The Daily Stoic - This Is How It's Meant To Be Done | It Is Well to Be Flexible

Episode Date: June 1, 2026

For most of its history, Stoicism was a spoken, conversational philosophy. It was meant to be heard, discussed, and worked through in the back and forth.🎙️ Listen to the episode with David Mamet on Apple Podcasts and Spotify📚 Pick up a copy of The Daily Stoic by Ryan Holiday🎟️ DAILY STOIC LIVE | Ryan Holiday is coming to a city near you! Grab tickets here | https://www.dailystoiclive.com/🎙️ AD-FREE | Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 VIDEO EPISODES| Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemailSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 Stoapokile, 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 Deo 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's 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 taught. 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 Stoic and me, Ryan Holiday. I'm going to be hitting the road the old way here very soon. It's part of the Daily Stoke Live tour. I'm making the rounds. I'm going to be in Portland here in early June, San Francisco, then Chicago, Boston, D.C., 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, talk to me, talk to other Stoics. Grab your tickets at daily Stoiclive.com. You know what silently kills sales teams? The inability to see what's happening in their pipeline. 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. 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. Pip Drive gives your team one complete, trusted record of every customer in deal. It's all centered around a visual pipeline where you can see everything, what stage a deal is in, what needs to happen next. And then you've got complete clarity on your entire sales process in a glance.

It's fast as setup, easy to learn, and genuinely delightful to use. Switch to a CRM built by salespeople for salespeople and join over 100,000 companies already using PipeDrive. And RLink gives you an exclusive 30 days free instead of the usual 14-day trial. No credit card or payment needed. Just head over to pipe drive.com slash stoic to get started. That's PipeDrive.com slash stoic. You can be up and running in minutes. 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 follow 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 his 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, he's forced to adjust, to 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 Epicetus 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 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 unfurre. familiar situations, but you, the person who can adjust, you 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 going to put on any airs. I'm not going to close myself off to anything. I'm going to embrace this, right? And this is something I think about, you know, obviously when I talk about this idea of the obstacle is the way. It's not, 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, you know, 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, some good that can be derived from this. There's something positive we can find. 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.