The Daily Stoic

Sharon McMahon, aka "America's Government Teacher", hosted Ryan on an Instagram Live to discuss his recent experience at the U.S. Naval Academy. Invited to speak on the topic of wisdom, Ryan was informed just moments before his lecture that it had been canceled due to his decision to address the removal of books from the Academy's library. What was meant to be a conversation about wisdom quickly turned into a powerful lesson on censorship, free speech, and the challenge of living with virtue.Sharon and Ryan talk about the importance of confronting history honestly, the controversy around books labeled “too woke,” and the scary implications of silencing ideas in places meant to shape future leaders.After years as a high school government teacher, Sharon now runs the non-partisan, fact-based Instagram account @sharonsaysso and is the author of The Small and the Mighty.Check out Sharon's podcast Here's Where It Gets Interesting and follow her on Instagram @SharonSaysSo and on X @Sharon_Says_SoSharon's Substack: The Preamble.

For the Stoics, riches weren't evil but attachment to them was. In Part 2 of their conversation, self-made billionaire Robert Rosenkranz and Ryan dive into the power of living within your means, mastering your mindset, and finding deeper purpose in your work. They discuss how your upbringing influences your relationship with money, why detachment leads to true freedom, and what really defines success.Robert Rosenkranz became a self-made billionaire as a pioneer in private equity, multi-strategy hedge funds, and the insurance industry. He launched the acclaimed NPR program, Open to Debate, funded Impetus Grants to extend human healthspans, and is founding an innovative cultural institution in New York to showcase immersive work at the intersection of visual art, sound, music, and technology.

Happy Mother's Day this weekend to everyone!

It would be nice if we always had smooth sailing. But we don't.

Marcus Aurelius was the public face of an empire. Seneca published plays and books. Cato and Cicero ran for office. Epictetus was a slave to a powerful Roman, at his whim and his mercy. In other words, they knew what it was like to be criticized.

Wealth can free you—or consume you. Self-made billionaire Robert Rosenkranz joins Ryan to discuss how Stoicism can transform our approach to money, ambition, and identity. Robert shares how Stoicism has shaped his decision-making, honed his intuition, and influenced his mindset on wealth and living a fulfilling life. Robert Rosenkranz became a self-made billionaire as a pioneer in private equity, multi-strategy hedge funds, and the insurance industry. He launched the acclaimed NPR program, Open to Debate, funded Impetus Grants to extend human healthspans, and is founding an innovative cultural institution in New York to showcase immersive work at the intersection of visual art, sound, music, and technology.

Courage calls us and what do we do? We ignore it. We let it ring.

You could say something…you should say something. But…you don't.

If it's right, if it must be done….do it now.

The call for courage keeps returning, over and over. What matters most isn't what we chose before, but what we choose right now.Listen to the talk that Ryan was supposed to give at The Naval Academy: Apple Podcasts, Spotify, YouTube

If wealth meant fulfillment instead of finances, how rich would you be? In today's episode, Sahil Bloom, entrepreneur and author of The 5 Types of Wealth, joins Ryan to unpack how they balance ambition and fulfillment. They discuss the concept of having “enough”, their definitions of being wealthy, what we can learn from the Stoics about living a rich life, and more. Sahil Bloom is the owner of SRB Holdings, the managing partner of SRB Ventures, and author of The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life. He holds a master's in public policy and a bachelor's in economics and sociology from Stanford University, where he was also a four-year member of the Stanford baseball team.You can follow Sahil on Instagram and X @SahilBloom Sign up for Sahil's newsletter here: https://www.sahilbloom.com/newsletter

As dark as life can get, there are lovely things out there to cheer you up.

You will never be secure enough, powerful enough that you won't be afraid—that's the whole point of courage.

We are all fighting our own battles, we are all besieged by misfortune in our own ways.

You might know Ed Helms as Andy Bernard from The Office or Stu Price from The Hangover movies—but did you know he's also a serious history buff? He's especially fascinated by history's biggest screwups, better known as SNAFUs ("Situation Normal: All F**ked Up"). In today's episode, Ed joins Ryan to unpack some of these epic blunders, explain how history became an escape for him, and share why learning about the past can be surprisingly therapeutic.Ed Helms is an actor, comedian, podcast host, and author. Ed has starred as Andy Bernard in The Office, Stuart Price in The Hangover trilogy, We're the Millers, The Lorax, and much more. He hosts the podcast SNAFU and just released his book SNAFU: The Definitive Guide to History's Greatest Screwups. You can follow Ed on Instagram and X @EdHelms

By winning the morning, we reduce the power that the rest of the day—much of which lies beyond our control—holds over us.

We tell ourselves that this is all for the future, that someday, in some big moment of significance, we'll use it. But will we?You can grab the Right Thing, Right Now ebook for just $2.99 right now! If you prefer reading hardcover books like us, we have signed copies available over at the Daily Stoic Store, too!

