The Daily Stoic – “Sit Down With Walter Isaacson and Ryan Holiday”
Podcast Date: December 21, 2025
Host: Ryan Holiday
Guest: Walter Isaacson

Episode Overview

In this engaging, wide-ranging conversation, bestselling author and Stoic advocate Ryan Holiday sits down with acclaimed biographer Walter Isaacson at the Texas Tribune Festival in Austin. While ostensibly an interview with Holiday, the discussion quickly becomes a collaborative exploration of Stoicism, southern novelist Walker Percy, the ripple effects of virtue across generations, how philosophical frameworks endure in turbulent times, and the modern relevance of the Stoic mindset for tackling both personal and societal challenges. The two discuss the evolution of Stoicism, its interplay with Christianity and American thought, the pitfalls of success and power, and how core virtues hold practical value in contemporary life—especially for leaders, creators, and anyone seeking meaning.

Key Discussion Points & Insights

1. Walker Percy and the Southern Stoic Tradition

[07:44–11:33]

• The conversation opens with deep appreciation for Walker Percy, particularly his novel The Moviegoer, and how Stoic ideas filter through Percy’s literary family tree.
• Holiday describes buying The Moviegoer in New Orleans and finding Stoic philosophy embodied in fiction for the first time.
  • “It was the first time I saw [the Stoics] in fiction. …It’s obviously the fictional take on the Stoics in Walker Percy’s [work].” (08:10)
• Isaacson highlights the inadequacies of both Stoicism and religion in Percy’s view—how characters strive for spiritual meaning after tragedies, showing the ongoing “search.”
• The discussion draws parallels between literary searching and contemporary yearning for meaning, noting that old-fashioned virtues can seem outdated yet still offer guidance.

2. Holiday’s Personal Path to Stoicism

[11:33–16:55]

• Holiday describes his college introduction to Marcus Aurelius’ Meditations as a catalyst for his philosophical journey.
  • “I didn’t know what I thought philosophy was, but I didn’t think it was the Emperor of Rome talking to himself about getting up early.” (11:44)
• Discussion on virtues: courage, discipline, justice, wisdom; Stoicism as a framework for staying good and focused in a chaotic world.
• Isaacson probes Holiday's transformation from a marketing professional disillusioned with media manipulation to author and advocate for Stoic values.

3. From Book to Daily Practice and Empire

[16:55–19:41]

• Holiday recounts pitching his publisher on Stoicism (“obscure school of ancient philosophy”) post-marketing career, the lukewarm reception, and how the success of The Obstacle Is the Way spawned a larger movement.
• Origins of The Daily Stoic book and newsletter—modeled after Tolstoy’s Calendar of Wisdom and Peter Drucker’s page-per-day format.
• He stresses the ongoing, daily nature of Stoic practice:
  • “Stoicism isn’t this philosophy that you read. It’s a philosophy I think you have to be reading.” (18:40)

4. How Stoicism Has Changed Holiday

[19:41–21:44]

• Early attraction to the “muscular” side of Stoicism—discipline, courage—but discovery that Stoicism centers on ethics, justice, and the common good.
• Holiday highlights Marcus Aurelius’ insistence on working with others for the public good, not succumbing to cynicism:
  • “You can’t let them suck you down…your job is to work with them and do your job.” (20:28)

5. What Stoicism Is—and Isn’t

[24:25–25:47]

• Holiday summarizes Stoicism as founded on accepting what you cannot control and responding virtuously to events:
  • “We don’t control what happens. We control how we respond to what happens.” (24:36)
• Clarifies Stoicism is not about emotionlessness, but pausing before responding, ensuring emotional responses do not dictate actions.

6. Stoicism’s Evolution & Its Parallels with Other Philosophies

[25:47–30:13]

• Isaacson and Holiday trace the journey of Stoicism from Greece to Rome, its absorption into Christianity, and its later rediscovery during the Enlightenment and Victorian era.
• Reflection on how Stoic virtues dovetail with Christian virtues, but differ in motivation—Stoicism as self-governed logic vs. religious commandment.
  • “Instead of saying, ‘God wants you to do this…’ it’s argument about your purpose and your meaning, but it’s less metaphysical.” (30:02)

7. Virtue, Fulfillment, and Public Life

[30:13–31:11]

• Stoicism is framed as both a path to virtue and fulfillment—but not one designed for ease.
  • “It is not designed for a life of ease…The Stoics saw philosophy as a pursuit in whatever calling or domain you happen to be operating in.” (30:19, 30:28)

