You Should Ask Yourself This Question When You Mess Up | 9 Stoic Keys To Building Character That Lasts

Look, we all mess up. We take certain people or clients for granted and a relationship deteriorates. We get distracted and make an unnecessary mistake. We are overwhelmed by a passion or a temper and do something bad. We’re humans. It happens. What follows are consequences.---And in today's video excerpt from the Daily Stoic YouTube channel, Ryan defines nine key methods that the Stoics used to build character that will help steer you toward a new destiny.✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Ryan Holiday?

  Welcome to the Daily Stoic Podcast, where each day we read a passage of ancient wisdom designed to help you in your everyday life. On Tuesdays, we take a closer look at these Stoic ideas, how we can apply them in our actual lives. Thanks for listening, and I hope you enjoy.

• 0:29Ryan Holiday?

  You should ask yourself this question when you mess up. Look, we all mess up. We take certain people or clients for granted, and their relationship deteriorates. We get distracted and make an unnecessary mistake. We are overwhelmed by a passion or a temper, and we do something bad. We're humans, and it happens. What follows are consequences. The client leaves us. The mistake costs money to repair. An apology turns out to be insufficient. And what follows consequences is often regret and sometimes shame. Or for less self-aware anger and blame. We mope, we whine, we wish things were otherwise. We wish we weren't such a piece of shit. If only we had just, you know. And this sort of self-flagellation is not what Stoicism is about.

• 1:13Ryan Holiday?

  It's backward-looking, the worst, most pointless kind of personal evaluation. Indeed, when we mess up, when we come face-to-face with the consequences of our actions, we must ask, "What can I learn from this?" Literally, we can ask that to the client who is leaving us. "What can I do better next time? What warning signs did I miss?" We can look at our habits and study where we got distracted and made that boneheaded mistake. We can look at the payoff we got from that passionate indulgence and examine whether it was worth the costs. And in so doing, we can learn from the past without reliving it on a loop. One way to look at Marcus Aurelius's Meditations is that this is a book of calm, firm admonishments to himself after messing up. He was cruel to someone, and so the next morning, he wrote about controlling his anger. He'd been wasting time recently,

• 1:58Ryan Holiday?

  and so he wrote about the shortness of life. The examples are endless. He even hints at this at one of his best one-liners, when he says that we should look at every action and ask, "Why are they doing that?" And who does Marcus say that we should start this with? With ourselves. It is inevitable that you will do wrong. You may even mess something up five minutes after listening to this email. What matters, at least to the Stoics, is not the mistakes, particularly simple errors that are a fact of life. But it's what we do about them. What matters is what lessons emerge from the missteps and how we improve because of them, how we fix or make up for them. Because that's all we can do.

• 2:38Ryan Holiday?

  The most valuable asset a person can have, the Stoics would say, is character. In fact, there was an ancient expression, "character is fate." Character determined your destiny. If you had bad character, you might be successful in the short term. You might win honors, but eventually that would prove to be your undoing. Your hubris and your lack of ethics would eventually lead to your demise. If you had character, you'd be all right. That wasn't saying that life would be a piece of cake, that you'd get everything you wanted, but you'd be all right. So Stoicism was really about that, the cultivation of virtue, the cultivation of character. Right? Marcus really said that the whole point of life is to cultivate good character and do works for the common good. And that's what we're going to talk about in today's episode.

• 3:25Ryan Holiday?

  We say, "Oh, I'm ruined. I've been screwed over. This broke me. I'll never be the same." No. According to Marcus Aurelius, it can only ruin your life. It can only harm you if it ruins your character. So you have to know the bankruptcy, the divorce, the scandal, none of it actually matters in the big scheme of things. It only matters if you let it affect your character. Everything else is recoverable from. You can come back from everything but that. It only ruins your life if it ruins your character.

• 3:57Ryan Holiday?

  Three things I learned from the great George Raveling, Hall of Fame basketball coach, civil rights activist. The first one is always be reading. He told me that his grandmother told him that the slave masters used to keep money in books because they thought the slaves would never read them. The point being, there's money in books. There's freedom in books. There's a reason powerful people don't want you to... Number two, he has a great question. He says, "Are you going to be a positive difference maker today?" That's his question. "Are you going to be a positive difference maker today?" And that's a question I think about all the time, and I got that from him. The third one is, "You can learn from anyone." George Ravlin once said, "I was his mentor in an interview," which of course is preposterous, but I'll take the point,

• 4:39Ryan Holiday?

  which is that you can learn from anyone, including people who are younger than you. You can learn from anyone, even if they live very different lives than you, even if you disagree with them about 99% of stuff. You can learn from anyone. Anyone can be your mentor. And I learned that from George Ravlin.

• 4:57Ryan Holiday?

