Podcast Summary:

The Bulwark Podcast | Ryan Holiday: Life Is Too Short to Be a Bootlicker
Date: October 24, 2025
Host: Tim Miller
Guest: Ryan Holiday, writer/philosopher, author of "Wisdom Takes Work"

Episode Overview

This episode takes a step back from the frenetic political news cycle to explore deeper themes of stoic philosophy, personal courage, and the dilemmas of living in a turbulent political era. Host Tim Miller is joined by Ryan Holiday, bestselling Stoic writer, for a candid, wide-ranging conversation. They discuss current political challenges, the dangers of sycophancy and authoritarianism, the importance of self-reflection, the impact of information diets, and how stoic wisdom can guide us through personal and collective storms.

Key Discussion Points & Insights

1. Redistricting and Political Power Plays (00:00–13:00)

• Tim Miller begins with an analysis of political developments in redistricting, affecting Democrats' prospects in 2026 and 2028.

  • Virginia's redistricting could net Democrats three new seats.
  • Mike Pence’s behind-the-scenes efforts could halt GOP gerrymandering in Indiana.
  • The potential overturning of the Voting Rights Act may have less immediate midterm impact than feared.
  • Other states (e.g., Colorado, Illinois, Maryland) have varying opportunities and challenges in redistricting.
  • Miller emphasizes the strategic imperative for Democrats to win the House in 2026 to safeguard democracy, especially against rising authoritarian threats associated with Trumpism.

• Steve Bannon's Provocative Trump 2028 Claims (06:05+):

  • Bannon asserts publicly that “Trump is going to be President in 2028.”
  • Miller unpacks Bannon’s intention: attention-seeking and narrative control rather than divulging a serious plot.
  • He stresses the strategic response: Democrats and pro-democracy forces must focus on attainable levers of power—not fall for psychological manipulation.

  "This is an angle. This is a bit. He wants attention for himself." – Tim Miller (06:07)

  • Mocking the concept of an octogenarian Trump as king can be a useful counter-strategy.

2. The Timelessness of Bootlicking & The Lessons from Stoicism (13:00–21:05)

• Ryan Holiday joins, and is asked about the daily experience of hearing extreme pro-Trump sycophancy.

  • Ryan draws parallels between today’s political bootlickers and ancient court sycophants — referencing Seneca flattering Nero as a survival strategy.

    "The lengths that humans will go to degrade themselves to maintain their access and influence." (16:42)

  • He notes the enduring pattern of power and its tendency to breed insincere flattery and self-degradation among courtiers.
  • Miller and Holiday reflect on the societal regression to "royal court" behaviors of subservience.

• On Personal Integrity & Stoic Opposition:

  • Ryan: "Life’s too short to be a bootlicker." (18:12)

  • He recounts the ancient Stoic ‘red thread’ metaphor: be yourself, don’t mute your identity even in the face of power.

    "Everyone else can be the white threads. I prefer to be the red thread in the garment that makes it beautiful." – Ryan Holiday paraphrasing Agrippinas (18:39)

  • He asserts that confronting aspiring autocrats demands wisdom, ethics, and courage — even at personal or professional risk.

3. The Navy Lecture Controversy: Courage, Cowardice, and Cancel Culture (21:05–30:28)

• Background:
  Holiday describes being uninvited from delivering his annual U.S. Naval Academy lecture after refusing to omit slides about banned books, including a Maya Angelou title, and the importance of engaging with uncomfortable ideas.

• Institutional Fear:

  • The Academy caved to political pressure, fearing both government reprisals and right-wing outrage.
  • Holiday points out the real motive for cancellation wasn’t controversy per se, but "very real reprisals from people in power" (26:15).

    "It’s not like the carrot and the stick. It’s two sticks." (27:27)

• The Folly of Appeasement:

  • Compromising with authoritarians only invites more pressure, not protection.

    "When you compromise with an extortionist, you just get more pressure and extortion." (28:36)

• Hypocrisy of Free Speech Advocates:

  • Miller and Holiday note the lack of support from right-wing "cancel culture" critics who remained silent.

4. Wisdom, Self-Deception, and the Dangers of Contrarian Success (32:34–39:19)

• Holiday’s New Book:

  • The theme is the battle against the "fool within and without".

  • True wisdom isn’t just knowledge, but actively suppressing foolish impulses, bias, and self-deception.

    "Wisdom isn’t just this kind of acquisition of knowledge and facts... a big part of it is just keeping that stupid part of yourself in check." – Ryan Holiday (32:34)

• Cautionary Tales: Elon Musk and Peter Thiel

  • Miller and Holiday discuss how extraordinary success (e.g., Elon Musk, Peter Thiel) can foster ego-driven self-destruction.

  • The victory of a risky contrarian bet warps future judgment, causing one to ignore legitimate warning signs.

    "Making a contrarian bet that turns out to be right can be a brain-destroying experience." – Ryan Holiday (36:01)

  • Trump is also cited: the surprise 2016 win taught him to disregard all dissent – with disastrous results.

