Risk-taking means diving into the unknown, which is scary because anything could happen, but not taking risks is the only guarantee that nothing will change. That’s what Chase Jarvis is here to talk with Ryan about in today’s episode, as his latest book, Never Play It Safe, is a guide for anyone looking to overcome fear around the unknown, trust their intuition, and become comfortable taking the uncomfortable risks in order to get to where they want to go. Chase talks to Ryan about managing risks when pursuing creative projects, balancing urgency with long-term thinking, the necessity of constraints in fostering creativity, maintaining personal and artistic authenticity, and the role of intuition and wisdom in achieving a well-lived life. Chase is an acclaimed artist, photographer, entrepreneur, podcast host of The Chase Jarvis LIVE Show, and author of Creative Calling and Never Play It Safe. You can follow Chase on Instagram , YouTube, and X @ ChaseJarvis and check out his websiteWatch Ryan’s first appearance on The Chase Jarvis Live Show back in 2012 for Trust Me, I’m Lying: https://www.youtube.com/watch?v=odfH7LZwAQ8Listen to Chase’s podcast: The Chase Jarvis LIVE Show🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

We can flatter ourselves that we’re essential, that we’re one of the good guys, that we’re preventing things from being worse. But are we? Or is that just what we want to believe?📕 Pick up a signed copy of Right Thing, Right Now by Ryan Holiday | https://store.dailystoic.com/📓 Grab your own leather bound signed edition of The Daily Stoic! Check it out at the Daily Stoic Store: https://store.dailystoic.com/📚 Check out Dying Every Day: Seneca at the Court of Nero by James Romm at The Painted Porch | https://www.thepaintedporch.com/✉️ 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.

Destiny taps each of us on the shoulder, will we be able to answer? Will we have cultivated the skills and virtues necessary to answer well? That’s what philosophy is about—preparing you for whatever fortune has in store, big and small.Ask DS: What is the Stoic way to process and receive compliments? What is Ryan’s advice to stop obsessing over what could go wrong? How did the Stoics approach parenting and creating a generational impact?🎙️ Listen to Francis Ford Coppola’s  interview on the Daily Stoic | Apple Podcasts &  Spotify🎥 Watch Francis Ford Coppola’s interview on YouTube 🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

If you need money and success to live well, then you’re vulnerable to things not going well.💡 The Wealthy Stoic: A Daily Stoic Guide to Being Rich, Happy, and Free explores how stoic ideas can be applied to personal finance, wealth-building, financial mindset, and how it can help you overcome common financial obstacles and challengesGet The Wealthy Stoic: A Daily Stoic Guide to Being Rich, Happy, and Free & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

Today, the tables have turned as Ryan Holiday is interviewed by his research assistant, Billy Oppenheimer, to talk about the 10th Anniversary Edition of The Obstacle Is the Way. They discussed why Ryan felt it was important to update and expand the book, what stories and pieces of wisdom were necessary to add, and the experience as a writer of revisiting material you wrote 10 years ago. Ryan also touched on the evolving reception of Stoicism and how his perspectives and writing style have changed in the process, providing a deeper understanding of how life's obstacles present us an opportunity for virtue as much as victory.Billy Oppenheimer is Ryan Holiday’s research assistant and the writer behind the newsletter, Six at 6 on Sunday. To read more of his work, check out his website billyoppenheimer.com.📕 Get a signed, numbered first-edition of the 10th anniversary edition of The Obstacle Is the Way by Ryan Holiday at dailystoic.com/obstacle✉️ 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.

So much has changed over the course of a decade…so little as well. The 10th anniversary edition of The Obstacle Is the Way has relevant and insightful lessons (including a new foreword) that Ryan couldn’t have possibly written a decade ago. If you have been listening to the podcast for a while but haven’t read The Obstacle Is the Way yet, this is a fantastic time and place to start—it will advance your understanding of the lessons of the Stoics and how to apply them to your life.📕 Get a signed, numbered first-edition of the 10th anniversary edition of The Obstacle Is the Way by Ryan Holiday at dailystoic.com/obstacle✉️ 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.

The Stoics—just like activists—didn’t always win but they showed themselves always as worthy of winning. They showed themselves to be the most disciplined side.🎙️ Listen to Thomas Rick’s interview on the Daily Stoic📚 Grab a copy of Waging a Good War by Thomas Ricks at The Painted Porch https://www.thepaintedporch.com/ 📕 You can get signed copies of Ryan's books: Discipline is Destiny , Courage is Calling, & Right Thing, Right Now at https://store.dailystoic.com/📓 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/🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

A lot can change in 10 years, yet The Obstacle Is the Way remains the timeless formula for turning our toughest trials into our greatest triumphs. 📕 Get a signed, numbered first-edition of the 10th anniversary edition of The Obstacle Is the Way by Ryan Holiday at dailystoic.com/obstacle✉️ 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.

