You Need To Take The Unfamiliar Road | Think About It From The Other Person's Perspective

What would you give for the key to unshackle you from the fear and laziness holding you back?💡 Challenge yourself to spring forward and become the person you aspire to be. The Spring Forward Challenge starts March 20, 2025. Visit dailystoic.com/spring and sign up now!👉 Get The Spring Forward Challenge & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life📓 Pick up a signed edition of The Daily Stoic Journal: 366 Days of Writing and Reflection on The Art of Living: https://store.dailystoic.com/🎙️ 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. 📢 Share | ⚙️ Manage Subscription

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

• 0:05Ryan Holiday?

  Welcome to the Daily Stoic Podcast, where each day we bring you a Stoic-inspired meditation, designed to help you find strength and insight and wisdom into everyday life. Each one of these episodes is based on the 2,000-year-old philosophy that has guided some of history's greatest men and women, help you learn from them, to follow in their example, and to start your day off with a little dose of courage and discipline and justice and wisdom. For more, visit dailystoic.com.

• 0:57Ryan Holiday?

  You need to take the unfamiliar road. We have our habits, we have our practices, we have the way we like to do things, the way we like to eat, the way we like to get to work. It's comfortable, it's also boring. It makes us lazy and fragile. General Sherman, the legendary civil war strategist, once explained that he lived by an old rule, "never to return by the road I had come." He didn't want to retrace his steps. He wanted to blaze new trails, cover new territory, challenge himself. And this philosophy isn't just military wisdom, it's a blueprint for personal transformation. The ancient Stoics understood this deeply. In Meditations, Marcus Aurelius writes about

• 1:42Ryan Holiday?

  "holding his chariot reins with his weaker hand," not just as an exercise, but as a metaphor for embracing discomfort and doing things in a new way. He realized that true strength comes from developing ourselves in all directions, not just where we're capable or secure. And this isn't always easy, but neither is life. Epictetus said that when a challenge is put in front of us, "to think of ourselves as an athlete getting paired with a tough competitor or aspiring partner." "You want to be Olympic class," he said, "this is going to take some sweat to accomplish." Yes, the unfamiliar path is harder. Yeah, it requires more effort.

• 2:25Ryan Holiday?

  But as any athlete will tell you, growth happens at the edge of discomfort and resistance. Iron sharpens iron. Each challenge makes you stronger. That's the whole aim behind the Daily Stoic Spring Forward Challenge, which we do every year. It's designed to bring you a sense of intention and clarity, help you simplify your life, challenge yourself and relationships, move you closer to what you're capable of being. And we want you to join us in the Spring Forward Challenge. I do it every year. Thousands of Stoics do it every year, all over the world. It's going to be 10 days of actionable Stoic-inspired challenges, video messages from me, a call where we get together and debrief on the progress. You can ask me some questions in there.

• 3:09Ryan Holiday?

  It's going to be awesome. And I don't want you to let another season pass by while you stay in your comfort zone. I want you to join me and thousands of other Stoics all over the world as we take an unfamiliar road, push our boundaries, challenge ourselves to do the harder, the different, the more untraditional way. And it's going to be awesome. It all begins with that first step, though, that commitment to not do it the way that you've always done it. I want to have you join us in there. Dailystoic.com/spring. And remember, if you sign up for Daily Stoic Life, you can get this challenge and all of our challenge as part of that membership is a value of 700-800 bucks. It's awesome. The unfamiliar road awaits. Will you take it? I hope so.

• 3:52Ryan Holiday?

  Join us either in Daily Stoic Life at DailyStoicLife.com or just join us in this challenge. Start small. DailyStoic.com/spring. I will see you in there.

• 4:10Ryan Holiday?

  This is from this week's entry in the Daily Stoic Journal, "366 Days of Writing and Reflection on the Art of Living," by yours truly and my wonderful collaborator, Stephen Hanselman, who I also worked on the Daily Stoic with. Today's entry, "Think About It From the Other Person's Perspective."

• 4:29Ryan Holiday?

