Jocko Underground: Chat GPT VS. Jocko Willink
7 Dec 2025 · 18 min
Jocko Willink and Echo Charles test ChatGPT's take on Jocko's leadership philosophy. The AI calls him aggressive, militaristic, and simplistic. They push back: those critiques miss the nuance buried in his actual books and podcasts, not just the headlines.
Chapters
This is the Jocko Underground podcast number 91. Sitting here with Echo Charles chat GPT.
Yeah.
It'S coming. Matter of fact, you could say it's already here. So I've been playing around with Chad GPT See what the deal is. You. You've used it for something.
Yeah.
What have you used it for?
Plenty. So, actually, I found a lot of stuff. I don't want to go off on too much of a thing, but ChatGPT turns out so far, in my experience to be a, like, an assistant person who's down to do all the research you need them to do forever.
What have you researched?
The last thing I researched was actually you. I said, write a script about XYZ.
Written by Jocko Willink.
How'd it do?
Bad. Terrible.
I've tried that too. It's not. It's off.
Yeah.
It's. It ends up with a. You. You get it with a caricature. That's what you get. You get a caricature of my writing or of me. Yeah. My personality.
Yeah. It was literally. Here's the.
Put it this. Then again, I know it's just a state of, like, how it is right now. I understand that, like, literally, like next week. It could be better in theory.
It actually is better right now.
Yeah. But currently, given when I did it a few days ago, whatever, it was poor. It did a very poor job. Very poor job. It was using words that I literally witnessed. You say, I would never use that word. And it used that word.
Do you know what word it is?
Yeah.
What, Warrior. Yeah.
I mean, if you use the word.
Never used, but there's a very specific time for that.
Yeah. And that's what I mean.
When you say often used word.
Yeah. Like you. I forget the exact context you said it, but it was. Under certain circumstances, you would say, I would never use the word warrior. Yeah, for like, for that.
For that more than once, by the way. Well, I was playing with chat GPT, so I asked it. I asked ChatGPT, what are some flaws from Jocko Willink's principles?
Pretty straightforward. It does a pretty good job. It does, like a 90% job. But here's the problem. The 10% is, like, real critical. It misses. It's like saying, hey, 90% of the ingredients for your.
Steak were correct. You know, butter, salt, pepper, steak. But the part that the ingredient misses is steak.
It landed on me as a very generic result, like, a very generic.
Like, response to your. Your prompts.
So. So I asked at this prompt, what are some flaws from Jocko Willink's principles. And it said this. Jocko Willink is a former Navy SEAL author and motivational speaker, known for his disciplined and no nonsense approach to leadership and personal development.
While he has a large following and is respected by many, there are and a few criticisms associated with him. Number one, it says and it gives bullet. That chat GPT really likes bullet points and lists. It says the first one, it says aggressive and militaristic approach. Some critics argue that Willink's leadership philosophy and communication style can be overly aggressive or militaristic. His emphasis on extreme ownership and discipline may not resonate with everyone as it can be perceived as rigid or unyielding in certain contexts.
So I actually agree with that, that that perception because what does it call says.
Critics? Well actually, I guess this is what's my fault. It's my fault because that's kind of what I look like. You know what I mean? Like I look like that I look like aggressive and militaristic. Anybody that spends any time actually going into the principles themselves will realize that it's the oppos. Rigid, in fact, open. Keeping an open mind is one of the key components. Humility is one of the key components. Listening to what other people have to say, all these things are key components. You've heard me talk about this stuff for years. So rigid and unyielding are actually the opposite of the way I have always led.
Now I get where it comes from because I also wrote a book called Discipline Equals Freedom. So they take that one thing and extrapolate it out to be an unyielding form. I mean anybody. Well, I was going to say anybody that's ever worked for me. I wouldn't, I don't know if you work for me, but you've definitely worked with me for how long? Seven years.
Seven years.
How, how, how rigid and unyielding would you say my leadership style is?
Not rigid and not unyielding. I'll tell you.
So there you go. So out of the gate, what would you give them for a grade on that, on that statement?
What? It's hard to determine what they actually mean because at face value 0 or what do you say, 1 to 10?
I give him a, I give him a 1.
I would say 1.
Yeah.
And this really just reflects of like what you guys talk about where you're like default aggressive, right? That's literally saying you have a shirt about it. Default aggressive. So ChatGPT is going to pick that up and be like, well, some people don't like that aggression. They don't like that. Whatever. But then the little caveat, which is very important, by the way, it's actually bigger than a caveat. It's like kind of the key component is aggressive isn't towards people. It's a. Towards make. It's towards making things happen. And then you're like, oh, hold. There's only one person. You got to hold yourself accountable. Not. Others are kind of. So, like, accountability. Right. Big. I'm big on accountability kind of a thing, but for myself. Exactly. Right.
