This Is How It's Meant To Be Done | It Is Well to Be Flexible

Summary

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The Daily Stoic Podcast

Episode: "This Is How It's Meant To Be Done | It Is Well to Be Flexible"

Host: Ryan Holiday
Date: June 1, 2026

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Episode Overview

In this episode, Ryan Holiday explores two foundational Stoic ideas: how Stoicism is inherently a lived, conversational, and communal philosophy, and the critical virtue of flexibility in the face of adversity. Drawing upon historical anecdotes, quotes from Seneca, and a parable involving Abraham Lincoln, Holiday encourages listeners to embrace humility and adaptability—virtues that remain as essential today as they were in ancient times.

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Key Discussion Points & Insights

1. Stoicism: A Lived and Conversational Philosophy

• (00:00-02:17)

• Stoicism is often mistakenly viewed as a solitary, scholarly pursuit, transmitted through ancient texts.
• The original practice was deeply communal, interactive, and oral—rooted in dialogue on the Stoa Poikile (Painted Porch) in Athens.
• Figures like Zeno conversed openly with all, while Cato and Epictetus thrived on in-person philosophical exchanges rather than private writing.

Notable Quotes:

• "So much of Stoicism comes down to us in books, it's easy to assume that it's a written philosophy… but that's not how we got the philosophy itself." — Ryan Holiday (00:11)
• "Stoicism was a spoken, conversational philosophy. It's meant to be heard, meant to be talked about, meant for that back and forth." — Ryan Holiday (01:44)
• "David Mamet... says what he loves about the Stoics is that they were just porch guys, just regular people hanging out, talking about how to become the best version of themselves." — Ryan Holiday paraphrasing Mamet (00:36)

2. The Importance of Flexibility (Inspired by Seneca & Lincoln)

• (05:03-09:58)

• Episode transitions to the daily lesson: "It is well to be flexible," anchored by a reading from Seneca’s writings on adapting one’s role.
• Seneca proposes: If one avenue is closed, embrace another—even if it seems less prestigious or impactful.
• Ryan shares Abraham Lincoln’s anecdote: A man, after being denied various official positions, finally requests an old pair of trousers. Lincoln concludes, "It is well to be humble," underscoring the importance of adjusting one’s expectations and contributions.
• The Stoic response to setbacks is neither bitter resignation nor naive optimism, but productive humility: make the best of any given situation, even if that means accepting a lesser role or task.

Notable Quotes:

• “The story embodies the flexibility and the determination of Stoicism. If we can’t do this, then perhaps we can try that. And if we can’t do that, perhaps some other thing.” — Ryan Holiday (06:17)
• “You find your role, you’re willing to accept or make whatever works, right?… And I think that’s what Seneca was saying.” — Ryan Holiday (06:39)
• “We’re like actors in a play. We’re not the author, we’re not the playwright, but we have to really embrace the role that we’re assigned…” — Ryan Holiday referencing Epictetus (07:24)
• "Be humble. Be flexible today. Make the most of it." — Ryan Holiday (09:51)

3. Resilience Without Pretense

• (07:18-09:58)

• True Stoicism is not about pretending every hardship is a hidden blessing, but about refusing to be shattered by setbacks.
• Approaching life with humility (“settle for the old pair of trousers”) and willingness—to start small, to make contributions where possible—creates resilience and opportunity for genuine impact.
• Seneca’s greatest philosophical works emerged as his public and political options dwindled: making virtue from necessity.

Notable Quotes:

• “It's naive to think, oh, you can turn everything into a wonderful positive... It's ridiculous and offensive to be glib to say oh, just focus on the good. No, what we're saying is that there's some good that can be derived from this.” — Ryan Holiday (08:23)
• “We can settle for something as opposed to taking our ball and going home, crying about it, feeling persecuted about it, throwing up our hands, giving up because of it.” — Ryan Holiday (08:49)

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Memorable Moments & Timestamps

00:11 – The myth of Stoicism as a “written” philosophy is debunked

01:44 – Emphasis on Stoicism’s roots in conversation and community

05:03 – Reading from Seneca on adapting to circumstances

06:09 – Lincoln’s parable of the job-seeker and the old trousers

07:24 – The “actor in the play” metaphor from Epictetus

08:23 – Stoic realism: acknowledging hardship but seeking opportunity within it

09:51 – Episode’s closing exhortation: "Be humble. Be flexible today. Make the most of it."

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Conclusion

This episode of The Daily Stoic Podcast encourages listeners to remember that Stoicism lives not in silent solitude but in shared dialogue and in how we adapt to life's changing circumstances. By drawing lessons from both ancient Roman philosophers and American leaders, Ryan Holiday reminds us to be humble, flexible, and effective—engaging fully with the roles life hands us, no matter how unexpected.

