The Daily Stoic - When Everything Feels Unpredictable, Hold Onto This

Episode Date: June 1, 2025

In moments of chaos, let Stoicism be your guide. In today’s episode, Ryan dives into how to tackle both small and big obstacles by harnessing your inner strength, staying steady in the face of unpredictability, and leading with purpose📕 Pick up a copy of the 10th Anniversary Edition of The Obstacle Is the Way by Ryan Holiday at dailystoic.com/obstacle🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us:  Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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For tickets, go to shawfest.com. Welcome to the weekend edition of the Daily Stoic Podcast. On Sundays, we take a deeper dive into these ancient topics with excerpts from the Stoic texts, audio books that we like here, recommend here at Daily Stoic, and other long form wisdom that you can chew on on this relaxing weekend. We hope this helps shape your understanding of this philosophy and most importantly, that you're able to apply it to your actual life.

Thank you for listening. Hey, it's Ryan. Welcome to another weekend episode of the Daily Stellar Podcast. Back in, I guess it was December, I did a talk. I talked about this. I went to the White House and I was talking to a group of people who are transitioning out of one administration, right? Everyone at the end of a presidential administration has to go find a new job.

It's just the nature of politics. And then a couple of weeks later, I did a virtual talk to this company called Ranstad, which is the world's largest staffing agency. They were trying to motivate and help their employees think about sort of going into the new year, but I was thinking a lot about this idea of this unfortunate reality that so many people

find themselves in right now, which is like, they're having to hustle to find a new job. They're having to hustle to avoid being laid off or companies that are having to face that reality. Obviously it's not as hard for them, but the idea of like, hey, the economic environment has shifted. There's this terror situation.

How are we gonna adjust? How are we gonna adapt? How do we keep the team together? How do we deal with the fact that the team can't be the same size that it once was, right? Maybe we over hired or, you know, as sometimes it's the exact opposite obstacle as it was for a lot of tech companies

in the middle of the pandemic, or suddenly they were massively under hired. It was this boom. The reality is when you are in business, when you're in politics, in life, you are going to be constantly experiencing less than ideal conditions. You are going to be suddenly thrust in unpredictable or difficult circumstances. And that's what today's episode is about, Me riffing on how we face these obstacles, how we deal with these difficulties.

You're in a world where suddenly a massive technological disruption like AI turns everything upside down. Or you had a position that AI is now threatening or challenging, or you suddenly have to figure out how to use, or you'll become obsolete. We're wrestling with this stuff here at Daily Stoic, too. or challenging or you suddenly have to figure out how to use or you'll become obsolete. We're wrestling with this stuff here at Daily Stoic too. How do you use these new tools? How do you stay relevant in a world where suddenly much easier and cheaper to do things that you

were laboriously and painstakingly making before? What does the world with tariffs look like? What can we afford? What are the margins on books and products? All of that is something I struggle with too. So when you hear me talk about this stuff, I hope it doesn't come off as glib because I certainly deal with it myself. And thanks to the wonderful folks at Randstad Enterprise for having me out.

Their CEO, Mike Smith was nice enough to invite me and mostly talking about the obstacles away, but I'm talking about stoicism in general I hope this message Lands well with you if you want to grab the obstacles way you can grab the 10th anniversary edition I will link to that in today's show notes. We've got signed copies of it in there. I hope you guys enjoy this talk Ryan thank you for being here. Welcome. I'm gonna hand over the floor to you and take it away. Yeah, thank you for being here. Welcome.

I'm gonna hand over the floor to you and take it away. Yeah, thank you so much. It's wonderful to be with all of you or I guess not actually be with you. Through the miracle of technology, I got to drop my kids off at school this morning and swim at Barton Springs. Thus the the goggle marks under my eyes, which I had hoped

would be gone by now. But no, it is wonderful. You might be asking, what does ancient philosophy have anything to do with modern life, let alone a modern business like yours? And I thought maybe I'd start with a story that does go way back, but I think illustrates what these sort of timeless ideas can add to life's obstacles, big and small.

