Podcast appearances and mentions of Ryan Holiday

You only get so much time with them. This is how you're going to spend it?

Constantly fretting and being anxious about your kids does not make them feel like you care about them and doing it now certainly doesn't compensate for any neglect in the past.

Your emotions, moods, choices and the examples you set are affecting your kids, always.

A family road trip will test your patience, your plans, and your ability to stay calm when everything starts going sideways. In today's episode, Ryan reflects on the unexpected problems, meaningful moments, and parenting lessons that came from driving the West Coast with his family. He also shares the rule he tries to follow so that, no matter what happens, everyone still wants to take the next trip.

Every family has an uphill they're climbing, even as we're climbing our own.

If we want people to change, we have to give them a way to see the truth for themselves.

Our job as parents is to give our kids access to ideas and worlds, to surround them with books, to encourage them to go where their interests take them—even if we sometimes disagree, even if some of them make us uncomfortable.

A master does not actually master anything. The Stoics understood this.

One of history's most powerful rulers was shaped by a teacher he never met. In this episode, Ryan talks with Professor William O. Stephens about how Marcus Aurelius discovered Epictetus, why the former slave's teachings hit him so deeply, and how those ideas about freedom, power, and self-mastery helped shape the philosopher king.William O. Stephens is a philosopher specializing in Stoicism, ethics, and ancient philosophy. He earned his Ph.D. from the University of Pennsylvania and spent over 30 years teaching at Creighton University, where he is now Professor Emeritus. His work spans topics like friendship, ecology, and human nature, with a focus on Stoic thought. His latest book is Marcus Aurelius: Philosopher-King (2025), and he is also the author of Marcus Aurelius: A Guide for the Perplexed, Epictetus's Encheiridion: A New Translation and Guide to Stoic Ethics, and Stoic Ethics: Epictetus and Happiness as Freedom. Check out more of William Stephens' work at https://WilliamOStephens.com/

Don't wait. Don't hold back. Tell them. Tell them again.

Change is hard but it doesn't mean you have to be hard on yourself.

Make the memory. Play the game. Because this is what it's about.

The Stoics understood that the wealthiest person can still be a pauper—poor in peace, poor in contentment, poor in perspective.

If the point is for our family to be together, if the point is for us to have fun together, to relax together, to get closer together, we need to start much earlier.

You don't need to be an egotistical asshole to be successful. History is filled with powerful people whose pride ultimately destroyed them, from Caligula and Nero to Xerxes and Mussolini. The Stoics believed the antidote to ego was humility, self-awareness, reflection, and honest introspection. In this episode, Ryan explores the dangers of ego and the timeless practices that can help you keep it in check, stay grounded, and remain a good person as you become more successful.

In this episode of the Builder's Bookshelf, we break down Ryan Holiday's The Obstacle Is the Way and translate Stoic resilience into the real world of construction, where delays, conflicts, and pressure are part of the job. You'll learn how to shift your perception, take disciplined action, and become the kind of leader who turns obstacles into the very path forward.Enjoy Today's Episode and #BeNEXT

What destroyed the Roman Republic was not one man or one moment, but a slow collapse of trust, duty, and shared values. In this episode, Ryan and ancient historian Barry Strauss discuss the broken civic bargain, economic strain, political violence, and personal ambition that pushed Rome toward civil war. They also talk about Cato's refusal to compromise, Caesar's decision to cross the Rubicon, and the warning the fall of the Roman Republic still holds for us today.Barry Strauss is a bestselling author, classicist, military and naval historian, and one of the leading authorities on leadership lessons from the ancient world. He is a senior fellow at the Hoover Institution, the Bryce and Edith M. Bowmar Professor in Humanistic Studies Emeritus at Cornell University, and a leading expert on ancient military history. Barry is the author of ten books on ancient history, translated into twenty languages, including The War That Made the Roman Empire, Ten Caesars, The Death of Caesar, and his latest book, Jews vs. Rome: Two Centuries of Rebellion Against the World's Mightiest Empire.Follow Barry on Instagram | @barrystrauss

Your kids don't need you to pretend you have it all figured out. In this episode, Ryan talks with Jon Gustin, creator of The Tired Dad, about losing your temper, apologizing, repairing after mistakes, and why showing your kids that you're human can make them feel safer, not less secure. Jon Gustin is the founder of The Tired Dad LLC and the voice behind The Tired Dad, a movement built around showing up for what matters most. His book, The Tired Dad.: 100 Reflections on Showing Up for What Matters Most, is out now!Follow Jon Gustin on Instagram, YouTube, and TikTok.Listen to The Tired Dad & Tired Mom Podcast | Apple Podcasts, Spotify, YouTube

Discipline, as a virtue, is related to the other virtues. By controlling our urges or wants or lifestyle, we're actually in a better position to be courageous or just.

