The Daily Stoic

Great leaders don’t just build winning teams, they build people who can go on to lead without them. In today’s episode, Ryan talks about the idea of “growing a coaching tree” and what it means to create a culture that outlasts you. Using the San Antonio Spurs as a real-life example, Ryan looks at how the best leaders teach, empower, and develop others, not just for their own success, but for the success of everyone who comes next.

In honor of Mother’s Day, Ryan talks with Donald Robertson about the powerful influence Marcus Aurelius’ mother had on his life and philosophy. Even though Stoicism is usually talked about as a philosophy shaped by men, Marcus’ mother may have been his first and most important model of Stoic character, shaping the virtues he would spend his life trying to practice.Donald Robertson is a writer, cognitive-behavioral psychotherapist and trainer. He is a Fellow of the Royal Society for Public Health (RSPH). Donald specializes in teaching evidence-based psychological skills, and is known as an expert on the relationship between modern psychotherapy (CBT) and classical Greek and Roman philosophy.Listen to the full episode with Donald Robertson: Apple Podcasts, Spotify, YouTubeSubstackX: @donjrobertsonIG: @donaldjrobertson

Jon Gustin got sober at the beginning of 2023, but as he explains in today’s episode, getting sober was not the end of the struggle. It was the beginning of finally facing everything he had spent years avoiding. Jon talks with Ryan about his unhealthy relationship with substances, the emotional rock bottom that forced him to change, and the daily practices that helped him stay sober and focus on being a better husband and father. 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.

Cato’s life was his philosophy, and the Stoics never stopped looking to his example. In today’s episode, Ryan explores why Cato the Younger became one of Stoicism’s most admired figures, and what his life can teach us about courage, character, and standing for what’s right. 

These are impersonal forces. This is fortune and fate. It’s not targeting you. It’s not favoring or picking on you. 

Arete. To the Greeks, it meant excellence. It was the ultimate expression of human greatness—moral, physical, spiritual. It’s what the Stoics were chasing. It’s what you’re chasing today. But how do we get there?

They’re awful. They’re frustrating. They need to be stopped. These are the people who take up so much space in our head.

You think you want more freedom, but too much of it can work against you. In this episode, Ryan talks with David Epstein about why constraints can actually make us better. They discuss how deadlines sharpen focus, why too much autonomy can become a trap, and why “freedom within a framework” may be more useful than total freedom.David Epstein is the author of the #1 New York Times best seller Range: Why Generalists Triumph in a Specialized World. His third book, Inside the Box: How Constraints Make Us Better, is out now!

The terrible diagnosis. The betrayal. The broken heart. Are they Stoics really saying you should love that? Is that what it means to “amor fati”—to love your fate?

Recognizing your anger in the moment, feeling it rising before it takes over, means you’ve already started mastering it.

You think you’ve read Meditations, but the deeper truths in Marcus Aurelius’ private writings often reveal themselves only after years of revisiting them. In this episode, Ryan shares the hidden lessons he missed on his first, second, and even tenth read and why this book keeps giving you new insights even years later.

What happens after you survive something that should have killed you? After being critically injured in Afghanistan, Kyle Carpenter faced years of surgeries, setbacks, and a future he couldn’t yet see. In Part 2, Ryan and Kyle talk about learning to embrace the struggle, ask for help, and keep going when the path forward is unclear.Kyle Carpenter is a medically retired United States Marine who received the United States' highest military honor, the Medal of Honor in 2010. Kyle is the youngest living Medal of Honor recipient. 

When we stop resisting and start learning, the obstacle becomes the way.

Watch Ryan's response on The Daily Stoic YouTube channel here: https://www.youtube.com/watch?v=h1OfTQusvYM

Dr. Edith Eger faced the worst humanity can do, survived Auschwitz, and went on to build a 98-year life rooted in resilience, forgiveness, and meaning. In this episode, Ryan reflects on her life and lessons as a Holocaust survivor, student of Viktor Frankl, and a powerful voice on resilience and forgiveness.

The surprising thing about all this is that you were surprised. How could you not have seen this coming?Reading Marcus Aurelius can change your life, but only if you know how to read his work

To wrap up Meditations Month, today Ryan explores Marcus’s best rules for using the precious time in your life.Reading Marcus Aurelius can change your life, but only if you know how to read his work

The Medal of Honor is the highest military award in the United States, given for extraordinary courage in the face of danger. In this episode, Ryan sits down with Kyle Carpenter, the youngest living recipient, to talk about what that kind of courage really looks like and what comes after it.Kyle received the Medal of Honor after throwing himself on a live grenade to save a fellow Marine in Afghanistan. It was a split second decision that changed his life. But as he explains, that moment was only the beginning.Kyle Carpenter is a medically retired United States Marine who received the United States' highest military honor, the Medal of Honor in 2010. 

You can’t learn history that you don’t take the time to look at, that you think you already understand.

It was a dark world…and Marcus Aurelius desperately needed some light.LAST CHANCE | Your ticket to the live Q&A with Ryan Holiday