? Like, tell the story of sort of what was happening to standards in Vietnam and how that was contributed to?

• 17:35Speaker 01

  Yeah, it's actually true through most wars. The US Army at the end of World War II was largely that way. There was combat experience, but discipline, interestingly enough, across the force goes down. And what happened in Vietnam was you had a drafty army, so you have people cycling through, you have attrition of non-commissioned officers and officers, so the level of professionalism is going down. You had integrity problems, you had standards problems because even though we had a draft as they were trying to enlist people, they started lowering the standards to bring them in. So by 1973 or 1974, the US Army was a shadow of what it had been in 1965, for example,

• 18:19Speaker 01

  just eight years later. And so, coming out of the war, the process of rebuilding the Army had to start from the ground up. It had to start with basics, like leadership, like professionalism, increasing the quality of the people. So you might remember they increased pay rates. We went to an all volunteer army and they increased pay a lot to get standards up. They increased command tours for commanders in Vietnam. It had been six months. So that's too fast, a turnover for an organization to do well. So they increased it to two years, which got you more consistency, got you a higher level of centralized selection. So

• 19:03Speaker 01

  you're picking a smaller percentage of your more qualified people to do that.

• 19:07Chris Williamson?

  Oh, of course. Yeah, you need four times fewer members of staff to be able to make the same, the same command units work.

• 19:15Speaker 01

  That's exactly right. So in the summer of 1973, General Creighton Abrams, who was the Army Chief of Staff, he's convinced to form two Ranger battalions. Now, the battalions had been formed during the Second World War, as elite raiding battalions. Then they'd been disbanded near the end of the war. They'd been brought back in different manifestations for Korea and Vietnam, but not as battalions. But in the summer of 73, he decides to form two battalions and sort of the cover story that a lot of people wanted to believe is he was forming these two strike battalions. But what he was really doing was forming two battalions where he could bring the best people he had together and raise the standards to what the standards ought to be across the Army.

• 20:00Speaker 01

  And he wrote this wonderful, well, he actually, somebody else wrote it and they got General Abrams to sign it. A, it's called Abrams Charter. And it basically says, "The battalion will be the best with its hands and weapons than anyone. Wherever it goes, it must be apparent it's the best. And if it's formed a brigands, it will be disbanded." So kind of warning. So they formed the first battalion in the summer seventy-three and the second battalion just months later. And they do exactly that. They take the standards for haircut standards, for physical fitness standards, for discipline standards, and they just put them as high as they possibly can. Completely different from the rest of the army.

• 20:42Speaker 01

  And what happened was, what I think General Abrams suspected, they became this gravitational pull for the rest of the army. As the rest of the army saw them around, people first wanted to try to join the battalions, although they were difficult to get in. But it, it put other organizations under pressure to try to do things better, to be as much like the Rangers as they could. Now, the Rangers were given advantages in equipment and, and other things which made it easier, but the core of it was discipline. And so, over time, as the army started to fix some of those other problems, you started to see the haircut standards, the training standards, the physical fitness standards,

• 21:27Speaker 01

  mirroring the Rangers. In many cases, some people didn't even know they were doing it. The whole army started saying "Hua" in the nineteen eighties, nineteen nineties, but that started all in the Rangers. Where did that come from? Um, I actually don't know. There's a, there's an apocryphal story of Second Ranger Battalion on Omaha Beach, when it, that the most difficult part, and General Coda goes to the Rangers and he says, "Okay, I need people who are gonna break through. We're gonna do it." And the battalion commander answered, "Hua."

• 22:01Speaker 01

  But

• 22:01Chris Williamson?

  Oh, no way.

• 22:06Chris Williamson?

  That's so good.

• 22:07Speaker 01

  That's of course apocryphal, but it became a, it became a word first in the Rangers and then across the Army. So everybody started being in some form or fashion like the Rangers. And so the Rangers had this outsized effect. And then over time, what happened is people who left the Rangers, the officers who had served a tour or more there, went out to other jobs across the Army and again, tried to get their forces. When I was in Afghanistan, I remember a guy came to me and he showed me that of all the division commanders in the Army, the two star level commanders, like 80% of them had served in the Rangers. I mean, it was just this disproportionate representation.