We often ignore flaws in our body until they demand attention, but flaws in the soul are even harder to see—the deeper the damage, the less aware we are of it.Today's episode is an excerpt from The Tao Of Seneca produced by Tim Ferriss' Audio. Get the free PDF at tim.blog/senecaListen to other letters from Seneca:Seneca on Despising DeathSeneca on Conquering the ConquerorSeneca on Philosophy and FriendshipSeneca on Practicing What You PreachSeneca on The Reasons For Withdrawing From The World Seneca on Master and SlaveSeneca on Worldliness and Retirement

Just after 2 a.m. on April 11, the U.S. Senate confirmed retired Air Force Lieutenant General Dan Caine as the 22nd Chairman of the Joint Chiefs of Staff. As it turns out, Ryan had the opportunity to interview Gen. Caine a few years ago as part of The Daily Stoic Leadership Challenge.In honor of his recent confirmation, today's episode is Ryan and Gen. Caine's powerful conversation. Gen. Caine reflects on being one of the first pilots in the air on 9/11, the core traits every great leader must embody, and how to effectively inspire and guide a team toward a shared mission.General Dan Caine is the 22nd Chairman of the Joint Chiefs of Staff. He has flown more than 100 combat hours in F-16 aircraft. His total flight hours are 2,800. Throughout his career he was awarded the Defense Superior Service Medal, Distinguished Flying Cross, Bronze Star Medal with bronze oak leaf cluster and the Defense Meritorious Service Medal.

It was a dark world…and Marcus Aurelius desperately needed some light.

Check out the previous lectures from Ryan Holiday at the U.S. Naval Academy here:Courage: The Power Of Courage Discipline: The Life Changing Art Of Self-DisciplineJustice: Stoic Habits To Help You Live And Be Better

The right book at the right time is a powerful thing. In fact, it can change the whole course of your life.

We were born to work together like feet, hands, and eyes, like the two rows of teeth, upper and lower. To obstruct each other is unnatural.

"The body should be treated more rigorously, so that it may not be disobedient to the mind." — Seneca In today's episode, Ryan sits down with Bonnie Tsui - author, swimmer, surfer - to unpack the deep connection between our muscles and mental resilience. They dive into everything from the intelligence of muscle memory, what the ancient Stoics knew about strength that we've forgotten, how exercise can actually bulk up your brain, and much more. Bonnie Tsui is a journalist, New York Times contributor, swimmer, surfer, and the author of American Chinatown: A People's History of Five Neighborhoods, Why We Swim, and now On Muscle.

We all have those days where we'd rather just not. The ancients knew days like this.

Happy Earth Day! Let today be a reminder of how the Stoics looked to nature as a guide for living wisely and well.

Marcus Aurelius' life teaches us how to live well. And because he lived well, his story also teaches us how to die well: with grace, with strength, with empathy, and with the comfort of knowing that he lived a good life as a good man.

Last week, Rory McIlroy won the 2025 Masters Tournament, securing his first Green Jacket and completing the career Grand Slam. Nearly five years earlier, The Golf Channel profiled Ryan in a feature on Rory McIlroy, showing how 'The Obstacle Is The Way' helped Rory reset his mindset and fuel what would become one of the most remarkable comebacks in golf history.

When Marcus Aurelius addresses “you”—reminding you that your thoughts shape the quality of your mind, or advising you to choose not to be harmed so that you won't feel harmed—he is speaking to himself. This exercise in self-improvement is so sincere and earnest, sometimes painfully so, that it unintentionally speaks directly to us, helping us with our modern problems. In today's episode, Ryan Holiday shares the profound shift these lessons had on his life since discovering Meditations at 19.

What do an A-list actor, a four-star Navy admiral, and a world-famous magician have in common? Meditations by Marcus Aurelius has profoundly shaped each of their lives—proof that a Roman emperor's private reflections still resonate 2,000 years later.In today's episode, Ryan speaks with actor Patrick Dempsey, director Francis Ford Coppola, Professor Jennifer Baker, magician Derren Brown, bestselling author Donald Robertson, Admiral William McRaven, and voice actor/musician Troy Baker about their personal connections to Meditations.

The Stoics weren't just leaders and philosophers, they were also parents, spouses, and friends who experienced joy, who fell in love, who cherished the beauty of the world around them.

True fortune is not what happens to us, but how we choose to meet it.

There is almost no situation that hatred improves, but love enhances nearly everything.