So there's a Phoenician merchant named Zeno. He deals in what's called Tyrian purple, which was this rare purple dye painstakingly made in the ancient world that would create the color purple, which would later adorn the cloaks of the wealthiest Greeks and Romans, including the emperor. And Zeno is traveling with his convoy of ships in a time before venture capital and a time before insurance. And he suffers a shipwreck

and he loses everything in this shipwreck and he washes up in Athens penniless. And it's there walking through the Athenian Agora, the marketplace that he passes a bookseller. And this bookseller is reading aloud a famous story. This is the story known to us as the choice of Hercules. A young, talented man named Hercules is walking through the hills in Greece and it comes to a crossroads, basically the easy way and the hard way. And Hercules

famously chooses the hard way and by choosing the hard way goes on to be the sort of demigod that he was. And this story is supposed to symbolize the choice between virtue and vice, sort of self-actualization and self-abandonment. And it is in hearing this story, as he's down on his luck, that a prophecy that Zeno had heard as a young man suddenly makes sense to him. He had visited the priestess at the temple of Delphi and she had told him that the secret

to a good life was to have conversations with the dead. Oracles have always been rather vague. That's how their prophecies work is we bring to them the meaning that we want to see in them. And suddenly here, listening to this man read a story from Socrates, who was long since dead, that the prophecy suddenly makes sense to Zeno. He realizes that books are a way to have conversations with the dead. That's what reading is. I'm telling you now a story that's almost 24 centuries old. And when we pick up a book, we are conversing with, in most cases, someone who is no longer with us. That's why they call philosophy the great conversation.

So Zeno realizes that having conversations with the dead is the secret to wisdom, it's the path to the good life. And so he asks this bookseller where he might find a philosophy teacher and he's introduced to his philosophy teacher and he goes on to found the school of Stoicism on a porch not far from that bookseller. That's where the stoic and stoicism comes fromoic in Greek means porch. And so he becomes this famous philosopher who changes the course of history. And we're talking about now, 2,400 years later.

But Zena would joke later that he made a great fortune when he suffered a shipwreck. This thing that cost him everything, that blew up his business, that blew up what he thought the course of his life was supposed to be, was actually the best thing that could possibly happen to him, and sets in motion not just his great fortune, but our great fortune as well.

And I think the moral of this story is a few things. I also think it's just coincident. It's fitting, rather, it's fitting rather that that Stoicism would be a philosophy founded in a literal disaster, specifically a business disaster. I think that explains in part why it's so popular with CEOs and executives and leaders to this day. But to me the moral of this story, the essence of stoic philosophy, is basically this idea that we don't control what happens to us, we control how we respond

to what happens to us. So the fortune wasn't in the shipwreck per se, for Zeno, the shipwreck is in what he did with it. It was in his choice to carry on, right? To not give up, to not quit, to be open to new things, and then to follow that direction and make the most of it. So this is the idea of stoicism, that we control what we make of things. The stoic idea that the obstacle is the way is that we have in every situation, big and small,

desirable and seemingly undesirable disaster or a stroke of good luck, we have the ability to practice a virtue, we have the ability to practice excellence, we can learn, we can grow, and we can make this thing that we wouldn't have wished for, that we didn't ask for, that was our fault or wasn't our fault, that was historically unprecedented or totally commonplace. We have the ability to make it into exactly what we needed in that moment. We have the ability to

turn it into something that ultimately was good for us. There's a passage in Marcus Aurelius' meditations that I love. This is a guy who goes through disaster after disaster in his life, floods, wars, a devastating plague. He has health issues. He's having to run the largest empire in the world. And, you know, bemoaning a handful of these disasters in Book 5 of Meditations, he writes,

I was once a fortunate man, but at some point fortune abandoned me. But then he sort of corrects himself and he says, but actually true good fortune is what you make for yourself. He says, good fortune is what you make for yourself. He says good fortune is good character, good intentions, and good actions. And so the idea is that we get to use these situations we're in, again, the everyday and the utterly out of the ordinary. We get to use them to move forward in some way or another. I mean, certainly the pandemic was an opportunity to do this.