• 22:52Chris Williamson?

  I like the fact that you can use the quality of the haircuts as a litmus test for whether the standards across the armed forces are working well. What is it, you know, we often hear about the difficulty of Navy SEAL selection that seems to kind of at least have captured the public's attention in a, in a way that maybe the other selection haven't. What is it about the Rangers that is preparing them in this manner? What's, what's giving them this predictive power? Is it just that they were the first movers in the seventies and the eighties? Or is there something else going on?

• 23:31Speaker 01

  They were slightly earlier. The SEALs had existed back in World War II as, as frogmen. And then they had been formed and fought in Vietnam. So they were an elite organization, but they weren't very well known. When the Army created the Rangers, it was larger. It was two full battalions initially, about 1,200 people. And it started to have a bigger effect because just scale. Rangers, the big difference was this very overt discipline. I mean, you would go to a, you'd put a Navy SEAL organization here and they got long hair and mustaches and, you know, they're kind of casual. They're great fighters, but it's, they're, they're older. They're probably 10 years older than the average Ranger. Meanwhile,

• 24:14Speaker 01

  the Rangers had what we used to call birth control haircuts because they

• 24:21Speaker 01

  And so the Rangers, you know, have to do everything to this pick a un standard. But what you're doing is you're taking young people and you are shaping them over time into being just extraordinarily disciplined. And so they're different organizations, but in many way, they're complementary in what they bring, sort of a different stage of life.

• 24:41Chris Williamson?

  Mm hmm. Uh, one thing I've got in my head more sort of from a personal development perspective than a team based perspective. One of the most common tensions that I talk about and that people who listen to the show, I think are interested in is balancing high standards for yourself with gratitude for what you've achieved. And, you know, you don't want to look back on a, a career, whether it's a career of personal growth or a career in the military or a career in a sales job, a career as a parent and as a husband or a wife, and see sort of a, a series of miserable successes

• 25:20Chris Williamson?

  where I achieved the outcome, but I sort of, I never really gave myself a moment to allow gratitude, enjoyment, pleasure, moment to rest when I go through this. And I think many people, as soon as you posit an ideal, which is your standard, you then begin to compare yourself to that ideal and inevitably you find yourself lacking. And the more of a perfectionist you are, the more obsessive you are, the more detail oriented you are, the higher that standard can be. And even as you get closer to it, you're able to sort of continue to move it away from you, which is a special type of hell. How do you come to think about balancing high standards with gratitude and enjoyment

• 26:04Chris Williamson?

  in the moment for the things that you're achieving?

• 26:06Speaker 01

  Yeah, it's a great question. I'll take it at seven angles. First, I know from the Ranger standpoint, if someone's in the Rangers, there's a price to be paid. It's a little harder than other organizations. It requires more discipline. You have to wear funny haircut, all those things, but you are very happy to be there because you are in an elite unit and you take great pride because you're around people who are equally committed. We used to say the only thing worse than being in the Rangers was not being in the Rangers. And so the greatest threat we could ever make to anybody was to what we called RFS or release them for standards, throw them out of the regiment.

• 26:45Speaker 01

  And so the the sense of satisfaction most Rangers got from that, and it even bled over into families, the spouses you would think would resent them, but they didn't. They knew their husband was part of something special. They took pride in that, but they also knew that their husband was happy. And so it was this sort of shared decision that we are going to make this commitment. Now, interestingly, it's not like some places in the surveying world where the metric is money or something where people just toil really hard to achieve something like that. This was much more team oriented. You wanted

• 27:23Speaker 01

  to succeed personally, you wanted to get promoted, but there was a sense of satisfaction just being in the organization, you know, with with around the other Ranger, just wanting to stay there. And so I think that you can get people to self actualize, even when things are not everything they'd like. They don't get as much time off as they'd like. They don't get as much time to do other things because they've judged that it's just so good. They've had the opportunity to do this that you don't mind.

