The Daily Stoic

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.

As history repeats itself in new and unfamiliar forms, we will once again choose to stand firm, knowing that while the storm may be relentless, our resolve will always be stronger.

Most of our problems are not so urgent. The stakes are not so high. Yet we rush, we react emotionally. But how much more magnanimous and wise it would be to wait. To think. To calm down.

During the month of October in America, images of death are all around us as we celebrate Halloween—and while it’s a playful time of year, it’s also an opportunity to practice memento mori, a reminder to treat our time as a gift.⏳ Get your own Memento Mori Premium Signet Ring | https://store.dailystoic.com/

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.

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

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?

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?

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 Wellma

If you need money and success to live well, then you’re vulnerable to things not going well.

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.

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.

Some people travel for the food. Others for the nightlife. Some travel for work. Others travel to get away. Ryan travels for the swimming.

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/

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.

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!

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://w

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.

What matters is how we bring the show to a close, what matters is the ending we give each scene.

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.