Winning Isn’t As Fun As It Seems | Find Yourself a Cato

There’s an old joke: When the Gods wish to punish us, they give us everything we’ve ever wanted. Look at most people who win the lottery. Look at most famous people. Look at most world leaders. To borrow an expression from one particularly unhappy world leader, what do they look like? They look like they’re tired of winning. Because winning isn’t actually as fun as it seemed like it would be...and most of what we want to win turns out to not really be worth it. This was Marcus Aurelius’ point.--And in today's Daily Stoic excerpt reading, Ryan discusses the importance of having a great and noble person in our minds at all times to help guide our actions by examining this quote from Seneca's Moral Letters: "We can remove most sins if we have a witness standing by as we are about to go wrong. The soul should have someone it can respect by whose example it can make its inner sanctum more inviolable. Happy is the person who can improve others, not only when present, but even when in their thoughts."📔 You can check out How Adam Smith Can Change Your Life at the Painted Porch.✉️ 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.

• 0:03Ryan Holiday?

  Welcome to the Daily Stoic Podcast. On Friday, we do double duty, not just reading our daily meditation, but also reading a passage from The Daily Stoic, my book, 366 Meditations on Wisdom, Perseverance, and the Art of Living, which I wrote with my wonderful collaborator, translator, and literary agent, Stephen Hanselman. So today, we'll give you a quick meditation from the Stoics with some analysis from me, and then we'll send you out into the world to turn these words into works.

• 0:42Ryan Holiday?

  There's an old joke, "When the gods wish to punish us, they give us everything we've ever wanted." Look at most people who win the lottery. Look at most famous people. Look at most world leaders. To borrow an expression from one particularly unhappy world leader, "What do they look like? They look like they're tired of winning, because winning isn't actually as fun as it seemed like it would be, and most of what we want turns out to not really be worth it." This was Marcus Aurelius's point. "When we look at history and other people, it's hard not to see how trivial the things we want so passionately are." But what if you don't realize that yourself? Or rather, what if you don't realize

• 1:27Ryan Holiday?

  that the presidency or a billion dollars isn't that meaningful until after you've given up everything to get it? After you've traded your marriage or your principles or your youth to accomplish it? "Now you're free of illusions," says a character in Ralph Ellison's Invisible Man. How does it feel to be free of one's illusions? The protagonist can only answer, "Painful and empty, painful and empty." In this way, we are almost lucky not to get everything we want, not to be allowed our trivial, passionate yearnings, because we are allowed to continue in ignorance. We don't have to do the hard work on ourselves and really look in the mirror. But of course, this is what a philosopher does all the time.

• 2:12Ryan Holiday?

  Instead of hiding behind luck's protection or instead of continuing to lie to ourselves that more and more and more will make us happy, they actually probe it. They question their desires. They look into the future and ask, "What would happen if all my dreams come true?" Why would I suddenly be happy then? Why can't I be happy now instead?

• 2:42Ryan Holiday?

  Find yourself a Cato. Today's entry from the Daily Stoic, March 12th. "We can remove most sins if we have a witness standing by as we are about to go wrong. The soul should have someone it can respect by whose example it can make its inner sanctum more inviolable. Happy is the person who can improve others, not only when present, but even when in their thoughts." Seneca's Moral Letters, 11:9. Cato the Younger, a Roman politician best known for his self-discipline and his heroic defense of the Republic against Julius Caesar, appears constantly throughout the Stoic literature, which is interesting because he didn't write anything down.

• 3:27Ryan Holiday?

  He taught no classes. He gave no interviews. It was his bold and brave example that made him such a commonly cited and quoted philosopher. Seneca tells us that we should each have our own Cato, a great and noble person we can allow into our minds and use to guide our actions, even when they're not physically present. The economist Adam Smith had a similar concept, which he called the impartial spectator. It doesn't have to be an actual person, just someone who, like Seneca said, can stand by and witness our behavior. Someone who can quietly admonish us if we are considering doing something lazy, dishonest, or selfish.

• 4:07Ryan Holiday?

  And if we do it right and live our lives in such a way, perhaps we too can later serve as someone else's Cato or a spectator when someone else needs it. The line from Adam Smith is in the wonderful book by my friend Russ Roberts, which you should check out. It's called "Adam Smith Can Change Your Life," we carry it at the Painted Porch. It's a must-read. But it's like, you know, in the cartoons, there's the angel on the shoulder and the devil on the shoulder, and who are you going to listen to? Or if you remember those bracelets, what would Jesus do, right? The idea is to have that person in your mind, whether it's Cato, or Marcus Aurelius, or your grandfather, or Abraham Lincoln, or Harriet Tubman, or whoever it is for you.

• 4:52Ryan Holiday?

  Who is your hero? And what decisions would they make in those situations? Because when I interviewed Annie Duke for the Leadership Challenge, she was talking about like getting to the outside of a problem, right? When you're in it, when it's you, you can get tied up in what you want to do or what your impulses say or what's easiest. But you want to get to the outside of the problem. And this idea of the spectator or the Cato or the hero, it allows you to think about it from someone else's perspective. So not like, what would you allow yourself to get away with? But what would so and so expect of you in this situation? The other version you can think about this is like, what would you do if your kids were watching? If they understood?

• 5:35Ryan Holiday?

  John Wooden was fond of a poem and the line said, "A little fellow follows you." And this is a similar idea, right? What would you do if your kids were watching? What would you do if anyone was watching? But allowing those standards to hold you to a higher standards than you might otherwise let yourself get away with. But then I think this is really the important part. This last sentence about if we do it right, if we live our lives right, perhaps we could be that way. So remember, Stoicism is about putting your own spin on it. It's about being the ideas. I think getting to a place where you yourself have lived your life in such a way, produced work in such a way,

• 6:19Ryan Holiday?

  made brave or virtuous decisions in such a way that you yourself can serve as a model for other people, right? So maybe even using that as your own standard. Who do I want to be, right? Who am I aspiring to be? And what would that person do in this situation? Would they take the shortcut? They phone it in? Would they do the expedient thing? Would they do the short term thing? You know, what would they do? And pushing yourself to be that person, that's to me what Stoicism is about. And I think, again, the example of Cato is so inspiring because for literally hundreds

• 6:58Ryan Holiday?

  of years, Cato was that example. Cato was that for Thrasia and for Seneca. For countless Stoics on down, Cato was the inspiring example. When I had Tom Ricks on the podcast, who's another great book, I highly recommend, First Principles, which we also sell in the bookstore. Cato was Washington's Cato. Washington built his whole life around living up to the example of Cato. And he didn't always get there, but he pushed himself to get there. And so, again, try to find that towering example. That's the first part. And let them guide your behavior. Let them call you, hold you accountable to what you're capable of being.

• 7:41Ryan Holiday?

  And then strive to be that in such a way that you yourself, for your children, for your colleagues, for your neighbor, for whomever, you yourself can serve as a kind of example for them.