• 27:58Chris Williamson?

  I like that. I I think it points to one of the weaknesses that maybe a lot of people in the modern world, especially post COVID, are feeling, which is the requirement for camaraderie in driving you and encouraging you to do difficult things that if you would, if there was only one Ranger, that one guy would really, really struggle. He's, I'm doing all of this work and I've got this stupid haircut and I've got to go through this selection. And for what? There's no shared sense of suffering or or celebration. Whereas when you do it as a team and when you're part of a wider movement and when

• 28:41Chris Williamson?

  you're able to wear something on your chest that sort of says who you are, and you know that that means more than just the the words that are there. And I wonder whether a lot of people who like the sound of the solopreneur lone wolf sigma male, I'm going to lift it and do it on my own. I don't need the help of anybody. No one's around me that's supporting me thing. And maybe that's true in the beginning. It probably is. And maybe you can use that sort of resentment and that chip on your shoulder and this sense of being ostracized or left behind is real good fuel. But I get the sense that if you hold on to that fuel for too long, it it becomes inefficient. And for even longer than that, it becomes toxic. And that's certainly something I've noticed.

• 29:23Chris Williamson?

  I noticed it with training, with going to the gym, you know, for a decade and a half. I was able to go into the gym and bury myself and it it didn't really matter. I didn't care. And then the last three years or so, I just, I really, I just want to train with my friends or with my trainer, uh, who is also a friend. And I just wanted, I I can push myself really hard, but doing it on my own, I just feel like I've emptied that tank a little bit and it was good and it got me to a really good place. And I'm proud of that version of me for doing it. But I've kind of, I think, evolved beyond that or that's just not the same sort of fuel that I can use anymore. And the same thing, again, sort of speaking for myself, uh, for a long time, ran this

• 30:07Chris Williamson?

  thing, this project, just, just me and a, a video editor with a mullet and a Facebook Messenger chat and we're in different cities and then we were in different countries. And now I'm thinking, huh, like I can still do it, but I'd rather do it with a team. I'd rather do it with a squad of people that have got my back and we can high five when things go well and we can support each other when things go poorly. And, um, yeah, I, I, I wonder

• 30:33Chris Williamson?

  whether the sort of pedestalization of the lone wolf person going and doing it on their own, uh, is maybe encouraging, uh, people to stay in that mode for too long. And what, just how important the camaraderie and the sense of teamship is.

• 30:51Speaker 01

  Yeah, without being trite, it is the journey and not the destination. When I left the service after thirty four years, a friend of mine and I co-founded a company and my motivation was just to create a team that I could be a part of. I didn't care whether we made money. I really didn't care what business we went into, but I wanted a place to go. I wanted a jersey to wear. I wanted comrades because I realized that that was most important to me. That still is, and I'm, I'm pretty self-aware about that right now. And so I think when people don't understand that and they think the goal is to be X, really the goal is life between here and there.

• 31:32Chris Williamson?

  Hmm. Yeah, that's a lovely way to put it. I mean, I, gold medalist syndrome, it, you know, the.

• 31:41Chris Williamson?

  Sure. Would it be bad or would it be painful if you worked really hard and didn't achieve the thing that you wanted to achieve? But don't pretend like working really hard and achieving the thing that you want to achieve is bliss either, because when you get to that point, you have to ask yourself, well, what the fuck do I do now? Like, that's a difficult question also. And it's even with that, there's an additional level of pain, because you're in a position that no one is going to give you sympathy for. It's a champagne problem. Oh, you reached your goals. How unfortunate for you. You became a general and you were 43, 34 years and all the rest of it. And you go, yeah, I know, I get it. But it's still an existential crisis. It's still a question of what do I do now? Who is my character? Who am I after this?