So, all right, they get a 1.5. So. Well, you give them a one. We'll just give him a one. Sure. Okay, so they get a one on that one. Next one is lack of nuance. Willink's messages and advice often emphasize personal responsibility and discipline, which some critics argue can overlook systemic or external factors that influence outcomes. They argue that his approach. It's weird that there's the they. Right. Some critics quote, and they like, I've never seen this stuff before, but it captures it. They argue that his approach may not adequately address the complexities of certain situations or the impact of factors beyond an individual's control. Again, I think all this stuff is. Is my fault, because the surface kind of image or the surface impression that you're gonna get from the title of the books. Right. Extreme Ownership, Discipline Equals Freedom, Leadership, Strategy, and Tactics. All those books kind of imply this sort of thing. So at a surface value, I can see where Chad GBT is gonna. Gonna miss out here, because.
Look, I've been. We've been doing a podcast. We have hundreds and hundreds and hundreds of hours talking about the nuance of leadership and how it applies to all these different situations. So. And that's critical.
So lack of nuance.
What are you giving for a grade on this one?
Can we give zeros?
Yeah, you can give us a.
Okay, I give zero. This is why. Because literally your second book is called the Dichotomy of Leadership. So it's like.
Good point. Like, hey, that's a good point.
So lack of nuance is literally, like, against. If someone's like, there's no nuance. That's literally the opposite of what you're saying.
Yeah, that's interesting. I mean, I'm just. I just pulled out the book Dichotomy of Leadership, and the inside flap says, dichotomy provides the crucial insight and awareness necessary for leaders to understand when to lead and when to follow, when to focus and when to detach, when to tighten the reins and when to let the team run. When to aggressively maneuver and when to be prudent. Like it's literal nuance. That's what it's about. The only I can't. For me, giving them a zero would mean there's no basis in what they're saying. I have to give ChatGPT at least the credit of understanding what exists in some way. I'll give them a one. Okay, can we round it up to a one?
You make a good point with like zero basis. So like basically you got what is chatgpt hanging on to to result in this answer or what? They latch onto it. Latch onto. Maybe it is hundred percent on you kind of a thing, right? Where it's like, yes.
Which is what's interesting about that is when it talks about. They argue that his approach may not adequately address the complexities of certain situations or the impact of factors beyond an individual's control. So one of the earliest questions I got asked about this topic was someone said, hey, you know, my daughter has terminal cancer. How do I take ownership of that? And I said, hey, you can't take ownership of that. What you can take ownership of is how you respond to it. And there you go. So this is actually addressing what is in this. And it's in. I've said that a thousand times, written it, so I'll give them a one that they knew that it's a topic, but that's about it. Next up, simplistic solutions. Some detractors argue that willing solutions and strategies may oversimplify complex problems. That's the point, by the way. While his emphasis on taking ownership and developing discipline. It's obviously this thing is everything talks about responsibility and discipline and ownership, which is kind of like me, I guess. Also it's kind of getting at least a 1. Developing discipline can be valuable. Critics contend that they may not address the root causes of issues or consider the broader context in which they arise.
So oversimplifying. Maybe you're just, okay, this is one of those things where again wrote a book called Leadership Strategy and Tactics. We talk all the time about the fact that you can't just win the tactical battle that's right in front of you. You need to find out the long term solution. You need to find out where the problem is coming from. That's where you need to focus your efforts. I'm giving this A1.
Yeah, I'm assuming I understand what ChatGPT is talking about, but I actually will give it a. What do you say, one to ten?
Yeah, one to ten.
I'll give it a five.
Five. Okay, how come you're giving a five?
Because, and this is just hanging on to that idea of oversimplifying it because sometimes this is less about your philosophy though. This is more about you as a human, like actual existing human being where certain things I think you overlook as being like normal things. You overlook it like just cuz you're you and you're like, oh dang, you probably never really thought about that, that.
Certain things that much I bet that you're just wrong.
Maybe, maybe that's why. Let me give you the example.
The example is how do I get out of bed in the morning, right? This is what you're thinking, how do I get out of bed in the morning? Oh, you want to get out of the bed in the morning, set your alarm clock. When it goes off, get out of bed, period.
That's the right answer, dude. Yeah, I know you can say that there's a bunch of little mitigating circumstances, but the fact of the matter is, if you want to get out of bed in the morning, set your alarm, get out of bed in the morning. Yeah, well, your, your five just went back down to a one. You're actually wrong still at five.
In fact, you're actually wrong 5.5 right now here. Because this is, this is why. So here's the analogy where like, it's like if, if two people were yelling in your ear, right? Yelling in your ear, and you just said, yeah, just ignore. Where it's like, cool, yes, in theory, you're in a vacuum. Sure, someone could find it, you could probably ignore them, but. But the normal person, the norm, they can't ignore them. Like it's. You can't ignore them. It's too loud, it's too close to your ear. You can feel the warmth of their breath. Like there's so much, so many things that I think, anyway, I don't know, I can't read your mind, but there's certain things that affect certain people in certain ways that don't affect you in certain ways. And I feel like.
So I'm not human now.
I feel like false dichotomy. I feel like you just assume. Assume a lot of the time, not all the time, but maybe more times than you realize that certain things are literally like normal, this is normal thing for everybody.
