The Daily Stoic - Decide What to Be and Go Be It | How Would The Stoics Handle Social Media Envy?

Episode Date: July 14, 2026

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Welcome to the Daily Stoic podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world. Decide what to be and go be it. In a way, it's easier to think about the greats as being made of superior stock. To think of Cato is coming from a long line of distinguished ancestors. To think of Marcus Aurelius as being someone who's naturally wise and decent. it lets us off the hook to think of virtue as something someone is born with, as something all or nothing. But as we've talked about many times, Aristotle's insight was that this is nonsense. Virtue is no different than any other skill.

You don't have it. You do it. And you get better at it, the more you do it. If you want to be generous, if you want to be brave, if you want to be honest, if you want to be tough, if you want to be an early riser, it's not a complicated formula. In fact, by wanting to be those things, you've already taken an important step. First, say to yourself what you would be, Epictetus tells us, and then do what you have to do. The second part is harder, but hardly complicated. You start tipping bigger.

You start doing the stuff that scares you. Stop dancing around your real opinions. You push yourself physically. You set your alarm. And in doing this, you become what you wish you were. And that's basically what we built the daily stoic habits for success, habits for happiness challenge around. It's six weeks of forcing you to be the habits, to do the virtue that you know you're going to want to have and to be. It's daily actions that compound into long-term habits

and results. There was a study by the University College of London that shows it takes something like 66 days to establish a habit for a behavior to become automatic, to become part of who we are. And so I want you to think about who you could be two months from now or who you could be right now had you started two months ago. That wasn't that long ago. That was May, right? How quickly that time has passed. But how long habits that you had started then could last, could endure, could be a part of you had you picked them up. I don't want you to let any more time pass by. When you just think about what a habit would be worth if you started it today, if you had it established by September. And that's what the course is. We built this course many years ago.

It's helped thousands of people all over the world build habits step by step and develop lasting change in their lives. But we updated it now for this moment. We wanted to keep the things that worked. We wanted to add some new ones. We added some great new tools to help you reflect and and sort of meditate on the changes you're making. There's also a great new community space because I think habits are something best done with others. It's really awesome. We're going to start it on July 21st,

so I'd love to see it in there. We're offering a group discount if you enroll with some of your friends. And you can sign up today at dailystolic.com slash habits. We're traveling internationally this summer, and some of those places like in Europe, you know, you can't just go dress like your sloth. Bobby American. You got to dress up a little bit. Can't show their shoulders. Can't wear shorts.

So I'm going to take some of the stuff I bought from Quince because it holds up well, looks good, it's fancy without being uncomfortable. I'm going to try to pack clothes that are light, airy and comfortable. I can use them in multiple settings. You've certainly seen me in some of these things if you've ever watched the Daily Sto of video or seen me talk live. I want something that looks good on stage that I'm not going to sweat through. That's not going to get super wrinkled. Quince has got great t-shirts. They've got great light sweaters. And everything at Quince is priced 50 to 80 percent less than similar brands. They work directly with ethical factories and cut out the middlemen so you're paying for quality, not brand markup. And Quince goes way

beyond clothing. They've got sofas and ceramic cookware, premium betting. It's the kind of brand you end up recommending to everyone for everything. Elevate your summer wardrobe. Go to quince.com slash stoic for free shipping on your order and 365 day returns, now available in Canada too. That's Q-U-I-N-C-E dot com slash stoic for free shipping and 365-day returns, quince.com slash stoic. Most leaders have a clear picture of how work is supposed to get done,

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Welcome to another episode of the Daily Stoic podcast. When I was in Portland, I went to one of my favorite bookstores, which was Powell's. I've done a talk there before, but it's been a while since I went, and my wife had never been. So we went up there. She was looking for stuff. My son picked out these books, these graphic novels,

and it was just so lovely to see him reading in the car, just something he's not done before or had any real interest in doing and just be like, oh, I forgot my book in the car. Can you bring it in? I want to read it while we're eating. It's like, okay, buddy, of course. So that was lovely.