• 32:21Speaker 01

  It also touches upon, we've got an attitude by some people today that says, if you're obsessed, if you work hard, you're a sucker. You know, you are going out there and you are ruining the rest of your life. You're not getting work-life balance and all that sort of thing. And I'm just not of that view. My view is there is a certain, there's a certain purity and there's a certain satisfaction that comes with obsession. And it doesn't have to mean you're a jerk in the rest of your life. You don't have a good relationship. But it means those things you want, you're willing to try really hard for. You're willing to work really hard for. You're willing to see how good I can be at that. Because if you go 70%, you always go wonder, well, if I'd only done X. I had

• 33:05Speaker 01

  a lot of people in the army used to come to me and they'd go, you know, I thought about going in the Rangers. I was gonna, but I was doing X and, you know, I had laundry in and I'd want, you know, I'd go, you got to make the choice to do those things sometimes. Because if you don't test yourself, one, you'll never know.

• 33:25Chris Williamson?

  How'd you come to think about character? Why is it so important?

• 33:29Speaker 01

  Well, it's everything. It's the essence of who we are. At the end of the day, character and I brought it down to a mathematical equation. It's what are our convictions, the things we believe in that we've really pressure tested, and then the discipline we have to live up to it. And so I think life is a journey for character, towards character, because you are trying to find out exactly what you believe. And you are trying to develop the discipline to live to that. If you think of the Stoics, think of Marcus Aurelius, and you do things a certain way to a certain standard, simply because that's the right thing to do. And I think when you can make character in its purest sense, that's sort of what it is.

• 34:14Speaker 01

  And I think character is individually based, but it's also society. Society has a shared character, sort of the sum of all of our parts. And if we can't make those parts fit together effectively, then it doesn't work.

• 34:32Chris Williamson?

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• 35:16Chris Williamson?

  or heading to gym.sh/moderndwism and using the code MODERNDWISDOM10 at checkout. That's gym.sh/moderndwism and MODERNDWISDOM10 at checkout. Is character something you're born with? Is it something that you develop?

• 35:33Speaker 01

  I think you develop it. It is, there's certainly an argument that the level of stubbornness may come from birth, the level of parts of discipline. But I know most of the things that I do, I do because I learned to do them. Somebody, I still fold my underwear in my drawers. Everybody laughs at it, but I do. And I like that.

• 35:53Chris Williamson?

  When you say, when you say everybody laughs at it, how many people are seeing your underwear in your drawers?

• 35:59Speaker 01

  That's a great question. Hopefully not many, but those who hear, those who hear about it just sort of shake their heads.

• 36:05Chris Williamson?

  Yep.

• 36:06Speaker 01

  But, but I also get up and work out. I also eat one meal a day. And I also do some other things that I think very directly make my life better than it would be. And so, you know, they can laugh at my fixation on doing certain things to whatever standard I've set. But the reality is for the most part, that has served me well.

• 36:35Chris Williamson?

  What? I wonder whether there's a sense that

• 36:42Chris Williamson?

  leaders sort of struggle to balance a character a lot of the times, as we've mentioned, stubbornness as maybe one of the traits.

• 36:53Chris Williamson?

  A lot of the times leaders become leaders because they have personal ambition, right? They want to be the person that leads the charge. Now, they can want to do it because there is this sense of

• 37:06Chris Williamson?

  giving back of service to everybody else. But let's not pretend like there's not a sense of kind of shallow need for recognition that goes into that, like what drives somebody to be the absolute best?

• 37:22Chris Williamson?

  Rarely would it be always just unmolested desire to serve and hand out to other people. So I'm interested in how people who want to become leaders, people who want to drive forward can balance personal ambition with this sense of service and this sort of greater good and this and this giving. Because there is, it seems to me like there's a tension between these two things.

• 37:46Speaker 01

  I think there can be, but it can also be synergistic. And what by that, I think the most effective leaders I've seen are very ambitious. They are ambitious because they want to take on greater responsibilities. They want to be recognized. They want to prove to others and themselves that they can do things really well. And I think such a human trait that's not all bad. But if it's married with a personal ambition. And what that ambition can be is I want to be a person that I admire, which means I'm going to live to certain values. And many of those won't be listed by the people who watch me, but I'll know.