I think I got asked this on Twitter, maybe I'm almost positive I asked this on Twitter and I responded, the question was like, hey, what do you do when you're. Because you know how a lot of times when I'm Doing Twitter, I'm traveling. And so someone wrote, like, hey, what do you do when you're on a flight and the person behind you. It keeps kicking your chair? Or the. There's a baby behind you screaming and hitting your chair while you're on the flight. What do you do? And I wrote. Right. I wrote. I write three chapters for my next book. Like, this is no factor to me. Like, literally no factor. So when you talk about people screaming in your ears and what. There's some people that have some kind of a medical trigger that goes off when they get yelled at. No, it's not true. Like, you're not. You're not.
You're not.
That's not. That's not true.
If.
If Captain Plum can be in a prison cell in Hanoi and. And take ownership of being annoyed with his cellmates, I think you can take a little ownership if someone's annoying you by being loud.
Right? Yeah. And see, now you're going, like, with these kind of absolutes where you take this extreme situation, like, probably one of the most extreme situations ever. Can you compare that to everyday person and be like, look, like, what the hell? You know?
But, but, but isn't there some validity to that?
Yeah, but.
Because if a human being can be locked in a prison cell in a prisoner of war camp and decide that he's going to take ownership of things that are really, truly bothering him.
Yeah.
In an area where he's trapped.
Yeah.
Then someone's talking on a plane or yelling on a plane, and you're going to let that drive you crazy, where you want to lash out. Like, is that where we're at?
So in real life. Yes, because that extreme situation does. That's a very extreme situation. And in certain situations. Yeah. A baby crying is. I'm probably not even hear that in certain situations, especially the more extreme the situation. So, again, like you. It comes down to simplifying it like that, where it's like you're taking something like literally a million steps down the road, and you're saying that's the same as step number one and two. It's different.
It's.
There's more to it than that, is what I'm saying. And I'm not saying it's bad or good. And in fact, in theory, that's how you operate. That's how everyone operates. That's. That's the whole point. There's so much.
That's the mistake. The mistake is saying, instead of saying, ho, I want to write a book, people say, oh, yeah, how do I Write a book. I say write a thousand words a day. It takes one hour. Find that. One hour. Write a thousand words a day. People act like that's the craziest thing they've ever heard. People want to get up in the morning. Oh, you set your alarm clock. Oh, people want to. You know, they're having trouble working out every day. Cool. You know what I do? Go work out every day.
Yeah.
And I mean, these are not. I think. I think you're actually. You actually could be wrong here. You're overcomplicating things, because that's human nature. That's why simplicity is such a powerful tool.
Yes, yes. And I agree with that.
I mean, sure, could we sit here and say there's all these different mitigating circumstances that unfold when someone. The alarm clock goes off, and they were up late last night and their circadian rhythms off, and they want to wake up their wife, and they actually were feeling a little bit sniffly in the. When they. Their nose is a little bunged up as they slept. And there's, like, a bunch of things. Right. A bunch of reasons. And probably you need more rest and.
Yeah, yeah.
You know, the. The podcast told me that sleep was the most important thing for longevity. Like, all these things.
Right?
There's all these things. Sure.
Yeah.
They can all. You can all. Keep you in bed.
Yeah.
Pillow feels good.
Yeah, yeah, I get it.
Warm blanket feels good.
Right. And it's less about any specific thing. What I'm saying is you as a human being, not your. The thing is, you're right about the thing. Like I said from the bean, like, your approach to it is correct. Just a little oversimplified to a level of 5 out of 10. So I'm saying. So again, this is like you personally.
So you know what? For the sake of brevity, we're gonna go with five. We're gonna go with. With your complete. We're gonna have full credit. We're giving it five. Look, because everything's super complex.
That's not what I'm saying. That's not what I'm saying at all.
See?
See how you're oversimplifying the thing again? So you got. Look, do you know what. You know what tolerance is, right? Do you believe or do. Do you know or believe? I don't know. Maybe you don't believe this, that different people have different levels of tolerance, like, actual tolerance.
Tolerance for what?
Anything. Just anything.
Yeah, different people have different levels of tolerance.
Exactly. Right. So even just that alone would. Would make things clear. That it's not just like, hey, no, you just do it. Or a no, just ignore them. We're like, just. Just the individual nuance of tolerance, it in and of itself makes it not that simple.
The approach is the same, okay, like, hey, let's work towards this. Let's work towards that. Here's, I think, where the mistake kind of comes in real life when people will be like, hey, everyone's different. Hey, it's easier for Jocko because he has high tolerance for this stuff or whatever. Therefore, it's okay for me to slack. It's like that. When they. When they come to. When someone comes to that conclusion, and I'm not excluding myself either, when they come to that conclusion and use it as like a crutch, there's where the problems.
Well, that's definitely a problem.
So I understand the usefulness of your simplistic approach.
Okay, so that's a good point. And we'll give it a five. And for those of you that want to believe the Echo Charles system of complexity and everything's a lot harder and it makes a lot more difference. And everyone's different. There's always in Jacques, I'm some kind of a freaking robot cyborg. Over. So that is a little excerpt of what we are doing on the Jocko Underground podcast. So if you want to continue to listen to.
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