Two funny things at pals. Number one, I took them up to the rare book room. They like things that are like first editions are cool. I think they hear about it like with Pokemon cards or, you know, like they're usually. YouTubers are like, it's a limited edition drop of some, you know, dumb toy or whatever. So I was like, do you want to see some really cool stuff, limited edition things? I took them up there and I'm showing them all this different stuff.

And they're like, Dad, how much is this one? And I was like, well, it's expensive enough that they don't have it here. It's in a safe location. He's like, well, how much is it? And what is it? I was like, oh, it's like a first edition of Lewis and Clark's, you know, like, journey or whatever. And he's like, and how much is it?

And I was like, $250,000. And he's like, can we get it? And I was like, you clearly have no idea how much $250,000 is. But that book is as much as a house. And so, yeah, we're not going to get it. And then when I linked up back with their mom, they're like, Dad wouldn't buy us this book. So that was insane. But no, I went up to the desk and I said, hey, you know, I'll sign any copies of my books if you've got them.

Now, Powell's also has used books. And so they got all the copies in them. I'm signing the books. And some of them are already signed, like, because they've done, like, the public Pushers over the year sometimes does a limited run of for Zokes. But one of them had been bought from the painted porch. It had the painted porch stamp in it and it was signed. So that was hilarious.

I guess someone will buy that sign book twice, maybe. Anyways, Portland was awesome. And as I said, my kids were with me. They got to run the mics during the Q&A. So I'm going to bring you a couple of the questions from the Q&A. I brought you some, I think, earlier a couple weeks ago. But anyways, I'll bring you the Q&A. My kids were running up and down, handing them.

mic deciding who they wanted to pick. So that was really cool to see. And if you want to come, see me live and ask me some questions, I'm going to be on tour. As I said, I've been telling me about all the dates and going Australian, Auckland, in October, I think in August, like Chicago, Minneapolis, Detroit, then there's some East Coast dates, a bunch of places. I would love to see all of you. I'd love to answer your questions. Maybe my kids will be running mics again. You can grab tickets at Dailystoiclive.com. They just added the Nashville date in November as well. well. I didn't really know what I was going to ask until I had this situation last night as I was thinking about coming here. So this is kind of a creative field, a question that I wanted some insight on. How do you talk to someone whose ambition and drive are real and admirable, but whose definition of success has become incredibly externally focused that it's actually becoming an obstacle in itself. and someone who reads any skepticism of their plan as a lack of belief in them personally.

Yeah, I've come to say that I am very ambitious as a writer and not as an author. And by that, I mean, I'm very ambitious and focused and driven in the part of what I do that I can control, and I'm more and more indifferent about the things that I don't control. So I want the book that I'm working on now to be the best thing that I've ever done, to really push the boundaries of what I'm capable of, to be a leap forward in all these ways. And I'm thinking very little about its commercial prospects. Now, as I've gone that direction, the irony is that I've experienced more and more success. Like I was much more focused on my first books and my first projects. How were they received?

How many copies did they sell? What awards did I win? Where did I land on the bestseller list? And what I realized ultimately was not only was I making myself unhappy because sometimes it happened, sometimes it didn't, and I was crushed when it did happen and I felt awesome when it, when it did. But that I was putting my happiness or my definition of success on something that wasn't up to me. I was also expending a lot of time and energy, emoting about thinking about dreading, praying for, you know, pining for the parts that were not up to me. Does that make sense? So you have to ask yourself, is your goal, is the thing you're ambitious about, is what you're

driven about, is this something that you get to decide or not? Or are you saying, hey, I'm working really hard so these people over here will pick me or these people over here will recognize me or this supposedly meritocratic system, but probably not meritocratic system, will select me or anoint me or whatever. That's a bad use of your ambition and drive because it's not in your control. You want to focus your energy and effort. to the parts of it that are up to you, which is usually doing the thing, working hard on the thing. And that's kind of how I think about that. First of all, thank you so much.