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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. This is how it's meant to be done. Because so much of Stoicism comes down to us in books, it's easy to assume that it's a written philosophy, that philosophy was something the Stoics did alone, in private, hunched over a wax tablet or some unfurled scroll. Isn't that how we got Meditations or Seneca's letters? Yeah, but that's not how we got the philosophy itself. Stoicism began on a porch in Athens, the Stoa Pokele, the painted porch, where Zeno would talk and trade ideas with whoever was around. The great playwright David Mamet had a funny way of putting it. On the Daily Stoic Podcast a while back. He says what he loves about the Stoics is that they were just porch guys, just regular people hanging out, talking about how to become the best version of themselves. Cato, the man widely admired as one of the greatest Stoics. We don't even have secondhand reports of his words, but we know that he liked to do his philosophizing on foot. Or Plutarch tells us that he would take meandering walks through Rome, talking with whomever he met on his rounds, and that for all his austere habits, he loved philosophical dinner parties where they talked about ideas long into the night. You know, Epictetus never wrote anything down. His discourses comes to us from a student who tells us that whatever he used to hear him say, he wrote down word for word, as best he could, as a record, for later use of Epictetus thoughts and frank expressions. And that's how Epictetus taught in person, going back and forth in real time. So for most of its history, Stoicism was a spoken, conversational philosophy. It's meant to be heard, meant to be talked about, meant for that, back and forth. And it's a great tradition that we're a part of, one that's gone on unbroken for thousands of years. And by the way, we are continuing it here with Daily Stoke. And me, Ryan Holiday. I'm gonna be hitting the road the old way here very soon.

[B]

As part of the Daily Stoke Live

[A]

tour, I'm making the rounds. I'm going to be in Portland here in early June, San Francisco, then Chicago, Boston, dc, Detroit, Australia, Midwest, east coast, all over, even New Zealand. And I'd love to see you come, ask me questions, trade ideas, hang out,

[B]

talk to me, talk to other Stoics, grab Your tickets@daily stoiclive.com.

[A]

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[B]

it is well to be flexible. Begins with a quote from Seneca on tranquility of mind. He can't serve in the military. Let him seek public office. Must he live in the private sector? Let him be a spokesperson. Is he condemned to silence? Let him aid his fellow citizens by silent public witness. Is it dangerous to enter the forum? Let him display himself in private homes, at public events and gatherings, as a good associate, a faithful friend, and a moderate tablemate. Has he lost the duties of a citizen? Let him exercise those of a human being. And then the story, it's one of my all time favorites. I loved this the first time I heard it. Shortly before his death, as victory in the Civil War was finally within his grasp, Lincoln told a story to an audience of generals and admirals about a man who had approached him for a high ranking government appointment. First, the man asked if he might be made a foreign minister. Upon being turned down, the man asked for a more modest position. Upon being turned down again, he asked for a job as a low level customs officer. Finally, he could not even get that. He finally just asked Lincoln for an old pair of trousers. Ah. Lincoln laughed as he concluded the story. It is well to be humble. This story embodies the flexibility and the determination of stoicism. If we can't do this, then perhaps we can try that. And if we can't do that, then perhaps we can try some other thing. And if that thing is impossible, then there is always another. Even if that thing is just being a good human being, we always have some opportunity to practice our philosophy, to make some kind of contribution. You know, I love this story and I think the lesson that Lincoln was trying to say is that you find your role, you're willing to accept or make whatever works, right? And I think that's what Seneca was saying. And I suspect Seneca was also telling this story, you know, near the end of his life as the options in public life were closing to him. You know, okay, so Nero turned out to be insane. Okay, so you're forced into exile, you know, all throughout Seneca's life, in fact,

[A]

he's, he's forced to, to adjust, to

[B]

accommodate, to make the best of a bad situation. And for the Stoics, this was the resignation. Not like resignation like, oh, everything sucks. What am I going to do? But like, oh, this is the role I've been assigned. I'm going to act the hell out of it. And this is something that Epictetus talks about as well. You know, he says that, you know, we're like actors in a play. We're not the author, we're not the playwright, but we have to really embrace the role that we're assigned and this ability to be flexible, to not go, oh, but I only operate at this level. I'm a Harvard grad. I could not possibly accept X, Y or Z. This makes us really fragile because life is going to humble us. Life is going to put us in unfamiliar situations. But you, the person who can adjust, who can say, yeah, I'll start here. I might work my way back up. I might be such a stunning actor in this role that I get promoted or I get noticed, but I'm not gonna put on any airs. I'm not gonna close myself off to anything. I'm going to embrace this, right? And this is something I think about, obviously, when I talk about this idea of the obstacle is the way it's naive to think, oh, you can turn everything into a wonderful positive. That's not what it is. It's not, oh, this horrible thing happened. But by some magical trick, I turn it into the best thing that ever happened to me. The loss of my father, or the loss of all your money or the loss of your job or the loss of this or that. It's ridiculous and offensive to be glib to say, oh, just focus on the good. No, what we're saying is that there's some good that can be derived from this. There's something positive. We can. We can move the ball forward in some way because of this. It's not to say we would have chose it to be happy. We can settle for the old pair of trousers. That's Lincoln's joke, right? We can settle for something as opposed to taking our ball and going home crying about it, feeling persecuted about it, throwing up our hands, giving up because of it. And that's what Seneca ultimately does as well. You know, his great writing towards the end of his life comes as these other doors have been shut in his face. And I would argue he makes his largest contribution through this writing. And that's why we're here talking about it today. So be humble. Be flexible today. Make the most of it. Talk to you soon.

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