How many businesses and people that you guys have worked with, they had a five-year plan or a 10-year plan that had to become a five-week plan or they had to totally change the direction or the structure of their business or their operations. But the point is, look, we all had to figure these things out on the fly and we're still figuring them out on the fly because that's what life is about.

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For tickets go to sh Shawfest.com. And so what I wanted to talk today about is sort of the Stoic framework for how they do this. How do we turn the obstacle into the way? How do we take what seem like impediments or difficulties and return turn them into opportunities. And so for the stoics, the first part of this is in how we see things. What they would call the discipline of perception. There is, I think, a misperception of stoicism,

which is that it's emotionlessness. I would say that's not what stoicism is. It is though, trying to be less emotional. There's a great line from Epictetus, one of the stoic philosophers, he says, it's not things that upset us, it's our opinion about things. So stoicism is about trying to be clear-headed, to be objective, to see things as they are as opposed

to projecting onto them all of our worries, all of our opinions, all of our frustrations. It's to just take them as they are. Instead of focusing on who's to blame, why it happened, how unfair it is that it happened, how it's a disaster that it happened, they focus on, as I said, what are we gonna do about it? I think a stoic would be totally uninterested

in whether we're in a bull market or a bear market. They'd be like, that's not even a thing. These are just words we made up to describe a market, which simply is, right? If you're looking for a job or if you are a company looking to hire someone, whether it's a high employment or low employment, whether the market is good or bad is again irrelevant because you just have a specific problem in front of you and you have to figure out what you are going to do about that. And that's kind of what stoicism is.

It's understanding, again, emotions are important. You're not supposed to stuff them down and suppress them. But it is the idea that very rarely do we make good decisions in the sway of our emotions. I can be upset about something. I can be frustrated. I can be hurt. I can be angry about something.

But I have the ability not to hit send on the email that I have typed up in the sway of those emotions. That's what we're trying to do as the stoics. We're trying to say, hey, I want to zoom out for a minute. I want to think about how I'm going to think about this later. I'm going to, at the very least, not make this problem worse than it already is, right? That's what the discipline of perception is about. And there's two quick exercises from the Stokes here that I think are worth applying. One, I'm sure many of you guys are familiar

with the idea of a postmortem. A postmortem is the analysis you do after something has gone wrong or after something's been completed. You know, in the medical world, a postmortem is great for future patients. It's not so great for the patient

that died on the operating table. So the stoics have this exercise that we today call the premortem, which is the analysis in advance of what could go wrong so that we're not surprised when something like that happens. We have a contingency plan in place. Seneca said that one of the things a leader is never

allowed to say is, wow, I didn't think that would happen. Your job is to think about the things that could happen and to be prepared. Seneca talks about how he says, war, exile, torture, shipwreck, all the things of the human law should be before our eyes. And all these things happen to him. A shipwreck does happen to Zeno. And so the idea for the Stokes is that an unexpected blow

lands heaviest. But by anticipating and planning and stealing yourself in advance of something, you have the ability to at least not be rattled by it. And one of the places I think we would do something like a pre-mortem, this is where I tried to do it, is in another key stoic practice, which is the idea of journaling. I mentioned Mark Shulis' meditations earlier.

This is a unique historical text in that it is the private thoughts of the most powerful man in the world. He didn't have many people he could confide in. He didn't have a lot of people he could talk to. So it was in the pages of his book where he was doing philosophy for himself and in the truest form of self-help

that he worked through doubts, anxieties, worries, contingencies. And so I think there's something, especially in a very busy, noisy online world, there's something very valuable about spending some quiet time with some pages where we talk through what we're thinking about, what we're worried about, what we're concerned about, what could go wrong, what we're trying to improve.