• 38:26Speaker 01

  I'll know how I treat people. I'll know the things I do. I'll know why I do certain things. And so if those two are complementary, if you have this tremendous pressure on yourself from yourself, then you have an ambition to try to do better. What I see is people can be not only very successful, they can be very character-driven leaders and they they draw certain lines they won't cross. Now, we all know cases where the second part, the personal lines are more flexible. And when they they run into the opportunity to do to get ahead

• 39:08Speaker 01

  or or be advantaged, they're willing to push those personal standards that they know they are violating, they're willing to push those aside. That's when we drift into something that is or less than character or bad character, but we see it way too often. And we don't call people on it enough.

• 39:31Chris Williamson?

  You've got this line, leaders must must do what their people need, not what they need. Just dig into that a little bit for me.

• 39:39Speaker 01

  Yeah, if you think about a leader, often a leader needs to stand up in front of everybody and be cheered by the troops or followed by the organization, or bark and everybody scurries around their desks, whatever it is, the leader needs to feel powerful or feel successful. And in some cases, that is performance for money or for other things. And it can quickly become about the leader and you start to view this organization as the supporting cast to your greatness. But the reality is, the leader doesn't do that much. They may be very busy, but in most organizations, the leaders aren't closest to the enemy, aren't closest to the customer, aren't closest to the client. And so what

• 40:22Speaker 01

  the leader really should be is a great enabler. The person who is doing everything they can to set those other people up to be effective. Now, that doesn't mean you're down there rubbing their bellies all the time and, you know, giving them Skittles and beer. It means that you are maybe very demanding, but you're also thinking, what do they need? Not just materially, but what do they need to want to do what it is you need them to do? How do you create, you know, shared incentives so that they want to be a part of what the leader's doing?

• 41:00Chris Williamson?

  So one of my favorite books is Endurance by Alfred Lancing about Shackleton's crossing of the Antarctic. Spoiler alert for anyone that hasn't read it, he doesn't do it. In that, one of the things that I really loved is a lot of the guys had diaries and a lot of the guys were writing in the diaries. And what you get to hear is what happened and what everybody else heard from Shackleton. But then you get to see what he wrote in his diary. And it's the first time that I saw the sort of Bruce Wayne and Batman duality of a leader in a time of real crisis, mortal peril.

• 41:41Chris Williamson?

  And, you know, in his diary, Shackleton is writing about his sort of chronic uncertainties, just swimming in self doubt and fear, and he has no idea what he's doing. And, and then you hear from all of the other men in their diaries about what they hear from Shackleton when he steps out onto the field of play, so to speak. And he's just commanding and he's got it together and he's got a plan. He knows where we're going and how it's going to work. And we're going to eat the dogs and we're going to kill the polar bears. You know, they've got everything put together. And I really looked at that as quite a formative example of the price that only leaders pay.

• 42:25Chris Williamson?

  You know, there is this sort of silent self doubt that you can't let leak out. And it is a cost. It's, oh, you want to be in charge of this thing. You want to run a business. You want to be the captain of a team. You want to build a family. Okay, well, that's great. But there are going to be certain things that you basically can't share with anybody in your organization and you need to swallow that yourself and you're going to have to deal with it and then you're going to have to go back out there. Having had those doubts, get rid of them and then convince people to go forward, even though they will have the exact doubts that you've just had to overcome yourself.

• 43:04Chris Williamson?

  And yeah, I just, I really loved that book and I loved seeing a raw expose of what it's like to not be certain, but to kind of show up and do the job in any case.

• 43:19Speaker 01

  Yeah, it, that's an amazing story. If I remember, he lost nobody.

• 43:24Chris Williamson?

  Correct.

• 43:25Speaker 01

  Which is impossible in those circumstances. I very much focus on Admiral James Stockdale's experience in the Hanoi Hilton for seven years. He was a little older than other prisoners and came with a little.

• 43:37Chris Williamson?

  Can you tell Stockdale's story for the people that don't know?