In Meditations, Marcus Aurelius wrote “You could leave life right now. Let that determine what you do and say and think.” Death is inevitable for all of us and practicing the art of Memento Mori reminds us to live each day to the fullest and with virtue. David Kessler, a grief and loss expert, joins Ryan today to talk about why a meaningful life comes from embracing rather than fearing death, how grief can shape our understanding and appreciation of life, the balance between grief and joy, and how losing his son changed everything he thought he knew about grief. David’s personal experience with grief started very young, as a child witnessing a mass shooting while his mother was dying in a hospital. For most of his life, David has taught physicians, nurses, counselors, police, and first responders about the end of life, trauma, and grief. Even after years of studying grief and counseling those experiencing it, his life was turned upside down by the sudden death of his twenty-one-year-old son.David co-authored two books with Dr. Elisabeth Kubler-Ross, including On Grief and Grieving, and after experiencing the death of his son, he updated her 5 stages of grief with a 6th stage: meaning. 📚 Grab signed copies of Finding Meaning and the Finding Meaning Workbook by David Kessler at The Painted Porch https://www.thepaintedporch.com/ Go to griefbook.com and follow David Kessler on Instagram and X | @IAmDavidKessler 📕 Our favorite translation of Seneca’s essays on grief and loss, Hardship and Happiness (The Complete Works of Lucius Annaeus Seneca) is available at The Painted Porch | https://www.thepaintedporch.com/🪙 Designed with the intention of carrying them in your pocket, our Memento Mori Medallion is a literal and inescapable reminder that “you could leave life right now.”Check it out at https://store.dailystoic.com/See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We don’t have the power to bring the people we love back, but by choosing to embody the virtues of loved ones we have lost, we not only carry forward their spirit in our actions, we transform our pain and suffering into meaning and purpose.🎙️ Listen to Francis Ford Coppola’s interview on the Daily Stoic | Apple Podcasts &  Spotify🎥 Watch Francis Ford Coppola’s interview on YouTube 📓 Grab your own leather bound signed edition of The Daily Stoic! Check it out at the Daily Stoic Store: https://store.dailystoic.com/🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

The annoying coworker, the unreasonable client, the demanding coach, the selfish teammate, the family member who pushes all your buttons—these are constant opportunities to practice virtue. Ask DS: What is the purpose of our ego? How can we find a balance between confidence and humility? + More! 📕 Get a signed, numbered first-edition of the 10th anniversary edition of The Obstacle Is the Way by Ryan Holiday at dailystoic.com/obstacle🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

We carry our own weight in this world, we blow our own nose, as Epictetus says. It’s what’s right, it’s what’s fair, it’s our job.💡 We designed The Daily Stoic Leadership Challenge: Ancient Wisdom For Modern Leaders to mirror the kind of education that produced historically great leaders like Marcus Aurelius. Check it out at store.dailystoic.comGet The Daily Stoic Leadership Challenge: Ancient Wisdom For Modern Leaders & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

Brigid Delaney was at a unique point in her life and found herself looking for answers around life’s deepest questions: What does it mean to be a good person? How do we stop letting the things out of our control rule our emotions? Can our anger be tamed? After learning more about Stoicism, Brigid decided to let the ancient wisdom from Marcus Aurelius, Epictetus, and Seneca guide her decisions for a year. While in Australia on tour, Ryan had the chance to meet Brigid in person and talk with her about why Stoicism resonated with her, how to successfully apply Stoicism to modern problems, and the common misconceptions around Stoicism being exclusively for men. To learn more about Brigid’s experience, check out her book Reasons Not to Worry: How to Be Stoic in Chaotic Times. Brigid Delaney is the author of Reasons Not to Worry: How to Be Stoic in Chaotic Times and Wellmania: Extreme Misadventures in the Search for Wellness. Be sure to check out the Netflix series Brigid co-create, inspired by her book Wellmania!📚 Books Mentioned: Reasons Not to Worry: How to Be Stoic in Chaotic Times by Brigid Delaney The Obstacle Is the Way by Ryan HolidayOn Anger: De Ira by SenecaThe Therapy of Desire by Martha Nussbaum Dying Every Day: Seneca at the Court of Nero by James RommFollow Brigid Delaney on X @ BrigidWD🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

What matters is how we bring the show to a close, what matters is the ending we give each scene. 📕 Pick up a copy of Lives of the Stoics by Ryan Holiday | https://store.dailystoic.com/📚 Dying Every Day: Seneca at the Court of Nero by James Romm at The Painted Porch https://www.thepaintedporch.com/ 🎙️Listen to James Romm’s interview on the Daily Stoic✉️ 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.