8. Stoicism vs. Religion/Spirituality & Deism

[31:11–32:34]

• The Stoics believed in gods, but with an understanding that fate is indifferent—aligning at times with Deist thought prominent among U.S. founders.
  • “If there is a God, it is fundamentally indifferent to you. …You do everything you can, and…outcome is ultimately not up to you.” (31:57, 32:21)

9. Core Stoic Sayings and Practical Lessons

[32:34–38:04]

• “The obstacle is the way.” Marcus Aurelius’ insight is explained as a universal maxim for turning impediments into opportunities (35:18–35:23).
• Three favorite Stoic teachings highlighted:
  • Epictetus: “It’s not things that upset us, it’s our opinion about things.” (35:49–36:38)
  • Seneca: “Death is now. …The time that passes now belongs to death.” (36:42)
  • Aurelius: “Be careful not to be imperialized or stained purple”—don’t let power corrupt character; stay anchored in philosophy despite success. (37:28–38:04)

10. Stoicism, Power, and Elon Musk

[38:21–45:02]

• Reflection on Elon Musk as a modern, flawed Stoic figure: remarkable intellect and achievement, yet vulnerable to being “stained purple” by success and isolation.
• Isaacson and Holiday discuss Musk’s identification with Stoicism (“He’s a fan of yours, even if it’s not fully mutual” [39:52]), the dangers of the “demon loop/demon mode,” and how unchecked algorithmic environments can corrupt wisdom.
  • “How does someone become…changed by power, wealth, isolation, the algorithm…If it can happen to him, what chance do the rest of us have?” (39:28–39:44)

11. The Four Cardinal Virtues in a Modern, Tech-Driven World

[43:38–50:21]

• Holiday explains how courage, discipline, justice, and wisdom are as relevant as ever, especially in the age of AI and accelerating information.
  • “Wisdom is…what unlocks all the others.” (45:02)
• Isaacson draws parallels to the Founders, especially Franklin as emblematic of wisdom and the value of personality and warmth amidst genius.
• Dialogue emphasizes balance:
  • “All the virtues sit as a midpoint between two vices.” (48:48, Holiday quoting Aristotle)
  • “That’s something we’ve lost today—the notion that balance is the key to things, that going way out with any particular virtue can be a flaw.” (50:05, Isaacson)

Notable Quotes & Memorable Moments

• Ryan Holiday on Stoic Practice:
  “For me, the writing is my philosophical practice. …I take a thing from the Stoics every day and try to arrange it in a format that would make sense to me or someone that reminds me of something that either I need to know or I think people need to know.” (18:40)
• Walter Isaacson on Franklin vs. Musk:
  “To the extent [Franklin] had a flaw, it’s what you consider his virtue—he was so eager to make everybody like him…Empathy is not your friend, [according to Elon Musk].” (48:10)
• Ryan Holiday on Musk:
  “I like to write about dead people—it’s easier.” (39:56)

Timestamps for Major Segments

• [07:44] – Introduction & Walker Percy’s role in Stoic tradition
• [11:44] – How Holiday discovered Stoicism
• [16:03] – From marketing disillusionment to writing about philosophy
• [18:37] – The daily ritual and the growth of The Daily Stoic
• [19:41] – How Stoicism changed Holiday personally
• [24:25] – What is Stoicism? (Definition & misconceptions)
• [25:47] – Stoicism’s historical transmission and intersection with Christianity
• [31:11] – Stoicism, faith, and deism
• [32:34] – Stoic sayings explained (The Obstacle Is the Way, etc.)
• [38:21] – Applying Stoicism to Elon Musk and modern challenges
• [43:38] – The four cardinal virtues in the digital age
• [46:36] – Wisdom and learning from history
• [48:10] – Individual founders’ virtues and the need for balance in life
• [50:05] – Moderation and the dangers of extreme virtue

Episode Tone and Atmosphere

• Warm, intellectually stimulating, and accessible, with moments of humor (especially regarding writing about living vs. dead billionaires).
• Both guests balance scholarly analysis with relatable anecdotes and practical application, while keeping the discussion grounded amid reflections on family, failure, and the challenges of modern life.

For those interested in Stoicism, history, or just finding ways to cope with chaos and temptation in the modern world, this episode is a generous, insightful distillation of philosophy-in-action, articulated by two of this era’s most thoughtful writers.