• 43:39Speaker 01

  Sure. He was a Navy aviator who was shot down in 1965 and he is a little bit older, so he had a little more education, a little more philosophy and faith. And so in captivity, what he found was this case where you have no control over your environment. You are not only being poorly treated, you're being tortured. And when you are tortured, you break. And when you break, you lose self-esteem. You are forced to make statements, things which you swore you would never do. In fact, you gave an oath to the United States government that said, if captured, I'll give my name, rank and serial number. And that's just not practical. Under torture, you give more.

• 44:22Speaker 01

  So the people who are in this situation were in this hellish, long-term captivity. And what Stockdale developed was something that came to be known as the Stockdale Paradox. And that is, you need to recognize the absolute reality of your situation. The fact that you can't control certain things, it is what it is and you can't deny that. But at the same time, in parallel, you have to hold a belief in the long-term positive outcome that you need. When I think of Shackleton, I think in his mind, he absolutely knows how bad things are. But he is communicating to the people who are there with him is that the endurance is locked

• 45:07Speaker 01

  in the ice. He communicates to them, we're gonna make it. And because of his nature, they wanna believe him. And because he sticks with it and is willing to endure difficult things with them, it increases his credibility with them. But I think that's true of leaders in business, or in education, or anything. People want to believe that you're not gonna quit, that you are basically optimistic, and that you will be there for them when they waver.

• 45:40Chris Williamson?

  What role do you think moral courage plays here?

• 45:44Speaker 01

  I think it's huge, because we think of physical courage, but moral courage is much harder, in my view. Physical courage happens in a moment, you react, typically in a moment. Moral courage typically goes over a period of time, and in most cases, you're in a position where you've got a great reason to do other than what you sort of think you ought to do. Whether you are going to lose your job, or you're gonna, or go through great embarrassment, any number of things that come. And so you've got this tremendous desire to not want to step up in that moment. And someone who's got real

• 46:26Speaker 01

  moral courage inspires everyone else. When someone stands up to the bully, when someone accepts responsibility that they probably could have sidestepped, when somebody is honest when they didn't have to be, nobody's gonna catch them. I think that that, it not only reinforces in the individual, but it's incredibly inspiring. In the quick story, in the first Gulf War, I watched my commander, then Major General Wayne Downing, and we had, I was in a special operations task force, sending commandos deep into Western Iraq

• 47:05Speaker 01

  to go find Iraqi Scud missiles. And so, these little teams were sent out there, and it was high risk, and one of our teams got in contact with the Iraqis, got a couple of guys wounded, but they were able to break contact. So they called back and they said, we want to be extracted. And General Downing knew that if he extracted that team, we wouldn't get permission from General Schwarzkopf, the four-star commander, to go back in again. He knew that the effect on our mission would be essentially to shut it down. And so he said, no. And everybody was shocked because

• 47:46Speaker 01

  if that organization had then been attacked again by the Iraqis, policed up and killed, Wayne Downing's name in American Special Operations would have had a position of ignominy, ignominy forever. He would have been blamed completely. And I don't think most of them understood that what he was really doing is looking out for the organization in the long term. And it was even harder because he wasn't on the ground with that team. He was a combat veteran of Vietnam and he'd proven his courage. But when you're not on the ground and yet you force someone else to accept danger,

• 48:25Speaker 01

  it's, it's more morally frightening because if you're there with him, you can go, hey, we're all in this together. If you're not, you're out there and of course you're open to criticism. So I, I was amazed in the moment because I was one of his ops officers and I was able to watch it up close. And that was a moment of the loneliness of command. No, nobody else wanted to understand. I don't even think after the fact, most people gave him credit for that, but I, it never left me. The difficulty of that decision.

• 48:59Chris Williamson?

  Yeah, the loneliness of command is a lovely way to put it. Something else that you spend a good bit of time talking about is conviction. What do you come to think about the role of conviction?

