The Daily Stoic – "Your New Stoic Role Models for a Stronger Life"

Date: December 24, 2025
Host: Ryan Holiday
Guests: Michelle "Mace" Curran, Nick Thompson, Rutger Bregman, Billy Oppenheimer

Episode Overview

In this special compilation episode, Ryan Holiday explores the four cardinal Stoic virtues—Courage, Discipline, Justice, and Wisdom—through candid conversations with four modern role models. Drawing on their life experiences, personal stories, and practical applications, the episode demonstrates how ancient Stoic principles remain urgent and actionable in everyday life. Each segment zooms in on a virtue through the lens of a remarkable guest:

• Fighter pilot Michelle Curran on Courage
• CEO and marathoner Nick Thompson on Discipline
• Historian and activist Rutger Bregman on Justice
• Writer and research assistant Billy Oppenheimer on Wisdom

Through real stories and honest discussions, listeners are invited to reflect on how these virtues can serve as guides and sources of strength in challenging moments.

Key Discussion Points & Insights

Introduction: Everyday Examples of the Virtues (05:10–08:55)

• Ryan shares a personal story: A tense encounter with a neighbor's car nearly clipping him while walking his dog. He reflects on how both his own and the driver's reactions illustrated aspects of the Stoic virtues—discipline in not escalating, courage in facing the situation, justice in the neighbor’s apology, and wisdom in learning restraint.
  • "A lack of restraint, lack of discipline on my part, that was like part of the inciting incident here. The willingness to make amends or admit error, right? That's what my neighbor illustrated there..." – Ryan Holiday [07:09]
• Framing: Virtue isn't only about grand acts—it's woven into small, everyday decisions.

Section 1: COURAGE with Michelle "Mace" Curran (08:55–21:21)

Michelle Curran: Former Air Force F-16 solo pilot, lead solo for the Thunderbirds, author of "The Flip Side"

Key Takeaways

• The Golden Mean and Real Courage:
  • Ryan: "Courage is not the opposite of cowardice. It's in the middle between recklessness and cowardice... Confidence is somewhere in the middle of those two extremes." [09:09–09:36]
  • Michelle illustrates the lesson with her "call sign" story—pushing herself nearly to black out on a training flight due to ego and the fear of looking weak.
    • "I was so worried about failing that. That was more important to me than my physical safety." – Michelle Curran [11:43]
    • "The irony of course is that you did look really stupid." – Ryan Holiday [11:54]
• Vulnerability and Asking for Help:
  • Ryan references Marcus Aurelius: "If you’re all storming a wall and someone falls, you're not like, you idiot. In fact, they're like, there's something beautiful about being able to help that person." [13:12]
  • Michelle: "When I was flying for the Thunderbirds... I'd be like, I'm not brave. Like, I've had so much self doubt. I've had so many moments of fear, I just forge ahead anyway. And it was never about what they thought I was being brave for..." [13:57]
  • Ryan: "But that is the definition of bravery though. If you're not afraid, then it's not brave." [14:17]
• The Unseen Side of High-Performance Careers:
  • Reality vs. pop culture myths (i.e., Top Gun): Long hours, discomfort, constant setbacks—real courage lies in enduring the grind, not just performing on "game day."
  • "If it was glamour, if the practice was fun, more people would do it." – Ryan Holiday [18:10]
• Process over Outcome:
  • Loving the process (writing, flying, training) rather than just the rewards or recognition is essential to long-term courage and continued growth.

Section 2: DISCIPLINE with Nick Thompson (22:39–28:02)

Nick Thompson: CEO of The Atlantic, elite marathoner, author of "The Running Ground"

Key Takeaways

• The Generational Loop of Discipline:
  • Nick reflects on how his complicated relationship with his father shaped his own drive and work habits.
  • "I try very hard not to let my discipline drop, in part because I don't want to be that." – Nick Thompson [23:29]
• Running as a Discipline Metaphor:
  • Running every day builds "cumulative" discipline, spills into other areas (work, writing).
  • "If you do a hard thing first thing in the morning, it's easy to do the next hard thing... the focus required for running helps you with everything else." – Nick Thompson [24:13–24:34]
• Incremental Progress Over Time:
  • "If you run every day and if you run hard from time to time, you get faster. It just happens." – Nick Thompson [25:22]
  • Often the improvements aren’t perceptible day-to-day, but accrue over time through consistent effort—a core Stoic lesson.
• Writing and Running Parallels:
  • Breaks down complex, long-term projects (like books or races) into manageable daily tasks.
  • "You just do it a little bit here, you do it a little bit there, and like, it gets done right. Eventually it's done right." – Nick Thompson [26:13]

Section 3: JUSTICE with Rutger Bregman (28:02–41:24)

Rutger Bregman: Dutch historian, co-founder of the School for Moral Ambition, author of "Moral Ambition"

