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

Summary

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The Daily Stoic Podcast

Episode Title: You Have To Be Both These Things | The Long Way Around
Date: June 22, 2026
Host: Ryan Holiday

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Episode Overview

In this episode, Ryan Holiday delves into two interconnected Stoic concepts: the balance between unwavering principle and necessary flexibility, and the folly of taking the “long way around” to fulfillment when contentment is already within reach. Drawing on historical examples like Cato and Marcus Aurelius, as well as memorable anecdotes and Stoic maxims, Holiday unpacks how wisdom lies in knowing both when to stand firm and when to adapt—and encourages listeners to embrace the idea that they are already “enough.”

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Key Discussion Points

1. On Principles, Flexibility, and Wisdom (00:00–01:47)

• Stoicism as Firmness and Discipline:
  Ryan opens by affirming the Stoic ideal of steadfastness—highlighting virtues such as courage, discipline, justice, and wisdom as “firm” qualities.
  • Quote (Ryan Holiday, 00:10):
    “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.”
• The Example of Cato:
  Using Cato as a cautionary tale, Ryan warns that absolute inflexibility—though principled—can be counterproductive, as it was to Cato’s legacy and the fate of the Roman Republic.
  • Quote (Ryan Holiday, 00:36):
    “Cato was a man of principle... but 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.”
• Learning from Marcus Aurelius:
  Marcus, in contrast, balanced conviction with pragmatic tolerance and openness to others, drawing from his teacher Apollonius the lesson that one can have both “strength and flexibility.”
  • Quote (Ryan Holiday, 00:59):
    “A man can both show strength and flexibility. What a great combination. And it’s one that we have to cultivate, too.”
• Wisdom as Knowing When to Bend:
  Wisdom is characterized not by rigid certainty, but by the discernment of when to stand firm and when to adapt.

2. Wisdom Takes Work: Applying Stoicism (01:47–02:33)

• Wisdom as Ongoing Effort:
  Ryan connects the earlier theme to his book, “Wisdom Takes Work,” asserting that wisdom is not innate but cultivated over time through practice and reflection.
  • Quote (Ryan Holiday, 01:54):
    “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.”
• Stoic Wisdom Across Time:
  He frames Stoic development as a continual process, exemplified by figures like Marcus Aurelius and Abraham Lincoln, who continually applied and refined their principles.

3. The Long Way Around (04:53–09:41)

• Chasing Goals vs. Contentment: Ryan uses Marcus Aurelius’ Meditations (12.1) to emphasize that people often pursue long, complicated paths to attain things (like happiness, respect, or freedom) that are already accessible in the present.
  • Quote (Marcus Aurelius, Ryan quoting, 04:53):
    “You could enjoy this very moment all the things you are praying to reach by taking the long way around if you’d stop depriving yourself of them.”
• The Trap of “Once I Have…”:
  Many chase career success, money, or recognition, believing happiness or peace will come after these milestones. Stoicism counters that fulfillment comes from the choices and actions within our present reach.
  • Quote (Ryan Holiday, 05:29):
    “People want freedom. They want happiness. They want the respect of their peers… 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.”
• Classic Tale of Contentment:
  Ryan recounts the oft-told story of the fisherman and the businessman (06:22–06:46), illustrating unnecessary striving for an end-state already available, linking it back to ancient sources.
• Author’s Personal Anecdote:
  He shares his experiences of envying the perceived success of others—only to find they envy his own life in turn, underscoring the lesson that “what you want, you may already have.”
  • Quote (Ryan Holiday, 07:03):
    “They invite you over to their fancy houses, and you sit there and you go, man, would it 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… I’m jealous of their life; they’re jealous of my life.”
• The “Enough” Story (Vonnegut and Heller):
  Referencing a famed conversation, Ryan reminds listeners of Heller’s wisdom:
  • Quote (Joseph Heller, as recounted by Ryan, 08:21):
    “I have something that he doesn’t have… I have enough.”
• Contentment in the Present:
  Ryan urges: seek fullness and sufficiency from within, not as a byproduct of chasing external goals.
  • Quote (Ryan Holiday, 09:32):
    “Give yourself the gift of enough, because you are enough.”

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Notable Quotes & Memorable Moments

• “A man can both show strength and flexibility.” (Ryan quoting Marcus Aurelius, 00:59)
• “Wisdom isn’t this thing that you have. It is work that you do.” (Ryan Holiday, 01:54)
• “You could enjoy this very moment all the things you are praying to reach by taking the long way around if you’d stop depriving yourself of them.” (Marcus Aurelius via Ryan, 04:53)
• “I have enough.” — Joseph Heller (as recounted by Ryan Holiday, 08:21)
• “Give yourself the gift of enough, because you are enough.” (Ryan Holiday, 09:32)

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Important Timestamps

• 00:00 — Episode theme: Balancing firmness with flexibility, principles vs. collaboration
• 00:36 — The life and example of Cato
• 00:59 — Lessons from Marcus Aurelius
• 01:54 — Wisdom as daily work
• 04:53 — The “long way around” to happiness and contentment
• 06:22 — Fisherman and businessman story illustration
• 07:02 — Personal anecdote: Success, envy, and mutual longing
• 08:21 — The “enough” story (Vonnegut and Heller)
• 09:32 — Ryan’s closing encouragement: “Give yourself the gift of enough”

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Final Takeaway

Ryan Holiday’s message in this episode is a dual reminder: real wisdom is knowing when to combine steadfastness with adaptability, and real contentment is available in the present—not at the end of some distant, complicated journey. Through Stoic philosophy and personal stories, listeners are encouraged to seek and practice “enoughness”—a sense of self-sufficiency and satisfaction available here and now.

Transcript

[A]

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. 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. 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. 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.

[B]

It's available everywhere.

[A]

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. 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, It all comes down to hiring. You gotta find the right people for your team and you gotta bring them on board and you gotta onboard them quickly. You know, just throwing up a job posting and hoping you get lucky.

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[A]

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[B]

The long way around you could enjoy this very moment all the things you are praying to reach by taking the long way around if you'd stop depriving yourself of them. 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? Or what are you hoping it'll be like when you get it? And you'll find that at the very

[A]

core of it, people want freedom.

[B]

They want happiness. They want the respect of their peers. 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. 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. 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 fisherman in Thailand or something. And the Western businessman sees him and

[A]

he says, oh, you've got this little boat.

[B]

Well, what if you got another boat and another boat? You scaled 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. 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?

[A]

Why?

[B]

Why? Well, at the end of it, you can live in peace. Although he lives in peace now. I've experienced my. 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.

[A]

They play professional sports.

[B]

They have huge audiences, or they've made all this money, they have all this stuff, and you catch yourself being a little jealous, and they invite you over to their fancy houses, and you sit there and you go, man, would it 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? And 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. 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. 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. 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. I feel like I have enough. I feel like there's nothing I'm really trying to prove, but I still doing interesting things, and 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 of doing it because I actually enjoy it. And 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.

[C]

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