• 49:10Speaker 01

  Yeah, I think I define convictions as things which you believe, not those superficial things you believe. Someone tells you, you know, X and you just accept it because they told you and you don't bother to look it up and you don't care. Convictions aren't that. Convictions are those things about life, about values, that you have decided to examine and to think about and really wrap your mind around. Unfortunately, I think we don't do enough conviction now. Even in many cases, our religion is the religion our parents took us to when we were young. So we just accept it. And so, most people are the religion that they are first exposed to. They didn't do a comparative analysis and pick the best one.

• 49:54Speaker 01

  Most people are patriotic to their nation because that's where they're a citizen. Most people listen to what pundits or social media influencers or whatever. And they sort of grab these beliefs and they pass them off even to themselves as their own. And they start to believe this is this, just because it is. But when you really get a chance to reflect on something and force yourself to put some opposition, red team your own ideas and beliefs, decide why you believe that. Because convictions are things you should live for, or if necessarily be willing to die for.

• 50:36Speaker 01

  And that's the bedrock that a real character is built on. Solid convictions that you are as sure about as you can be.

• 50:47Chris Williamson?

  What did you learn from Edison? He seems to be a guy that had quite a bit of conviction.

• 50:52Speaker 01

  Thomas Edison?

• 50:53Chris Williamson?

  Yeah.

• 50:56Speaker 01

  Yeah, I mean, a strange guy. Very ambitious guy, obsessed worker. When I think of him and convictions, I think he was almost single threaded on ambition. Now, an ambition that was impressive to create. But I don't think of him as one of the moral leaders that I would use as a guidepost.

• 51:26Chris Williamson?

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• 52:10Chris Williamson?

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• 52:41Chris Williamson?

  What I like, and this, it comes back to that stubbornness thing because conviction kind of has, well, it's got many meanings, but one of them being, you could say, an unwavering commitment to the mission, right? Could be, would be one way to put it. And you're right, maybe Edison, if you're going to use him as your

• 53:03Chris Williamson?

  philosophical guidepost, might not be optimal. But if you were to think about the stubbornness and the resilience piece, I mean, how many, how many different attempts did he have at the light bulb? He's given you thousands and thousands of experiments trying to do this thing. I'm pretty sure his factory burned down at one point and him and his son were stood next to it, looking at it. And Edison just had this psychotic belief, this, you know, sort of unwavering stubbornness. And it wouldn't do to have an entire organization or country of Edison's, but it's probably pretty important to have them. It's important to have Tom Brady's, right? It's important to have them, them too. But, uh, yeah, it's, it's interesting how different people

• 53:50Chris Williamson?

  with weaknesses and strengths can end up in sort of magnificent places.

• 53:55Speaker 01

  I think if we didn't have people with obsession, we'd be a much poorer society, not just materially, but emotionally, because almost anyone that I know of that really created something special or did something hard, changed things.

• 54:12Speaker 01

  Was obsessed, Dr. Martin Luther King Jr. I mean, that was his life until he was murdered. There were, there are just a whole bunch of cases and we sort of criticize them now. We say, well, they were too obsessed. They didn't spend enough time with their kids and their dog. I get it, but we have an electric light bulb, you know?

• 54:33Chris Williamson?

  Hmm, well, look, the price that people pay to be successful is, uh, it's an interesting tension. It's an interesting question I always like to ask because

• 54:49Chris Williamson?

  in some ways it's worth it because we're, we're social creatures. We need validation. We want to conquer things. We want to achieve stuff. We want to feel, finish our lives feeling like we're validated. But on the flip side, lots of people get toward the end of their life and realize that not only did they manage to climb up a ladder that they didn't mean to, but the one that if they were given the choice, they, they end up in a place they didn't mean to get to and one that they don't like as well. And you go, the goal is to, the goal is to make sure that whatever it is that you're trying to achieve, whatever your conviction is applied to, is something that you're not going to look back on with regret.

• 55:32Chris Williamson?