In Meditations, Marcus Aurelius says, “Today I escaped from anxiety. Or no, I discarded it, because it was within me, in my own perceptions—not outside.” Today, bestselling author Chris Guillebeau joins Ryan to talk about the overwhelming anxiety that many experience when it comes to modern decision-making, time management, and ambition. They talk about the pressure of choosing the “right” next move, time blindness vs. time anxiety, strategies for managing calendar clutter, how Memento mori can be a tool for finding clarity and purpose, and more. Chris Guillebeau is the New York Times bestselling author of The $100 Startup, Side Hustle, and The Happiness of Pursuit, which have sold over one million copies worldwide. During a lifetime of self-employment that included a four-year commitment as a volunteer executive in West Africa, he visited every country in the world (193 in total) before his thirty-fifth birthday. In his latest book, Time Anxiety: The Illusion of Urgency and a Better Way to Live, Chris offers a bold path for redefining our relationship with the clock.Follow Chris on Instagram @193Countries and on X @chrisguillebeau. Check out his podcast the Side Hustle School and more of his work at chrisguillebeau.com

It should be the easiest book in the world to read. And yet…

When people show us who they are, we ought to believe them. They are the way they are—they have to be that way.

Saying no isn't selfish; it is a powerful act of self-respect. Listen to the audiobook of Stillness Is The Key narrated by Ryan Holiday on Audible: https://www.audible.com/

In today's Part 2 episode, award-winning author Daniel Pink joins Ryan to explore how fear of regret, awkwardness, and failure hold us back—and how embracing a 'shots on goal' mindset can be life-changing. Dan opens up about how he reframed a personal regret to shape his future choices, while Ryan shares what he sees as his own version of the infamous 'No Ragrets' tattoo.Daniel Pink is an award-winning author of five New York Times bestsellers, including his latest, The Power of Regret: How Looking Backward Moves Us Forward. His other books include the New York Times bestsellers When and A Whole New Mind — as well as the #1 New York Times bestsellers Drive and To Sell is Human. Follow Daniel on Instagram and X @DanielPinkSign up for Daniel's newsletter The Pink Report: https://www.danpink.com/

We must all see the pursuit of philosophy as both a mental and physical exercise. Mens sana in corpore sano—a strong mind in a strong body.

The way to understand and comprehend anything important is by doing the work. By going to the source. By returning over and over again, bringing new experiences, new questions, new contexts.

If it happened, then it was meant to happen.The great German philosopher Friedrich Nietzsche would describe his formula for human greatness as amor fati—a love of fate. “That one wants nothing to be different, not forward, not backwards, not in all eternity. Not merely bear what is necessary, still less conceal it….but love it.”

We must stand firm, unyielding in our refusal to compromise on what we know is right.

We all experience regret, but what if we could turn it into an advantage? Best-selling author Daniel Pink joins Ryan to reveal how regret isn't just a painful emotion—it's a powerful tool for growth, better decision-making, and a more fulfilling life. They talk about the challenge of juggling work and family, the surprising most common regrets people have, and the eye-opening data on how regret shapes our future.Daniel Pink is an award-winning author of five New York Times bestsellers, including his latest, The Power of Regret: How Looking Backward Moves Us Forward. His other books include the New York Times bestsellers When and A Whole New Mind — as well as the #1 New York Times bestsellers Drive and To Sell is Human.

The White Lotus season finale aired Sunday, titled "Amor Fati"—and without giving away any spoilers, it served as a powerful reminder of a timeless philosophy: to love one's fate.

It's a book that was never meant to be read. So why has Meditations by Marcus Aurelius endured and influenced across so many centuries? And what makes its ancient wisdom still relevant to the modern problems we face today?

Good exists everywhere—we need only look for it. Beauty surrounds us, waiting to be noticed.

In a note to himself in the early days of the pandemic, Ryan Holiday wrote, “2020 is a test: will it make you a better person or a worse person?” That was the test that he reminded myself of over and over again: will this make you a better person or a worse person?Check out the blog post of this episode: https://ryanholiday.net/

Does telling your story mean revealing everything? Bestselling author and viral poet Maggie Smith returns for part two of her conversation with Ryan, discussing how writers decide what to share and what to keep sacred. They debunk the myth that memoirs must be exposés, talk about the role of empathy in both storytelling and activism, and explore the challenges of staying true to one's work while navigating success.In 2016, Maggie Smith's poem Good Bones became a viral sensation. It was named the “Official Poem of 2016” by the Public Radio International. Maggie Smith is the New York Times bestselling author of You Could Make This Place Beautiful; My Thoughts Have Wings, a picture book illustrated by SCBWI Portfolio grand prize winner Leanne Hatch; the national bestsellers Goldenrod and Keep Moving: Notes on Loss, Creativity, and Change; as well as Good Bones, named one of the Best Five Poetry Books of 2017 by the Washington Post and winner of the 2018 Independent Publisher Book Awards Gold Medal in Poetry.

Want to jump on a quick call to chat? Should we have coffee next week? You got a few seconds? These may seem small, but they add up.

A lot of times discipline is pushing yourself to do something you don't want to do, but the other part of it—what we might call the temperance part—is not doing the stuff you do want to do.Ready to make real, lasting changes in your life? Our course Habits for Success, Habits for Happiness provides a proven framework to build and maintain positive habits that will transform your daily routines. Check it out here: https://store.dailystoic.com

The best Stoics did not simply accept the awfulness of their times or participate in the corruption. So how did they fight it? How did they get revenge on the bad guys?