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The Daily Stoic

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

22 Jun 2026

Transcription

Transcript generated automatically by AI and may contain errors.

Chapter 1: What key Stoic virtues are introduced in this episode?

0.031 - 25.846 Ryan 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. 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.

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26.587 - 43.953 Ryan Holiday

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.

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44.453 - 65.966 Ryan Holiday

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. 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.

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66.567 - 89.586 Ryan Holiday

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.

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89.927 - 93.656 Ryan Holiday

There will be times when we have to collaborate. There will be times when we have to adjust.

Chapter 2: How does the philosophy of Stoicism relate to flexibility and firmness?

93.997 - 114.941 Ryan Holiday

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.

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114.961 - 145.839 Ryan Holiday

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. 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. I don't know if you've ever done any live shopping, but it's blowing up.

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145.919 - 155.416 Ryan Holiday

And some of the kids, I don't know if I call them kids, but some of the Gen Z kids on my staff had to tell me about it. They really love it because you can find vintage stuff and collectible stuff.

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Chapter 3: What lessons can we learn from the life of Cato?

156.097 - 178.26 Ryan Holiday

I was looking at some videos of people selling vintage band tees and records and watches. And it's real people selling. Like if you're going to an estate sale or a really cool, trendy shop, not, you know, overpriced stuff, not produced stuff. There's no ads, no marketing. And people are on there explaining their stuff, why you'd like it, what's cool about it, where they got it.

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178.661 - 197.404 Ryan Holiday

Like I love buying stuff on auctions. So I think I'm gonna like Whatnot. And I think you will too. There are people making over a million dollars a year on Whatnot. In fact, that number has doubled in the last year. Whatnot is the largest dedicated live shopping platform, whether it's beauty, collectibles, electronics, luxury fashion, even cookies.

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198.065 - 215.53 Ryan Holiday

Sellers are building real thriving businesses on Whatnot. Whatnot buyers spend more than an hour a day on the app, and they're not just browsing, they're bidding and buying and coming back. So you can go live, show off your projects and turn that into real income. People selling on Whatnot sell 10 times more than on other major marketplaces. And that's because you're not just listing products.

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215.891 - 235.839 Ryan Holiday

You're building real connections with buyers. Download the Whatnot app today and get free shipping on your first order. Just search Whatnot, W-H-A-T-N-O-T in the app store to start scoring amazing deals. You know what silently kills sales teams? The inability to see what's happening in their pipeline.

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236.32 - 242.854 Ryan Holiday

And part of the reason they can't do that is because they use software or CRM that's so complicated that people don't even log in. I do this all the time.

Chapter 4: How did Marcus Aurelius exemplify the balance of strength and flexibility?

242.874 - 262.19 Ryan Holiday

You get some tool and you're like, I'm going to use it. And then it's so complicated you don't use it. And that's where today's sponsor, Pipedrive, comes in. It's an easy, intelligent CRM loved by growing sales teams and most important, actually used by them. Pipedrive gives your team one complete trusted record of every customer and deal.

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262.631 - 285.778 Ryan Holiday

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285.758 - 314.673 Ryan Holiday

And our link gives you an exclusive 30 days free instead of the usual 14-day trial. No credit card or payment needed. Just head over to Pipedrive.com to get started. That's Pipedrive.com. You can be up and running in minutes. The 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.

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314.734 - 336.498 Ryan Holiday

Marcus 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?

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336.518 - 344.55 Ryan Holiday

Or what are you hoping it'll be like when you get it? And you'll find that at the very core of it, people want freedom. They want happiness. They want the respect of their peers.

Chapter 5: When should we bend or compromise in our lives?

345.352 - 366.324 Ryan Holiday

A Stoic 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.

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366.885 - 377.722 Ryan Holiday

Freedom, that's easy. It's in your choices, the Stoics would say. Happiness, that's easy. It's in your choices, the Stoics would say. Respect your peers. That too is in the choices you make.

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Chapter 6: What is the significance of knowing when to stand firm versus being flexible?

378.504 - 399.823 Ryan Holiday

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. What if you got another boat and another boat? You scale this operation. You can make all this money.

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399.883 - 417.578 Ryan Holiday

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. And 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?

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418.099 - 438.241 Ryan Holiday

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.

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438.261 - 456.414 Ryan Holiday

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? And 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.

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456.915 - 476.128 Ryan Holiday

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.

476.669 - 501.498 Ryan Holiday

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? It's after I become rich and successful, after I make it, after I win a Super Bowl, blah, blah, blah, blah, blah. 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.

501.518 - 520.223 Ryan Holiday

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.

520.203 - 543.387 Ryan Holiday

And 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?

543.727 - 562.107 Ryan Holiday

I feel like I have enough. I feel like there's nothing I'm really trying to prove, but I 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, doing it because I actually enjoy it. And knowing that

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