What matters isn't how you see yourself or how others see you. What matters is that you be what, and who, they need you to be.

Discipline, in this way, isn't just about action; it's about control. Control over our impulses, our desires, and even our most deeply ingrained habits.

You can always find a way if you try. And it's going to be an important moment.

Marcus Aurelius was checked by philosophy, but if he hadn't been, he could have easily been a Nero or a Caligula. The American Founders knew this well.

With Christopher Nolan's The Odyssey hitting theaters this week, now is the perfect time to hear the Stoic lessons hidden within this ancient story. In this episode, Ryan travels through Greece and Ithaca to share 12 lessons about ego, perseverance, discipline, temptation, and what it really means to make it home.

It's not our job as parents to give them everything they want. It is our job to help them with these very reasonable feelings. Listen to the full podcast episode with Dr. Becky Kennedy

“First, say to yourself what you would be,” Epictetus says, “and then do what you have to do.”

After recording their episode at The Daily Stoic Podcast studio, Ryan and Dr. Becky headed next door to The Painted Porch, where Ryan shared a few must-read book recommendations.Listen to the full podcast episode with Dr. Becky Kennedy

 How many of us wish we could tear ourselves away from our phones and spend more intentional time with our kids and families?

Ryan Holiday is a bestselling author and one of the most influential modern voices on Stoicism. His 12 books, including The Obstacle Is the Way, Ego Is the Enemy, and Stillness Is the Key, have sold more than 10 million copies worldwide. He's also the founder of Daily Stoic, a media company that reaches millions through books, podcasts, newsletters, and YouTube. In 2025, Ryan completed his four-book Stoic Virtues series and followed it with a sold-out international speaking tour. Shawn Ryan Show Sponsors: Sheath. The underwear of legends. Go to ⁠https://www.sheath.com/SRS⁠ and use code SRS for 20% off. Visit ⁠https://drinkag1.com/SRS⁠ to get a free AG1 Travel Case with 7 free AG1 Travel Packs in your Welcome Kit with your first AG1 subscription order while supplies last. Control Body Odor ANYWHERE with @shop.mando and get 20% off with promo code SRS at ⁠https://shopmando.com⁠! #mandopod For problems worth solving — get started with Claude at — ⁠https://Claude.ai/srs⁠ Ready to upgrade your eyewear? Check them out at ⁠https://roka.com⁠ and use code SRS for 20% off sitewide. Ryan Holiday Links: Website - ⁠https://ryanholiday.net⁠ Daily Stoic - ⁠https://dailystoic.com⁠ Ryan Holiday IG - ⁠https://www.instagram.com/ryanholiday⁠ Daily Stoic IG - ⁠https://www.instagram.com/dailystoic⁠ Painted Porch Bookshop IG - ⁠https://www.instagram.com/paintedporchbookshop⁠ X - ⁠https://x.com/dailystoic⁠ Learn more about your ad choices. Visit podcastchoices.com/adchoices

The ability to be content, to be grateful, to be happy? These are the real luxuries, if you think about it.

Children are a ticking clock. They are on their way to not being children.

The most powerful man in the world still needed rules to live by. In this episode, Ryan looks at the rules Marcus Aurelius seemed to return to again and again, especially when life was difficult, people were disappointing, and the responsibilities kept piling up.