  And that requires actually a degree of a, a lack of stubbornness. It, it requires a little bit of mindfulness. It requires some perspective. It means that you need to drop some of the intensity. And, uh, you know, you look at, uh, any normal bell curve of traits. And although most people would say muscularity, for instance, you say to most guys, how muscular do you want to be? More, more. The answer is there is no amount of muscularity that's too much. But if you get up to the 99.99th percentile, you're talking about dying early because mTOR is on and you're carrying a lot of weight around and stress on your organs and high blood pressure and drugs and all this sort of stuff. My point being, and the same for being undermuscled, right?

• 56:17Chris Williamson?

  There are some girls that would just like, I could be, how thin do you want to be? Thinner, thinner, thinner would be like fit into a smaller dress size, et cetera. Um, when you get toward the absolute extreme of any trait, you end up in a situation where.

• 56:34Chris Williamson?

  The outcomes you get are pretty unpredictable and you end up paying weird prices. How committed do you want to be to the cause? More, more, I want to be more committed. It's like, well, if you end up being too committed to the cause, you can never have any perspective because you never question yourself. You never actually set back and go, is this what I should be doing in my time? Is this the best way that I should be spending my time? So, yes, this is why we have a range of characters within a team, right? We don't just have one person that's copied and pasted multiple times because you would end up with an entire team of the same strengths and the same weaknesses. And the point of a team is to have lots of people with different strengths and different weaknesses.

• 57:10Speaker 01

  And it's also why you have relationships with people, with partners, spouses, different people, because in most of us, they round us out. They pull us a little bit in other directions. You know, because if we didn't have those, we would, some people would live monk-like existences focused on one thing, whatever it is. And I think other people can help you round that out just a bit.

• 57:40Chris Williamson?

  Where does humility come into play here?

• 57:43Speaker 01

  Yeah.

• 57:45Speaker 01

  I think humility is hugely important and it needs to be real. You know, people can act humble but be absolutely arrogant inside and it's sort of an act. I think you've got to be humble enough to know who you are, the opportunities, maybe the advantages that you are enjoying, all of the things that, that mean that you are not maybe as special as you might want to believe you are, and your limitations. Now, it shouldn't stop you from trying to do things. You know, just because I am humble enough to believe I'm not the best person at X doesn't mean I shouldn't try to compete.

• 58:29Speaker 01

  But you need to be realistic with people, with other people, I think humility is key because it's respect. If you have humility, you are respecting that they bring something to the table and they might be, they might bring more to it than you do. And so in an organization, having humility is respect for the organization. It's admitting that you are not putting yourself on a pedestal and saying that you are, you know, the super person and that they should bow down. You're basically saying, I'm one of you. I happen to be in this position and I will do what this position requires, but realize that it is, it's to a degree, it's role playing and they know it. And that's okay.

• 59:14Chris Williamson?

  I think this is why not taking yourself too seriously can help too. There are times to, to be serious, but yeah, if you can be a little bit playful with it, I think seriousness is, is great. And I really do applaud seriousness, seriousness about emotions, seriousness in your pursuits and trying to be the best and trying to, you know, get things done. But seriousness is also when taken to the extreme, again, the 99th percentile thing. It's a kind of brittleness as well because it doesn't allow you to insulate yourself from little challenges and insults and damage that end up coming in. And it also makes you seem way less approachable.

• 59:57Chris Williamson?

  So yeah, humility with a good dose of humor, I think is a, a nice, a nice way to offset the drive, you know, that sort of psychopathic forward motion, that unrelenting desire for more.

• 1:00:10Speaker 01

  Absolutely.

• 1:00:11Chris Williamson?

  Yeah. General Stanley McChrystal, ladies and gentlemen. It's been five years, maybe more, maybe five or six years since we last spoke. And as we said before, we've both gotten younger, which is great. So I really appreciate you. I love, I love your insights. Where should people go to want to keep up to date with everything that you're doing?

• 1:00:28Speaker 01

  Well, mcchrystalgroup.com is the organization that I'm the leader of and a part of and honored to be that. It's that team that we talked about.

• 1:00:39Chris Williamson?

  Okay. Stanley, I appreciate you. Thank you.

• 1:00:42Speaker 01

  You're kind.

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