Your takes on stoicism and everything has truly, like, actually changed my life. So thank you so much for that. I appreciate that. My question kind of revolves. You talk a lot about, like, the path of Hercules and Masonius Rufus and kind of, like, doing the hard thing and having that endure. When we're trying to choose the hard, right path and we keep kind of relapsing. and going back, thinking about things that we're trying to overcome.

Do you have maybe tangible examples from your life or perhaps from Stoics throughout history of how they were overcoming those mental challenges in their life? Yeah, so the choice of Hercules, it's a story that Zeno hears in the Athenian Agora that sets him on the path to philosophy. Hercules, as a young man, comes to this crossroads and has to choose between the easy way and the hard way, right?

Getting everything he wants and having to work for. it. It's the choice between virtue and vice. Ultimately, it's like, it's that resistance that we're talking about. Are you going to do the thing that challenges you that's hard that makes you better? Or are you going to, you know, do what everyone else is doing or, you know, take the easy way? I mean, I think it's a constant, it's a constant challenge. It's not a choice we make once in our life, but we make, you know, constantly throughout our lives. And this choice really, it says a lot about us. Epictetus would talk about how. how if you want to be beautiful, you got to make beautiful choices.

I just think about, like, hey, what does this choice say about me? You know, am I more often than not, am I on a consistent basis making the choices that are consistent with the person that I want to be or the place that I want to get? And I think that's kind of the test that we have to ask ourselves as we face, you know, little choice about what you're going to eat for dinner, what time you're going to wake up, and then also when you face kind of ethical quandaries or challenges, you know. Am I going to wish I did this differently later on down the road? Am I going to wish I did more than I'm doing right now?

And I think that dilemma should, you know, sort of hover over us. You said, and I love it, you're always free to have no opinion. Yeah. But I was wanting to push for justice. Yeah, so the Stoics are saying, look, do you have an opinion about everything that's happening in the world? You're going to have a lot of opinions about things that you have no say over. And this is like a recipe for misery. Like if I was to put a curse on someone, I might say, like have a bunch of really

strong opinions about everything that's happening everywhere in the world, right? And clearly someone put this, this hex on Elon Musk at some point. And it broke his brain. But sometimes people take this to me when I talk about like, hey, having fewer opinions that I'm talking about, you know, injustices or evils that are happening in the world or that you would be somehow politically disengaged or sort of, not know what's happening in the world. I don't think that's what it is at all. I'm actually saying that when you have fewer opinions about frivolous, insignificant things, it can free you up to have

a handful of opinions about, you know, some core issues that maybe you actually can be engaged and involved in. I also think, like when I think about this with my kids or my family or my life, like how often we have opinions about things that nobody asked for that in the big picture won't matter. And yet because we have those opinions, because we take those stands, what it does is it creates conflict and disagreement and tension and arguments. So it's like, you know, more wood behind fewer errors, as they say. There are significant things that the Stoics have had, you know, big opinions about. That's where you take your stand.

That's where you get involved. And then the rest of the stuff, you know, you can be, as they would say, more indifferent, too. Hi, Mr. Holliday. I just want to say thank you for your talk. That was really awesome. I just got into Stoicism. So I was wondering what, like, books you would recommend, including your books, too. Yeah. Okay. So if someone wants to get into Stoicism, where should they start? Right. This is the ultimate question. I think Mark Shrewis' Meditations is one of the most incredible books ever written. It's the private thoughts, the most powerful person in the world trying to be,

better, trying not to be dyed purple, as he said, which is corrupted by the absolute power that he has. But the problem with meditations is a little bit disjointed and a little bit random. Some people struggle with it because, you know, it's just random thoughts smattered throughout. So sometimes people struggle with meditation. So the next recommendation I give them is a collection of Seneca's essays called On the Shortness of Life. That's probably Seneca's most powerful essay on the Shortness of Life, which has all his thoughts on time and death and, and the urgency of life. It's got a couple other collections in there.