It wasn’t fun that it went sideways. It hurt that they hurt you. It took something that you can never get back. That’s life. That’s resiliency. That’s how the obstacle is the way.📕 Get a signed, numbered first-edition of the 10th anniversary edition of The Obstacle Is the Way by Ryan Holiday at dailystoic.com/obstacle📓 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/🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

Some people travel for the food. Others for the nightlife. Some travel for work. Others travel to get away. Ryan travels for the swimming.🎙️ Listen to Bonnie Tsui’s interview on the Daily Stoic Podcast📚 Grab a copy of Swimming Holes of Texas by Julie Wernersbach | https://www.thepaintedporch.com/🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

Wright Thompson grew up in the Mississippi Delta, unaware that his family farm was just 23 miles away from the barn where 14 year old Emmett Till was murdered in 1955. When writing The Barn, Wright had to take a look at the place he had always known as home with fresh eyes and courageously uncover the details of Emmett's tragic story that had been buried for decades. In today’s episode, Wright and Ryan continue their conversation about Emmett Till’s legacy, the complexity of American history, why it’s important to know where you come from, and the responsibility of preserving Emmett’s story. You can get signed copies of The Barn and Wright’s other books,The Cost of These Dreams, Pappyland, at The Painted Porch | https://www.thepaintedporch.com/You can follow him on Instagram @wrightthompsonbooks or head to his website, https://wrightthompson.com/🎙️ Listen to Pt. 1 of Wright and Ryan’s conversation on the Daily Stoic | Apple Podcasts &  SpotifyCheck out Wright Thompson’s very first interview on the Daily Stoic Podcast | Apple Podcasts, Spotify, or watch it on YouTube!🎥 Subscribe to 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.

None of us own anything. Everything is constantly in flux. What we have today may be gone tomorrow. 📓 Grab your own leather bound signed edition of The Daily Stoic! Check it out at the Daily Stoic Store: https://store.dailystoic.com/🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

A lot has happened in the 10 years since The Obstacle Is the Way came out. Ryan is a different person, a different writer, than he was back in 2014 and he was so excited to get a chance to improve and update this book accordingly. There were mistakes to fix, criticism to address (some not so fun), and new ideas to incorporate.📕 Get a signed, numbered first-edition of the 10th anniversary edition of The Obstacle Is the Way by Ryan Holiday at dailystoic.com/obstacleAsk DS: Does Ryan have a meditation practice that helps him achieve stillness?How do you measure if you’re happy with effort over the outcome? How do you maintain the virtue of justice without over giving or self-sacrificing? 🎟 Ryan Holiday is going on tour! Grab tickets for London, Rotterdam, Dublin, Vancouver, and Toronto at ryanholiday.net/tour✉️ 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.

Anne Frank and Martin Luther King Junior were born in the same year. The last known widow of a Civil War veteran lived to see Barack Obama become the first African-American President. Emmett Till would be the same age as Neil Diamond, Martha Stewart, and Bob Dylan in 2024 if he was not brutally tortured and murdered in 1955. Facts like these remind us that history is not as far away as we think it is. Wright Thompson, is a Senior Writer at ESPN and author of The Cost of These Dreams, Pappyland, and most recently, The Barn, which uncovers the real story of Emmett Till’s murder in the Mississippi Delta. Wright joins Ryan to talk about the impact of cognitive dissonance, how political rhetoric has shaped racial violence, why history is closer than we think, the rise and fall of the cotton boom, and what it was like for Wright to learn the truth about Emmett Till’s story. You can get signed copies of The Barn and Wright’s other books, The Cost of These Dreams, Pappyland, at The Painted Porch | https://www.thepaintedporch.com/You can follow him on Instagram @wrightthompsonbooks or head to his website, https://wrightthompson.com/🎙️Listen to Wright Thompson’s first interview on the Daily Stoic Podcast | Apple Podcasts, Spotify, or watch it on YouTube!🎥 Subscribe to 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.