The Daily Stoic – BONUS | Where Service Meets Stoicism — Joe Byerly & Ryan Holiday
A conversation about wisdom, leadership, writing, and growth
Published: November 13, 2025

Main Theme & Purpose

This episode features a rich, behind-the-scenes discussion between NYT bestselling author Ryan Holiday and retired Army Lieutenant Colonel Joe Byerly. Drawing from Holiday’s new book Wisdom Takes Work, their own writing collaboration, and Byerly’s military leadership experience, the two explore how the lifelong pursuit and practice of wisdom is inextricably tied to service, reflection, writing, and self-examination. Listeners get a firsthand look at Holiday’s research/writing process, the value of skepticism and curiosity, and why the hard, unglamorous work of distilling experience into wisdom can’t be shortcut.

Key Discussion Points & Insights

1. The Ongoing Pursuit of Wisdom

• Wisdom as a Process
  Holiday emphasizes wisdom is not a fixed asset but “has to be earned… not something you’re born with, and not something anyone can give you. Wisdom is the result of hard work” (14:12, Ryan Holiday).

• The Evolving Horizon
  Wisdom isn’t a destination but an endless pursuit: “It’s like the horizon. You can make progress towards it, but it also gets further away.” (14:39, Holiday).

• Area Specific and Fleeting
  Even those considered wise may only have expertise in certain areas, and “the possession of it is fleeting at best” (14:33, Byerly).

2. Defining and Recognizing Wisdom

• Humility Over Intelligence
  Wealth, status, and intelligence aren’t reliable proxies for wisdom; humility, open-mindedness, and continual learning matter far more (15:38–16:20).
  Memorable line: “There are many smart people who are fundamentally foolish. And then there are very many people who no one would define as well educated, but are in fact quite wise” (16:18, Holiday).

• Examples of Wisdom and Its Pitfalls

  • Michel de Montaigne—self-education and perpetual curiosity
  • Abraham Lincoln—self-taught, putting wisdom into transformational action
  • Elon Musk—a case study in how untempered intelligence can turn “dangerously stupid” without grounding or humility ([19:10], Holiday):

    “He’s both one of the smartest people in the world and one of the most dangerously stupid people in the world… How does this person, who goes from reading Soviet rocket manuals, go to retweeting misinformation from Russian bots?”

3. The Value of Writing: Thinking with Your Fingers

• Writing Clarifies and Deepens Thought

  • Stories of Eisenhower, Thomas Merton, General Mattis, and Eric Hoffer reinforce the value of writing to process, test, and clarify beliefs.
  • “Thinking with your fingers… is, to me, one of the best ways to clarify your thoughts and to get them there. One of the things I don't like about podcasts is it's a lot of bullshitting. It’s a lot of first takes, and your first take is very rarely a good one” (29:02, Holiday).
  • Joan Didion: “Writing is a hostile act” in the sense that you must fully persuade and refine your thoughts for an imagined reader (31:28).

• Note-taking and Synthesis
  Both guests share their notecard/notebook methods.

  “Notebooks are a way of remembering who you used to be. It's also a way of remembering what you used to know... It's a gift to your future self” (56:14–56:44, Holiday).

• Recall, Reflection, and Use

  • The habit of writing, organizing, and revisiting notes builds greater recall and an internalized “second brain,” which is invaluable for leadership and decision-making (47:55–48:20, Byerly & Holiday).

4. The Danger of Shortcuts and the Importance of Discernment

• AI, Misinformation, and Critical Thinking

  • AI can quickly produce plausible-sounding but deeply flawed answers; a wise person is one who can “spot bullshit” and isn’t satisfied with surface-level explanations (37:43–42:11, Holiday).
  • Anecdote: Holiday’s attempts to use AI to research Naval Academy WWII casualties revealed AI’s “persuasive but fundamentally wrong” logic.

• Curiosity and the Will to Dig Deeper

  • “Curiosity… not being satisfied with the first answer is a big part of it” (42:11–42:15, Byerly).
  • The process of pulling on threads often reveals much more beneath the surface, both in research and life.

• Building Our Beliefs with Quality Materials

  • Byerly’s “walls we build” metaphor:

    “All across the Internet, there are people just handing bricks out… if you’re not careful, algorithms are going to build the wall… and you’re going to have a belief system that’s built on a bunch of shitty bricks” (36:55–37:43, Byerly).