Men may be looking for answers in all the wrong books. In this episode, Ryan is joined by bestselling author Steven Pressfield to talk about how great fiction can teach us about courage, honor, sacrifice, and the human experience in ways that facts and advice often cannot. Steven Pressfield is an American author of historical fiction, non-fiction, and screenplays. Steven wrote for 27 years before he got his first novel published. During that time he worked 21 different jobs in eleven states. Steven taught school, drove tractor-trailers, worked in advertising and as a screenwriter in Hollywood. He worked on offshore oil rigs, and picked fruit as a migrant worker. You can follow him on Instagram: @steven_pressfield and check out more of his work on his website: https://stevenpressfield.com/

Family fun hits different when there's a flight to catch. In this episode, Ryan and Sam talk about what happened when a spontaneous stop at a state park turned into tired kids, dragging feet, a looming flight, and Ryan suddenly rushing everyone through the family detour he had been excited for.

We should let our light shine…and also let sunshine keep us honest.

It can seem like they don't like what you like. It can even seem like they don't like you. That's what children do, after all, they try to discover what they like.

We haven't been who we want to be. The routine slipped, the momentum disappeared, and before long, we weren't just off track, we'd given up. How do we fix it?

We say our kids are important—but words don't matter. Our choices are what matter.

You can be successful and still not be flourishing. In this episode, Ryan talks with leadership expert Dan Coyle about the difference between living like a machine and living like a human being. They talk about why high performance can become hollow, where real meaning comes from, and why simple mantras matter more than we think. They also discuss the importance of community, the role of “yellow door” moments, and how the words you use shape the way you show up.Daniel Coyle is the award-winning author of the New York Times bestsellers The Culture Code, The Talent Code, and his NEW book Flourish: The Art of Building Meaning, Joy, and Fulfillment. Check out more of Dan's work on his website https://danielcoyle.com/

Maybe you don't get the job. Maybe that person says “no” to a date. Maybe you find out you don't actually enjoy playing the piano. So what?

They need literature. They need to know the myths. They need to know the riveting moments of human history.

As Epictetus said, “First tell yourself what kind of person you want to be, then do what you have to do.”

How often are you saying “no” when they want to connect, when they want to do something, when they ask for attention or time together?

There are all the things that wealthy people buy with their money. They buy nice cars and enormous homes. They pay for access. They hire help. But there is one thing that they cannot buy.

Our job is to drag them around, to expose them to things, to get them to where they need to be…but aren't they also doing the same thing for us?

The world feels broken, and it's easy to believe nothing is ever going to change. In this audiobook excerpt from Soul Boom, Rainn Wilson makes the case for a spiritual revolution and pushes us to wonder what would happen if we rejected cynicism and stopped building so much of our world around competition, greed, and ego.Rainn Wilson is an actor, comedian, author, podcaster, writer, and director. He is most known for his role as Dwight Schrute on The Office, for which he earned three consecutive Emmy Award nominations for Outstanding Supporting Actor in a Comedy Series. You can follow Rainn on Instagram @rainnwilson and Twitter @rainnwilson, and on soulboom.com. Listen to Rainn's Podcast on Apple Podcasts, Spotify, or Watch on YouTubeIf you like this chapter

For the Fourth of July, we're revisiting Ryan's conversation with Pulitzer Prize-winning historian Thomas Ricks about America's founding, the ancient ideas that shaped it, and the first principles the founders were trying to build into the country.In this episode, Ryan and Thomas talk about First Principles: What America's Founders Learned From the Greeks and Romans and How That Shaped Our Country, and why figures like Washington, Adams, Jefferson, and Madison looked to the ancient world for models of courage, discipline, justice, and wisdom.

July 3, 2026 - 8am: Trump continues defending his wealth after $2-billion-dollar disclosure Recap of Former Special Counsel Jack Smith sitting down exclusively with MS NOW's Nicolle Wallace for a wide-ranging interview National Park money funding Trump's DC renovations Ryan Holiday gives us his summer reading list Presidential Historian Doris Kearns Godwin joins live from North Dakota to discuss the opening of the new Theodore Roosevelt Presidential Library and the legacy of Teddy Roosevelt.  Maryland Gov. Wes Moore discusses his planned speech tomorrow to serve as counterprogramming to President Trump with a message that Democrats cannot cede 'Patriotism' to Trump To listen to this show and other MS podcasts without ads, sign up for MS NOW Premium on Apple Podcasts. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Life is going to ask you to wait sometimes. There will be people ahead of you. There will be things you need to learn. To be able to do this will take all of the Stoic virtues.

 If we don't believe we're capable of change, then we are definitely not capable of change.