  • The discussion covers the social echo chambers of the powerful, and how unchallenged ideas among elites (e.g., at dinner parties) escape into the mainstream, sometimes with dangerous consequences.

    "They get used to trotting things out in these dinners... then when it emerges in public, it’s subjected to the marketplace of ideas, where it is swiftly dismantled and destroyed." – Ryan Holiday (42:53)

5. The Information Diet: Trump, Us, and Everyone in Between (45:01–55:33)

• Media Diet & Presidential Responsibility:

  • The dangers of "media brain rot"—Trump’s habit of obsessively watching television news, illustrated by anecdotes of Trump being too easily accessible to D-list celebrities and swayed by cable news cycles.
  • Leaders require reflection, not immersion in "artificial, radically cranked up versions of reality." (46:51)

• Our Own Media Consumption:

  • Miller pivots to listeners’ habits: Many anti-Trumpers are just as trapped in echo chambers as Trump’s Fox News-addicted base.

  • Holiday urges consuming less real-time commentary, more rigorous and challenging content.

    "Podcasts are not a substitute for thinking... Most people are consuming way too much real time information and way too much commentary, and they’re not consuming enough biography, history, psychology, philosophy. Like... read a fucking book." – Ryan Holiday (53:15)

• Embracing Discomfort:

  • Both advocate consuming news and perspectives that occasionally unsettle: "If you’re only consuming information that makes you comfortable, that’s a problem." (55:39)

  • Holiday shares a personal lesson: learning to challenge his own conservative upbringing by reading critiques, which burst the bubble of absolute certainty.

6. Reaching Young Men: History, Philosophy, and Political Engagement (57:30–65:19)

• Stoicism’s Appeal to Men:

  • Miller notes the Roman Empire fascination among straight men—and their increasing alignment with Trump (57:30).

  • Holiday says Democrats have vacated the cultural ground young men care about (history, self-help, sports, comedy), leaving it to right-wing influencers.

    "If your world doesn’t include people that are into self-help and into history and into comedy and sports, like you’re living in the most abnormal world there is." (58:30)

  • There’s a "huge gap in the market" for content that affirms mainstream values and connects via shared interests. Democrats should engage rather than sneer at these entry points.

• The Power of History for Norms and Values:

  • History provides nonpartisan context for current political crises, helps clarify why Trump’s actions are so shocking to those who know the backstory, and supplies narratives that reinforce civic virtues.

  "So much of what Trump is doing is shocking and appalling... But if you don’t have the historical basis, you’re not going to know that." – Ryan Holiday (63:28)

Notable Quotes & Memorable Moments

• On Bootlicking and Courage:
  “Life’s too short to be a bootlicker.” – Ryan Holiday (18:12)

• On Wisdom and Self-Control:
  "Wisdom isn’t just this kind of acquisition of knowledge and facts... a big part of it is just keeping that stupid part of yourself in check." – Ryan Holiday (32:34)

• On the Dangers of Contrarian Success:
  "Making a contrarian bet that turns out to be right can be a brain-destroying experience." – Ryan Holiday (36:01)

• On Authoritarian Appeasement:
  "When you compromise with an extortionist, you just get more pressure and extortion." – Ryan Holiday (28:36)

• On Information Diets:
  "Podcasts are not a substitute for thinking... read a fucking book." – Ryan Holiday (53:15)

• On the Power of Unchallenged Elites:
  "They get used to trotting things out in these dinners... then when it emerges in public, it’s subjected to the marketplace of ideas, where it is swiftly dismantled and destroyed." – Ryan Holiday (42:53)

Timestamps for Key Segments

• 00:00–13:00: Miller’s political dispatch: redistricting, Trump 2028, defensive strategies for democracy
• 13:01–21:05: Bootlickers, Stoic philosophy, ancient vs. modern courtier culture
• 21:05–30:28: Ryan Holiday’s Naval Academy "canceling" story, courage under political pressure, hypocrisy of cancel culture critics
• 32:34–39:19: Wisdom, battle with the fool inside, Elon Musk, Peter Thiel, dangers of unchecked ego
• 39:19–43:56: Dinner-party echo chambers, how unchecked power/wealth isolates, spreads fringe ideas
• 45:01–47:47: Trump’s disastrous information diet, why real leaders need better sources and boundaries
• 47:47–53:04: Resistance echo chambers, warning to listeners about falling into the same traps, call to intellectual humility
• 53:04–55:33: The need for brain-challenging, uncomfortable information, media literacy tips
• 57:30–65:19: History, masculinity, how the left can reach young men, restoring civic values, and the limited appeal of exclusively partisan narratives

Conclusion

The episode closes with Miller and Holiday reflecting on the enduring wisdom of history, the importance for individuals—and political movements—to confront uncomfortable truths, and the need to cultivate moral courage in times of stress. Holiday’s call to "be the red thread" serves as both a challenge and a message of hope for listeners yearning for sanity, decency, and clarity amidst political and cultural turbulence.

For more from Ryan Holiday:

• Book: Wisdom Takes Work
• Website: DailyStoic.com
• Podcast: The Daily Stoic
• Bookstore: Painted Porch, Bastrop, TX