Key Takeaways

• Justice Is Action, Not an Inheritance:
  • "You're not born as a good person. You become a good person by doing good things. So just get started." – Rutger Bregman [29:11]
• Inclusive Movements & Coalition Building:
  • Ryan highlights how the most powerful social movements (abolition, suffrage) succeeded through broad coalitions—not purity or exclusion.
    • "When you decline an alliance with someone, you are often forcing them to ally with your opponents." – Ryan Holiday [30:29]
    • "If someone agrees with you for like 70 to 80% of the time, that person is an ally, not your enemy." – Rutger Bregman [31:20]
• The Power of Perseverance and Legacy:
  • The long timeline of social change; most originators of major reforms died before seeing victory but inspired future movements.
  • "Knowing that you're part of something that's much bigger than you are, that gives me a lot of energy to work on that stuff." – Rutger Bregman [35:13]
• Justice as the Core Purpose of Strength and Virtue:
  • "All the other virtues are rendered meaningless if not directed at justice." – Ryan Holiday [40:23]
  • "So, yeah, justice has to be the thing that your life is." – Ryan Holiday [41:17]
  • Stoic justice is local and practical—how you pay, treat, and interact with those around you.

Section 4: WISDOM with Billy Oppenheimer (43:59–56:40)

Billy Oppenheimer: Writer, research assistant, author of the Six at Six newsletter

Key Takeaways

• Wisdom as a Process, Not a Destination:
  • Ryan discusses how writing each book in his Virtue series came at exactly the right moment to apply its teaching to his own life—wisdom, especially, is ever-relevant as life changes.
  • "Who I would be four, five years later, I would have more to say about it... some of the thoughts on education and setting up an education would be more relevant to me." – Ryan Holiday [45:11]
• No Shortcuts to Wisdom:
  • Seneca’s story of the Roman who employed slaves to memorize books for him as an early example of seeking shortcuts—an allegory for "outsourcing" wisdom, now echoed in modern AI and tech.
    • "Seneca is laughing about how, you know, it's not something anyone can do for you and there's no shortcuts. And he says, you know, no one was ever wise by chance. Like, no one's beaten the system, basically." – Ryan Holiday [48:01]
  • True wisdom is developed through effortful engagement, ongoing learning, and self-reflection—not by collecting facts or finding hacks.
• On Learning & Education:
  • The never-ending nature of education, both personal and for one's children—the "best way" is a perennial struggle.
    • "If you think it's too late, you don't understand what wisdom is. Like, it's an ongoing pursuit." – Ryan Holiday [56:23]
  • Timeless wisdom about education—principles over formats or systems, openness to new methods.

Notable Quotes & Memorable Moments

• On Courage

  • "If you're not afraid, then it's not brave." – Ryan Holiday [14:17]
  • "I was so worried about failing that that was more important to me than my physical safety." – Michelle Curran [11:43]

• On Discipline

  • "If you do a hard thing first thing in the morning, it’s easy to do the next hard thing." – Nick Thompson [24:13]
  • "It’s this cumulative gain... block by block." – Ryan Holiday [25:30]

• On Justice

  • "You're not born as a good person. You become a good person by doing good things." – Rutger Bregman [29:11]
  • "All the other virtues are rendered meaningless if not directed at justice." – Ryan Holiday [40:23]

• On Wisdom

  • "No one was ever wise by chance." – Seneca (quoted by Ryan Holiday) [48:10]
  • "If you think it's too late, you don't understand what wisdom is. Like, it's an ongoing pursuit." – Ryan Holiday [56:23]

Important Timestamps

| Timestamp | Segment / Topic | Speaker(s) | |-----------|------------------------------------------|-----------------------------| | 05:10 | Introduction & Everyday Virtue | Ryan Holiday | | 08:55 | COURAGE | Michelle Curran, Ryan Holiday | | 22:39 | DISCIPLINE | Nick Thompson, Ryan Holiday | | 28:02 | JUSTICE | Rutger Bregman, Ryan Holiday| | 43:59 | WISDOM | Billy Oppenheimer, Ryan Holiday | | 56:40 | Conclusion, reflections on education | Ryan Holiday |

Final Thoughts

Throughout the episode, Ryan Holiday and his guests illustrate that Stoic virtue is less about attaining a singular heroic status and more about how we respond, adapt, and persist in ordinary and extraordinary circumstances alike. Their lived experiences highlight that courage, discipline, justice, and wisdom are forged and revealed through daily trials, tough questions, and a willingness to learn and grow.

For listeners seeking practical, relatable inspiration to build a "stronger life," these new role models, and the virtues they embody, offer a clear and actionable path forward.

Podcast: The Daily Stoic – "Your New Stoic Role Models for a Stronger Life" – December 24, 2025