And creating space to do this is one of the key stoic exercises. I would say it's almost impossible to separate the stoic practice from the journaling practice. However, stoicism is not just thinking about things, it's not just solving it in your head. Otherwise, if stoicism was just manifesting the reality you wanted, I probably wouldn't be telling you

to do a pre-meditatio malorum, because then we'd be bringing evil thoughts into the world. Stoicism is ultimately about the actions that you take. We don't control what happens. We control how we respond to what happens. We control what we do about the situation we're in, the obstacle we're in, the job market that we're in, the technological environment, the political environment.

We control what we do about it. We control how we respond. The problem the Stokes would say is that what we do about most problems is nothing. We hope that it'll resolve itself. We hope it will go away. We hope someone else will take care of it. Seneca says this is actually the one thing that all fools have in common. He says they're all getting ready to start, right? Instead of doing something about it, instead of taking some kind of concrete action, they're just waiting. They're waiting for the perfect moment, they're waiting for the perfect sign, they're waiting for permission and you have to do it. That isn't to say that we solve all of our

problems in some, you know, single bound or single swoop. One of my favorite passages in meditation is where Marx really is a guy who would have had considerable power at his disposal talks about how we assemble our life, we solve our problems, action by action, step by step. He says no one can stop you from that, right? The idea of what's the next right thing. And often that next right thing is a very small thing. It's not always glamorous. It's not always significant. It might not even be noticeable.

But it is taking a positive bit of action. I have a writing rule that I heard from someone that I love. And it's pretty simple. It's just write two crappy pages a day. If you write two crappy pages a day. If you if you write two crappy pages a day, eventually you get to a crappy manuscript, which you can edit into being not a crappy manuscript. But if you are not writing the pages because you are waiting for inspiration, or

you are expecting it to be perfect as you go, you will never get anywhere. And so it's about taking action and taking action now. I think there's something fundamentally entitled about procrastination because it assumes you'll have later. The Stoics have this another Latin practice here, the idea of memento moria, a meditation on our mortality, who says you'll have tomorrow? Who says you'll have next year or next quarter? Or I'll get serious about my health after I retire, after my kids go away to college or or what we've been saying now for several years, like when things go back to normal, right? They're not going back to normal, there is no such thing as normal. And so

as you put stuff off, what you are giving up is not just the present moment, but you're giving up the certainty that is right now, like you have life now you have an opportunity now, take advantage of it or don't in meditation, the Mark shows talks about how we could be good today, but instead we choose tomorrow. And I've come to see that as one of the most insidious lies that we tell ourselves, right? The, oh, I'll do it in the morning. No, you won't. You won't. If you're

going to do it, you should do it now. And so this idea of not putting things off, doing the right thing now, too, I do think this is important. Stokes weren't just these pragmatic problem solvers who got through, you know, the bureaucratic red tape of life. But it was this idea of trying to be the best that you were capable of being because that's important, but also trying to make a positive difference in the world being being community-minded, being of value and service,

making up a positive difference in other people's lives. The Stoics were involved in public service, they make great works of art. I think when Zeno was saying that he made a great fortune by suffering a shipwreck, I think he was in part referencing was saying that he made a great fortune by suffering a shipwreck, I think he was in part referencing the fact that he went from this sort of pure commerce lifestyle

to this more meaningful and significant thing to him, which was teaching this philosophy. So finding that thing that you think only you can do, that thing that makes the biggest difference. Also, what is so exciting to me about what you guys do is that you get to help people find and do what they were meant to do. I think when you look at a great coach,

like a great sports coach, it's not just how much have they won and how great is their organization. But to me, the great organizations, the great leaders have incredible coaching trees under them. Like, what have their coaches gone on to do? What have their athletes gone on to do on and off the court and on and off the field? And so to be in a position where you get to help other people succeed, you get to open doors for other people is such an incredible and wonderful thing.

