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The Daily Stoic

22 Jun 2026 · 7m · 2 chapters

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You Have To Be Both These Things | The Long Way Around

In short

Stoic flexibility vs rigid principle, and the idea that freedom, happiness, and respect are already available through present choices rather than “the long way around.”

Guest backgrounds

No guests are mentioned; this is a solo Daily Stoic episode by Ryan Holiday.

Key claims

Cato exemplifies strong principles without compromise, which made him difficult and contributed to failing to preserve the Roman Republic. Marcus Aurelius combined convictions with pragmatic flexibility learned from Apollonius (“strength and flexibility”). Wisdom is knowing when to stand firm and when to bend. People chase distant goals (freedom, happiness, respect) but those are accessible now through choices; “enough” prevents endless striving.

Notable examples

Cato and Marcus Aurelius; a “fishermen in Thailand” scaling story; Mark Aurelius’ Meditations 12.1; Kurt Vonnegut teasing Joseph Heller at a party—Heller says he has “enough.”

Written by AI. May contain mistakes.

Chapters

0:15

The Balance of Firmness and Flexibility

Discussing the importance of balancing principles with flexibility through the examples of Cato and Marcus Aurelius.

“You have your principles, you have your ways, you made your decision, you set the rules.”
4:45

The Long Way Around to Happiness

Exploring how people complicate their pursuit of happiness and freedom, emphasizing that these can be achieved through choices.

“You could enjoy this very moment, all the things you're praying to reach by taking the long way around, if you'd stop depriving yourself of them.”
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Transcript

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0:00Ryan Holiday: Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

0:14Ryan Holiday: You have to be both these things. You have your principles, you have your ways, you made your decision, you set the rules. This is what you do, this is what you think Stoicism is. And it is, no question, it is a philosophy of firmness, of unwavering commitment, of steadfastness and strictness. But there is a risk to that, as we see in the life of Cato, which I talk about in Lives of the Stoics. Cato was a man of principle. He was a man of courage and conviction. He was also incredibly difficult to deal with and ultimately fell short of preserving the Roman Republic in part because he lacked the ability to compromise or collaborate.

0:53Ryan Holiday: He was lowercase conservative, meaning that he tried always to keep things as they were, which made it hard for him to accept things that were new or different. Marcus Aurelius seems to have learned from this. He had convictions and principles. He was unyielding with himself. Yet he also had a pragmatic streak. He was tolerant of others. He met people where they were. He said that he learned from his teacher Apollonius that a man can both show strength and flexibility. What a great combination. And it's one that we have to cultivate too. There will be times when we have to bend. There will be times when we have to collaborate.

1:31Ryan Holiday: There will be times when we have to adjust. Times when we have to meet someone where they are. And what wisdom is ultimately is knowing when to stand firm and when to be flexible. That's obviously something we talk a lot about in Wisdom Takes Work, which you can grab now. It's available everywhere. We've got signed copies at the Painted Porch or in the Daily Stoic store. Wisdom Takes Work is that wisdom isn't this thing that you have. It is work that you do. It is a timeless path that we are all trying to walk. One that Marcus walked, one that Lincoln walked, one that Cato did despite his shortcomings.

2:06Ryan Holiday: And I think you'll really like it. You can grab Wisdom Takes Work, Learn, Apply, Repeat at the Painted Porch or anywhere books are sold.

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4:49The long way around. You could enjoy this very moment, all the things you're praying to reach by taking the long way around, if you'd stop depriving yourself of them. Mark Aurelius' Meditations 12.1. Ask most people what they're working towards and you'll get an answer. I'm trying to become insert professional or they'll tell you they're trying to get appointed to some impressive committee or position to become a millionaire, to get discovered, to become famous, whatever. If you ask them a couple more questions such as, why are you doing that? Or what are you hoping it'll be like when you get it?

5:25And you'll find that at the very core of it, people want freedom. They want happiness. They want the respect of their peers. Astellic looks at this and shakes their head at the immense effort and expense we put into chasing things that are simple and straightforward to acquire. It's as if we'd prefer to spend years building a complicated Rube Goldberg machine instead of just reaching out and picking up what we want. It's like looking all over for your sunglasses and realizing they were on your head the whole time. Freedom, that's easy. It's in your choices, the Stoics would say. Happiness, that's easy.

5:58It's in your choices, the Stoics would say. Respect your peers. That too is in the choices you make. All of that is in front of you. No need to take the long way to get there. It's actually like a viral email chain. You've probably seen it before about the fishermen in Thailand or something. And the Western businessman sees him and he says, oh, you've got this little boat. Well, what if you got another boat and another boat? You scale this operation. You could make all this money. And the guy says, well, then what? And he's like, well, then you could retire and live on a beach somewhere. The guy says, but that's what I do now.

6:33And actually, this story dates back to like the 14th century. It's about a king who's advised by his advisor to, you know, conquer this territory, this territory, this territory, this territory. Why, why, why? Well, at the end of it, you can live in peace, although he lives in peace now. I've experienced my own version of this as an author. It's been funny. I meet these really successful people who do the things that I sometimes wish I could do. They play professional sports. They have huge audiences, or they've made all this money. They have all this stuff. And, you know, you catch yourself being a little jealous and they invite you over to their fancy houses and you sit there and you go, man, what would be so cool to live this life?

7:14And then I find out the real reason they invited me over is that they want to learn how to write books, right? Like I'm jealous of their life. They're jealous of my life, right? And it's, I think this is what Marcus is saying is that you can have what you want right now. And more importantly, the thing that you think will bring you something, peace, contentment, happiness, whatever. It's not going to happen. It's this horizon that you never quite meet. It's always a little bit out of view. Marcus is saying that we try to get our stuff the long way, the hard way, at the end of this long war, at the end of this long journey, right?

7:51It's after I become rich and successful, after I make it, after I win the Super Bowl, bah, bah, bah, bah, bah. Then I'll feel good. Then I'll be able to spend time with my family. Then I can be at peace, whatever. And you can have that right now. I have this chapter in Stillness is the Key about Enough, but it's one of my favorite stories. Kurt Vonnegut, Joseph Heller, they're at this party, this rich person. Again, just like I was just telling you that I've experienced myself and Kurt Vonnegut is sort of teasing Joseph Heller. And he says, you know, this guy made more money than your books will ever make in your life.

8:27And Joseph Heller says, yeah, but I have something that he doesn't have. And Vonnegut says, what could that possibly be? And Joseph Heller says, I have enough. I have what I need. And that's what Marcus is saying, too. You could have it right now. It's already yours. It's already there in the things that you control. Having the other stuff is nice and you can still get it, right? I feel like I have enough. I feel like there's nothing I'm really trying to prove, but I'm still doing interesting things. I'm trying to do it from a place of enoughness and fullness, not a place of emptiness, right? Not a place of having to prove myself, of getting more and more and more, but doing it because I actually enjoy it.

9:07And knowing that if I don't finish, if I don't make it all the way there, if just the time that I spent working on it today was all I got, that was enough. That itself was enjoyable. and to me that's just a much healthier place to live and be and operate from and I hope you can give yourself that gift give yourself the gift of enough because you are enough

From the publisher

There will be times we have to bend. There will be times we have to collaborate. There will be times we have to adjust, times we have to meet someone where they are.


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