  We tend to assume the best about our own intentions and the worst about other people's. Then we wonder why life is so full of conflict. The Stoics flipped this habit around, reminding themselves to be suspicious of their own first reaction and approach others first with sympathy. Powerful people are often surprisingly terrible at behaving this way. But Marcus Aurelius, the most powerful man on earth during his reign, was renowned for his humanity in dealing with others. He told himself always to take a moment to remember his own failings and to contemplate how another might see the situation. He reminded himself, as we should, that most people are trying their best, even though

• 5:14Ryan Holiday?

  that's easy to lose sight of in the rough and tumble of daily life. Let's remember that today and think about each interaction from more than just our own point of view. That's the Daily Stoic Journal Weekly Entry, and we've got some quotes from Marcus Aurelius here. He says, "Whenever someone has done wrong by you, immediately consider what notion of good or evil they had in doing it. For when you see that, you'll find compassion instead of astonishment or rage. For you yourself may have had the same notions of good and evil or similar ones, in which case you'll make an allowance for what they've done. But if you no longer hold the same notion, you'll be more readily gracious for their error."

• 5:59Ryan Holiday?

  Marcus Aurelius, Meditations 7:26. And then he says, "When your sparring partner scratches or headbutts you, you don't then make a show of it, or protest, or view him with suspicion, or as plotting against you. And yet you keep an eye on him, not as an enemy or with suspicion, but with a healthy avoidance. You should act this way with all things in life. We should give a pass to many things with our fellow trainees, for, as I've said, it's possible to avoid without suspicion or hate."

• 6:32Ryan Holiday?

  You know, I tell the story in Stillness is the Key. I opened part one, the perception part of the book, the story of Kennedy and the Cuban Missile Crisis. Kennedy and Khrushchev face off over some nuclear ballistic missiles placed on the island of Cuba. And what's so remarkable about this moment, why I look at Kennedy and why I think he embodies what Marcus Aurelius is talking about in both senses, both in the why did they do this? What are they trying to do? And also, you know, people are not great. They're going to try to cheat or pull one over on you, but you can't let that break you or make you bitter. You've got to be cognizant and aware of it. Kennedy thinks not just what he's going to do, but he's conscious enough to think, what is Khrushchev going to do?

• 7:17Ryan Holiday?

  What is Khrushchev trying to do with this? And in fact, Khrushchev's real fatal calculation is that he doesn't have a good read on Kennedy. He'd sort of bullied Kennedy at a conference, had seen Kennedy bungle the Bay of Pigs. He thought he knew Kennedy and he thought he knew America, but he didn't. He couldn't conceive of how America would react to these missiles right on that island. And Kennedy, though, realizes, especially when his military advisers are telling him, you got to bomb Cuba, you got to bomb the shit out of Cuba, we got to go in to avoid World War III. Kennedy knows that to do that, he thinks about Khrushchev, how they're in the same position. They're both leading these sort of loose coalitions and with divergent interests and

• 8:01Ryan Holiday?

  are human beings, but also heads of state. He's really able to think about Khrushchev's position. And he says, look, I'm not worried even about what Khrushchev's going to do in response to what I'm going to do. I'm worried about step six or seven in this chain of escalation. We think about things from people's perspective, not just because empathy is good, not just because justice is important, but strategically, it's essential. Right? When I was in public relations, you would see people get so consumed with the truth of what they had to say or their own experience or their own point of view, they couldn't conceive that the reporter has their own interests, that the public has their own interests and position to effectively- Navigate the world to be successful,

• 8:44Ryan Holiday?

  you've got to understand other people's perspective. You've got to think about what's going on with them. And this allows you to not only be more patient, more forgiving and more gracious, as Marcus says, but it also allows you to be more effective and successful at whatever it is that you are doing. So I urge you today to spend some time practicing, let's call it strategic empathy. It will make you better. But most importantly, as we saw in the Kennedy and Cuban Missile Crisis example, it may well save the world. It makes the world a better place if we are more empathetic with each other. As Seneca said, we're all wicked people in a wicked world. If we can understand this, we can be kind and patient and tolerant and understanding, we will all get more of what we want and need.

• 9:33Ryan Holiday?

  Hey, it's Ryan. Thank you for listening to the Daily Stoic Podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple of years we've been doing it. It's an honor. Please spread the word. Tell people about it. And this isn't to sell anything. I just wanted to say thank you.