  Marcus Aurelius reminds us to meditate often on the interconnectedness of everything in the world. He talks about at night, when you see the stars, he says, "Imagine yourself running alongside them. Imagine yourself up there." Whenever I watch a sunset, whenever I people watch, whenever I look at some beautiful piece of scenery, I try to think about humanity as one giant whole. I try to think about all the generations that have ever lived, all the ones that will ever come. And I try to remind myself that we're all connected, we're all part of this, we're all one enormous organism, as the Stoics try to remind us, what's bad for that organism is bad for us. We're all connected, we're all part of this, we all share this. And I try to never forget that.

• 5:42Ryan Holiday?

  "Don't sweat the small stuff." It's great advice, but also, details matter. Zeno, one of the founders of Stoicism, said, "Well, being is realized by small steps, but it's no small thing." If you don't sweat the small stuff, the details that matter, that add up in a big way, you could lose everything. You could end up very far from where you want to be. So the key isn't that you don't sweat any small things, but you know what are the irrelevant small things, and what are the essential small things?

• 6:14Ryan Holiday?

  Musonius Rufus says, "If you accomplish something good with hard work, the labor passes quickly, but the good remains." He says, "If you do something shameful in the pursuit of pleasure, pleasure passes quickly, but the shame endures." Remember that. Working hard to do something good, and the good lasts forever. If you do something shameful for something short-term, for something pleasurable, to get one over on someone else, the pleasure passes quickly, but the shame, the stain, remains.

• 6:42Ryan Holiday?

  People suck. It's just a fact. And one of the fascinating things about Marcus Aurelius's Meditations is how often he returns to this very theme. He opens the book with a catalog of the kind of people you're gonna meet in the day. Frustrating people, jealous people, stupid people. It's just a fact. Even his famous passage about how the obstacle is the way, the impediment to action advances action. You know what he's talking about? He's talking about difficult people. He's not saying you write them off. He's not saying you cut them out. He's not saying you give up on humanity. He's saying that difficult people are an opportunity to be kind, to be patient, to be good, to get the most out of them. The obstacle is the way even is about this very idea. Difficult people exist and we have to put up with them and figure out a way to work with them. And we have to rise to the occasion of the people that we interact with.

• 7:31Ryan Holiday?

  There's this amazing story about Ulysses S. Grant. He's this promising young military officer. He serves honorably in the Mexican-American War. But then something goes wrong. He basically ends up working for his dad, selling firewood by the side of the road. And one of his old friends from West Point comes by one day and he says, "Good God, Grant, what are you doing?" And Ulysses S. Grant just looks at him and he says, "I'm solving the problem of poverty." Meaning that Grant doesn't care that he's doing this so-called menial job or that it's a humiliating occupation. All he cares about is that he's providing for his family. He's doing a good job. He knows that it doesn't say anything about him as a person. It's crazy to think that just a few years later, Grant would be the head of an enormous army. And a few years after that, he'd be the President of the United States.

• 8:16Ryan Holiday?

  To accept it without arrogance, to let it go with indifference. You don't let the lowly position change who you are and you don't let the high position change who you are either. None of it goes to your head. You know none of it says anything about you as a person and that's what really matters.

• 8:33Ryan Holiday?

  One of my favorite lines in Meditations, he says, "To accept it without arrogance, to let it go with indifference." Meaning that good things happen, we get awards, we succeed, we make money. Awesome, but that doesn't say anything about you as a person. We fail, we fall short, we get criticized. Great, that doesn't say anything about you as a person. Another translation, it says, "Receive without pride, let go without attachment." Sort of even keel, not being affected, not getting too high or too low, not identifying with any of it, but identifying solely with your character.

• 9:07Ryan Holiday?

  In meditations, Marcus Aurelius reminds himself not to be Caesarified, not to be stained purple by the cloak of the emperor. And this is ultimately the problem that Caesar faces, right? Caesar is corrupted by what happens to him. He's corrupted by power. Absolute power corrupts absolutely. Marcus Aurelius is the one exception to that rule, of course, but Caesar doesn't escape it. Ultimately, he's killed over it. But he's changed by his endless ambition, his drive, his need to be in control, his need to get his way. And this is why Cato resists him. This is why Cato fights against him. He knew that one person shouldn't have that power. The Roman Republic was not perfect, but Cato knew that it was better than the alternative. He knew that power had to be distributed. It had to be spread out.

• 9:51Ryan Holiday?

  There had to be checks and balances. And that's why Cato resisted Caesar so much.

• 9:59Ryan Holiday?

  When I wrote The Daily Stoic eight years ago, I had this crazy idea that I would just keep it going. The book was 366 meditations, but I'd write one more every single day, and I'd give it away for free as an email. I thought maybe a few people would sign up. Couldn't have even comprehended a future in which 3/4 of a million people would get this email every single day and would for almost a decade. If you want to get the email, if you want to be part of a community that is the largest group of Stoics ever assembled in human history, I'd love for you to join us. You can sign up and get the email totally for free. No spam. You can unsubscribe whenever you want at dailystoic.com/email.