BONUS | 8 Life Lessons Ryan Holiday Learned The Hard Way

Life lessons aren’t handed to us, they’re earned the hard way. In this bonus episode, Ryan shares the eight truths he had to learn through failure, patience, and time Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content coming soon: dailystoic.com/premium http://dailystoic.com/premium 🎥 You can watch this episode on Ryan Holiday’s YouTube Channel https://www.youtube.com/watch?v=T7yEl4mpQt8: https://www.youtube.com/watch?v=T7yEl4mpQt8 📚 Sign up for Ryan’s free monthly reading list newsletter: https://ryanholiday.net/the-reading-list/ 📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work":https://store.dailystoic.com/pages/wisdom-takes-work 🎙️ Follow The Daily Stoic Podcast on Instagram https://www.instagram.com/dailystoicpodcast/?hl=en: https://www.instagram.com/dailystoicpodcast 🎥 Watch top moments from The Daily Stoic Podcast https://www.youtube.com/@dailystoicpodcast on YouTube https://www.youtube.com/@dailystoicpodcast: 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 https://www.instagram.com/dailystoic/,Twitter https://twitter.com/dailystoic,YouTube https://www.youtube.com/@DailyStoic,TikTok https://www.tiktok.com/@daily_stoic?lang=en, andFacebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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.

• 0:55Ryan Holiday?

  Some lessons I have learned the hard way. Number one, you gotta chill out. When I think about the things that in my twenties I was so intense about, I cared so intensely about, I'm like, "What?" Right? I could have been more patient, I could have been calmer, I could have realized that the thing you're thinking about is never as important as you think it is. Another one is, don't say "maybe" when what you really want to do is say "no." Right? Don't say, "I'll think about it." Don't say, "I'll try." If you can't do it, if you don't want to do it, just say "no." As they say, "no" is a complete sentence. You don't owe anyone anything, and you certainly don't owe them an explanation. Number three, I should just always listen to my wife. Every big business mistake I have made, my wife told me beforehand, "That's a really bad idea."

• 1:40Ryan Holiday?

  You gotta learn whose judgment to trust. You've gotta learn who knows you better than you know yourself, and you've gotta be able to trust and defer. You can't fix internal issues with external accomplishments. Hitting number one in The New York Times list is selling millions of books, making money, doing all the things I've done. You know what it feels like? It doesn't really feel like anything. You think it's gonna be this big cathartic relief? It's gonna change things? It's gonna undo things? It never does. You can't fix internals with externals. If you think professionals are expensive, try hiring an amateur. Right? I've tried to get around hiring, I've tried to do stuff myself. It always ends up... Costing you. But I would say there's a caveat to this. Sometimes just because someone or something is expensive,

• 2:24Ryan Holiday?

  just because they're an expert, doesn't mean they actually know what they're talking about. And you can rack up very large bills and not actually move the ball forward in any way. Anger always makes stuff worse. I don't think I've ever lost my temper and then afterward thought, I'm so glad I did that. I'm so proud of myself. It's not how it goes. You always regret getting upset. Just like I was saying, you look back at the things you used to care so much about and you're like, why was that such a big deal? Character is fate, as they would say. I don't know why I expect it to be different than it was the time before. I don't know why I'm surprised when people have already told me who they are. You've got to look at the core of who they are, what makes them tick, because that's what you're going to get from them.

• 3:09Ryan Holiday?

  The last one is that it always takes longer than you expect, even when you take that into account. My first book came out in 2012. I don't think I hit the New York Times bestseller list until 2016 or 2017. I'd started my first website in 2005 or 2006. If you had told me at the time that that's how long it would take, I don't think I would have believed you and I don't think I could have handled it. It always takes longer than you think it's going to take. Take that into account, then double it and be ready for it to take even longer. I read a lot. It's sort of my job. You can't write without reading. But for almost 15 years now, once a month, I send out an email with my favorite book recommendations for that month. Books that I've been reading, books that I've been going through,

• 3:53Ryan Holiday?

  books that changed my life, that inspired me, that I think connect to what's happening in the world. And you can sign up right now at ryanholiday.net/readinglist.