Seneca's letters are also quite good. I think, you know, the Penguin Classics edition of sort of his best letters is one I often recommend to people. Epictetus has sort of two works. The totality of his lectures that survived to us are known as the discourses, which is, you know,

him talking to his students about a variety of things. Kind of like, you know, talk like this. He's talking. Someone's writing down everything I said over many, many months, that would survive to us as discourses. Then there's basically a shortened collection of the discourses that survives to us and it's called the Incuridian, which just means like a handbook. That's like the Handbook of Epictetus.

You can also just get the Inc. The Inc.oridian is what Stockdale's philosophy teacher gives him before he leaves for what ultimately is Vietnam. And that's the book. He basically has memorized and gets him through seven years of torture and imprisonment and solitary confinement. So that's kind of the big three of the Stoics. There's a handful of other texts I recommend. There's a collection of Musonius Rufus' lectures that survived to us called That One Should Disdain

Hardship. It's kind of a janky, hard-to-follow title. But I also like Pierre Hadoes works on the Stoics. I like Donald Robertson's books on the Stoics. So that's kind of my sort of Stoicism reading list for you. If I got this right, the Stoics use Preeto Medi-Medatatio-Milorum. Is that how you? Yes.

A premeditation of evils. Yeah, so contemplating in worst case scenarios to dissolve their sting as a strategy for dealing with anxiety. And if I have it right, I think they avoid the opposite. So contemplating best case scenarios. Set me straight if that's right. And if it's not, what's the harm in contemplating best case scenarios? These days, people talk a lot about positive visualization, imagining it going right, walking yourself through it. I don't think the Stoics have any problem with positive visualization per se.

Their practice of what is effectively negative visualization was based on the premise that the unexpected blow lands heaviest. That's what Seneca says. He says that you should be aware of the things that could happen and be prepared for them, right? He quotes a Roman strategist who says that a leader is never allowed to say, oh, I didn't think that would happen. right your job is to think about what could happen and have a plan B and C and D and E you know just a couple days ago was the uh the anniversary of D day and Eisenhower would talk about

how plans are worthless but planning is everything and I think that's what premeditosham Malorum is it's it's understanding that hey the chances of this going exactly how I want it to go are pretty low right because so much of what happens in the world is not in our control so I don't want to be in a place where I am only good if things go the way that I want them to go. But if I understand they could go in these variety of directions and I have walked myself through what I would do if that happened. Or if I've just put myself in a state where I'm not expecting them to go any particular way, then I'm not going to be surprised. I'm not going to be thrown off. I'm not going to be disappointed or angry or feel singled out. I'm just going to be able to deal with

them. That's what the Stoic. practice is really about. So my question is, in the age of social media, I feel like a lot of, you know, social comparison, jealousy, you know, bad shit happens, basically. Yeah. And how do you think the soobics would react to that? And what's like a way that you can turn it into something positive in a way that you can, you know, get over it? Yeah. I mean, what social media does is take very human, timeless things and just exaggerate and make them more prevalent and stream. So we've always compared ourselves to other people. We just knew less about what they were doing. And the algorithm, you know, senses that these are strong, these illicit strong opinions. Like,

I've never picked up Instagram or Twitter or any of the social networks and then spent a bunch of time on them and then afterwards felt a lot better. That's not what makes the money, right? That's not what keeps you coming back. So understanding sort of what forces are operating on these algorithms, I think, is really important. I think the Stoics would be aghast at, you know, the idea of hate following someone or something or, you know, the idea of subjecting yourself over and over again to these sort of temptations to compare and contrast and compete. It says not great. Epictetus would talk about how, if you want to be happy, only run races where winning is up to you. That's what he said. And so, you know, if you're comparing yourself to other people, you don't decide if you win.

Right? Other things decide. But if you're comparing yourself to yourself, your own values and what you want, you know, you're in better shape. So, I mean, a lot of the choices I make as far as my social media habits and device things are about sort of winning those battles before they're fought by not having access to them, not checking them so often. You know, I try to sense what, what improves my quality of life. And if I don't absolutely have to do it for work or whatever, I just don't do it. And it's made my life a lot better. better. Cald-Newport has a great book I'd recommend called Digital Minimalism that has some great strategies in this regard.