5. Leadership, Communication, and the Modern World

• Leaders Must Write and Communicate Clearly
  “If you're not starting from a point of clarity and conciseness… it's going to get real sloppy real fast… The ability to get your thoughts on paper and explain something… that is the skill” (33:53–34:11, Holiday).

• Critical Reading Is as Important as Writing
  Wisdom also means being able to recognize “bad writing, bad thinking, manipulative arguments—and insufficient logic in others’ communication.” (35:13–36:07, Holiday).

• Systems for Capturing Wisdom
  Whether three-ring binders, note cards, or digital files, it’s less about the method and more about building a personal system of learning (George Raveling, General Mattis, Da Vinci all used their own systems—45:25–46:12).

6. The Writer’s (and Researcher’s) Apprenticeship

• Learning in Public & From Others

  • Byerly reflects on going from military command to writing apprentice, and the continuous cycle of learning new skills.
  • Holiday explains how his process has evolved—becoming more rigorous, drawing on a wider array of sources, deeply challenging his own first instincts:

    “I feel like the ground that I’m standing on has gotten firmer because I’ve asked that of myself… at some point, you get to a place where you can just smell what you’re looking for, like a shark can smell blood in the water” (64:00–65:10, Holiday).

• Mentorship and Delegation

  • The process of seeking, testing, and delegating research—learning when to trust your own instinct and when to push further is key to both writing and leadership (66:06–67:13, Holiday/Byerly).

7. Personal Growth and Takeaways

• Service and Humility

  • Both men discuss the value of serving others—whether soldiers, readers, or history itself—and the humbling experience of always being a beginner.

• Wise Communication in a Hostile World

  • Holiday: “It’s not just what you say, but how what you say makes people feel… I’m trying to be a bit more thoughtful and deliberate, especially in this fragile, sensitive/inflammatory world we’re living in. You just don’t do yourself any favors posting or saying the first thought that pops into your head.” (70:09–70:41)

  • Byerly references Ben Franklin: “The ultimate goal is to do so in a way where [wisdom] will be received.” (71:37-71:51).

Notable Quotes & Memorable Moments

• “Wisdom is the result of hard work. It’s something that ensues as a result of a relatively timeless and unchanging process.” (14:12, Ryan Holiday)
• “Curiosity… not being satisfied with the first answer is a big part of it, too.” (42:15, Byerly)
• “Just not falling for bad thinking, sloppy thinking, manipulative thinking, propaganda, etc., is just a big part of being a wise person.” (41:50, Holiday)
• “Not writing prose, but reading the book and then the note cards of it… there needs to be some process by which you record and synthesize the information.” (43:31, Holiday)
• “Notebooks are a way of remembering who you used to be. It’s also a way of remembering what you used to know. It’s a gift to your future self.” (56:44, Holiday)
• “There’s something about wisdom that is one, fundamentally about humility, and two, something very different than success, power, wealth.” (16:08, Holiday)

Timestamps for Important Segments

• 08:28 — The writing life: balancing past, present, and future projects
• 14:12–15:39 — Defining wisdom and its elusive nature
• 19:10–20:10 — Musk as both an inspiring and cautionary tale
• 29:00–33:06 — Writing as an act of refinement, empathy, and leadership
• 36:55–37:43 — The “walls we build” metaphor for belief formation & dangers of information shortcuts
• 41:30–42:11 — The challenge of spotting BS in the AI era
• 47:55–48:20 — Personal note-taking and its lifelong value
• 56:14–56:53 — The time-travel of notetaking: a “gift to your future self”
• 70:09–71:51 — Social intelligence, deliberate communication, and the importance of being received

Tone and Style

The conversation is candid, reflective, and instructional, blending the humility and seriousness of two lifelong students of wisdom with numerous practical examples and moments of humor. Both speakers offer concrete anecdotes while frequently acknowledging their own learning curves, mistakes, and the ongoing, unfinished nature of their quest.

For Listeners:

This episode offers an immersive journey into the philosophy and mechanics of wisdom—not as a lofty ideal, but as a hands-on practice embedded in writing, leadership, learning, and the humility of constantly questioning even your own best ideas. Whether you’re a writer, leader, or simply someone striving to grow, the episode’s lessons are as actionable as they are timeless.