In fact, that's what the nickname of Cratees, the philosophy teacher of Zeno, his nickname was Cratees the door opener, because that's what a great teacher does is they open doors. They open doors to worlds and paths and opportunities that we otherwise wouldn't have known about. And so I do think that's an important component, too. When we're talking about obstacles and we're talking about overcoming them

and how they can have opportunities inside of them, the opportunity is not always for us. Sometimes we're just learning a lesson that the primary beneficiary is somebody else, someone we're mentoring, someone we're working with, a colleague, our own children. It's not just that we can solve this problem for ourselves. Sometimes we can't, but we can in struggling

with that problem, learn and uncover things that are beneficial and helpful to other people, which I think is the final element that I want to talk about here. Stoicism talks a lot about the idea of acceptance. There is this sort of agency and perseverance and fortitude about solving and, you know, blowing through things. But there's also, they use this word ascent. And they don't mean like ascent up a mountain, but A-S-S-E-N-T, ascent, like to accept something. And at the core of stoicism is accepting

that some things are not in our control. And a lot of life is out of our control. Macroeconomics, politics, the environment, the weather, except all this stuff is out of our control. We have to cultivate a kind of a willpower and a sense of confidence and strength that allows us to weather the storms that life is gonna throw at us.

Like, I'm sure you guys have had different experts on these things before who are really good at claiming to predict the future, telling us what the next big thing is. I'm not one of those people. And I would argue though that the one, the only thing we know for certain about the future is that it is uncertain, that there will be difficulty and disaster and problems and disruption. And Astog prepares for this. This is what a premeditatio melorum is partly about. We have to never forget, Seneca says,

Fortune's habit of behaving exactly as she pleases, which is to say Murphy's law is real and that she has a sense of humor. It's not going to go the way we want it to go. And we have to accept that and we have to be ready for it. And we have to be prepared to endure that, to endure not just setbacks and problems and heartache and all the things that life has in store for us. But also change. Change is the one constant.

And the stones talk so much about change. Everything that we like about this current moment came here as a result of change. And so too will the things we like about the future come from change, as well as the things we don't like about the future. And so if we can prepare for this, if we can accept it, I always loved Queen Elizabeth II had a motto of the royal household. Now, you'd think that this would be something

as sort of stagian traditional as the queen, would just be about keeping everything exactly as it was. In some ways, that's the Queen's job. But her motto for many years, which she borrowed from an Italian novelist, was if things are going to stay the same, then things are going to have to change. And the idea of being flexible and adjustable,

of having your sort of core values, your core principles, your core operating mission, and then being incredibly flexible and adjustable and accommodating and accepting of all the insignificant things that if you insisted on keeping stay the same would prevent you from continuing to do that thing. So as we enter a world of AI, as we enter a world of climate change, as we enter a world of other sorts of technological disruption or political dysfunction, we have to be willing to

adjust and accommodate and use these things to our own advantage if we want to keep doing this thing that we think is important. The Stoics talk about how we never step in the same river twice, because the river is changing and we are changing. And this, I think, is a much more formless way of going through the world, rather than maybe what sometimes people think Stoicism is, which is this kind of rigidity, trying to keep everything exactly as it is. To me, that is a recipe not just for becoming irrelevant, but it's also a recipe for misery and profound unhappiness. And so the Stokes though would say that,

yeah, as difficult as the last couple of years have been, one of the things we can take from that is a kind of a confidence. We got through it. We should be aware of our capacity. In fact, we should pity people who haven't been through adversity and difficulty because they don't have a strength, a sense of their capacity. They don't know how they're going to adjust

and accommodate changes and disruptions. So you want to think about what you've been through. You want to think about what it's taught you. You want to think about what you've been through. You want to think about what it's taught you. You want to think about what you've taken from that. And then that's exactly what we want to apply to whatever the future holds. We know we can get through what the future holds because of what we've been through in the course of our lives.

We've been through a lot. And what we take from that is a greater sense of our capacities. What we should take from that is a greater sense of our capacities. What we should take from that is confidence that we have earned. Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and would really help the show. We appreciate it. I'll see you next episode. If you like The Daily Stoic and thanks for listening, you can listen early and ad free right now

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