Podcast Summary: The Daily Stoic

Episode: Everything (And I Really Mean Everything) Is A Chance To Do This
Host: Ryan Holiday
Date: November 2, 2025

Overview of the Episode

In this weekend edition episode, Ryan Holiday delivers a deep reflection on a foundational Stoic theme: “the obstacle is the way.” Revisiting Marcus Aurelius' famous passage, Holiday explores how life’s adversities—big and small—are always opportunities to practice the core virtues of Stoicism. Rather than seeing obstacles solely as chances for professional or personal gain, he suggests the Stoics saw them, above all, as chances to become better, more virtuous people. Drawing on personal anecdotes, historical examples, and a moving interview segment with filmmaker Francis Ford Coppola, Holiday underscores how even life’s most heartbreaking trials can become prompts for courage, justice, discipline, and wisdom.

Key Discussion Points and Insights

Rethinking “The Obstacle Is The Way”

• Early Interpretation: Holiday recalls initially reading Marcus Aurelius’ message as “any obstacle can be turned into an advantage,” particularly professional or personal success (05:00).
  • Example: Entrepreneurs thriving in downturns, athletes bouncing back from injury.
  • Famous quote: “What stands in the way becomes the way.”
• A Deeper Reading: Over time, Holiday comes to see that the Stoics’ insight is not to glibly suggest every setback is a boon.
  • Quote: “It would be insane, to say nothing of insulting and insensitive, to tell someone that their terminal cancer was an advantage.” (06:55)
  • The true lesson: Adversity always provides a chance for practicing virtue—responding well, not just “winning.”

The Four Stoic Virtues

• Defining Virtue: Holiday outlines Zeno’s four Stoic virtues (07:45):
  • Courage: Bravery, fortitude, honor, sacrifice.
  • Discipline (Temperance): Self-control, moderation, equanimity.
  • Justice: Fairness, honesty, service, kindness.
  • Wisdom: Knowledge, truth, self-reflection, discernment.
• Quote: “Marcus Aurelius calls these four virtues the touchstones of goodness.” (08:22)

Applying Virtue in Life’s Hardest Moments

• Not Only For Triumphs: Even crushing setbacks or grief—loss, illness, betrayals—can be transformed by how we respond (08:50).
• Story of Francis Ford Coppola: The filmmaker shares how Stoic wisdom helped him cope with losing his wife of 60 years (09:48).
  • Coppola Quote: “You lose a loved one, honor her, and in a sense, try to be more like her, and then she'll live in your actions... And I just try to be like her.” (09:55)
  • Following his late wife’s example by reaching out to others in loneliness or suffering.

Ryan’s Personal Anecdotes

• Life’s Relentless Obstacles: Holiday reflects on a decade filled with rewarding moments and serious setbacks—pandemics, natural disasters, professional crises, family issues (11:00).
  • “There were funerals and late-night phone calls with news you don’t want to get…It was just life, right? Life is not easy. Life does not go the way we want it to go.” (11:54)
• Internal Challenge: He describes how he imposed on himself a Stoic test during the pandemic: “2020 is a test. Will it make you a better person or a worse one?” (13:00)

Practicing Virtue: An Ongoing Craft

• Virtue in Good Times and Bad: Stoicism is about maintaining virtue not only through adversity but also in times of abundance—demanding humility, discipline, and generosity (15:35).
• Wisdom as Meta-Virtue: It’s wisdom that guides us in knowing which virtue is most needed in a given moment and striking the right balance (16:45).
• Virtue as Practice: “Virtue wasn’t a thing that you’re born with, it was a kind of craft, a thing that you get better at as you go. Aristotle says we become builders by building and we become harpists by playing the harp. Similarly, we become just by doing just actions, temperate by doing temperate actions, and brave by doing brave actions.” (18:19)

Notable Quotes & Memorable Moments

• On the core Stoic lesson:

  “There’s not always a chance to make more money or to win an election, but there is always a chance for you to grow and change and practice virtue.”
  (07:22, Ryan Holiday)

• Francis Ford Coppola on grief and virtue:

  “You lose a loved one, honor her…try to be more like her, and then she’ll live in your actions. My wife was very good…and so I started to do that—call them up and say, ‘How are you?’ And they were so pleased. I keep my wife in my life with Marcus Aurelius’ advice by trying to be more like her.”
  (09:55, Francis Ford Coppola)

• On the ongoing nature of virtue:

  “Virtue isn’t something that you ever finish or take leave of... the more we think about virtue, the more we apply it, the better we become. Not just creatively, but personally.”
  (17:30, Ryan Holiday)

• On control:

  “That’s the one part of life that we control. And that’s what Stoicism is ultimately about—responding well to life, to the world, to unpredictability, to setbacks, to injustices.”
  (19:30, Ryan Holiday)

Timestamps for Important Segments

• 05:00 – Revisiting and re-evaluating “the obstacle is the way”
• 07:45 – Defining the four cardinal Stoic virtues
• 09:48 – Francis Ford Coppola shares how Stoic advice helped him in grief
• 11:00 – Holiday’s personal and professional setbacks
• 13:00 – The pandemic as a Stoic test of character
• 15:35 – The demands of virtue in good times as well as bad
• 16:45 – Wisdom as the guiding meta-virtue
• 18:19 – Virtue as practice and craft

Tone and Original Language Notes

Ryan Holiday’s tone is candid, humble, and reflective—sometimes confessional. He is direct about his own misreadings and missteps, and shares personal stories with the same openness he brings to philosophical ideas. The brief appearance by Francis Ford Coppola adds a moving, personal voice to the conversation, using everyday language to convey profound emotion and wisdom.

Final Reflection

This episode encourages listeners not to see Stoicism as a strategy for turning every negative into a worldly win, but as a call to answer adversity with virtue—always available, always within our power, no matter the external outcome. Holiday's evolving understanding of Stoic wisdom makes this an especially thoughtful and relatable listen for anyone facing life’s inevitable difficulties.