The Breakfast Club — Interview with Ryan Holiday: "Wisdom Takes Work"

Podcast: The Breakfast Club (iHeartPodcasts)
Date: October 27, 2025
Host(s): DJ Envy, Jess Hilarious, Charlamagne Tha God, Lauren LaRose
Guest: Ryan Holiday
Episode Theme: The importance of wisdom, how to cultivate it, and its place as the capstone of the four cardinal virtues in Stoic philosophy—discussing Ryan Holiday’s new book, Wisdom Takes Work: Learn, Apply, Repeat.

Overview

In this episode, The Breakfast Club welcomes back bestselling author and modern Stoic Ryan Holiday to discuss his latest book, Wisdom Takes Work: Learn, Apply, Repeat. Holiday delves into the notion that wisdom is the virtue upon which all other virtues depend, arguing that genuine wisdom is earned through continual effort and reflection. The discussion explores how to cultivate wisdom in an age overrun by information, distraction, and anti-intellectual trends; it also touches on how wisdom interacts with courage, discipline, justice, and the realities and dangers of neglecting it today.

Key Discussion Points

1. Wisdom as the Keystone Virtue

• Ryan Holiday: “The four virtues of Stoic philosophy...are courage, discipline, justice and wisdom. They're all separate, but...wisdom tells us when and how to apply the others. It doesn't matter how good your heart is if you don't have the wisdom, the intelligence to know how to bring it into the world.” (03:05)
• Wisdom is what enables good intentions, courage, and justice to be applied effectively.
• Smart people can make foolish decisions without wisdom or self-awareness.

2. Wisdom Is Not Guaranteed By Age or Experience

• Challenging clichés like “wisdom comes with age.”
• Ryan Holiday: “I met a lot of dumb old people too.” (03:42)
• Life offers lessons constantly, but ignoring them means consequences grow more severe.
• Holiday: "When we're late to learning lessons, that doesn't just affect us, but...the people who...bear the consequences of that...painful lesson that we chose to learn the hard way." (05:34)

3. Learning: School, Experience, Mentorship

• Debate about the value of college and formal education versus real-life learning and apprenticeships.
• Ryan Holiday: “I'm a proud college dropout...I met Robert Greene, our mutual friend, and then I realized that's what I wanted to do...I'm a big believer in apprenticeships and mentorships. You got to find your teachers.” (08:15–09:42)
• Importance of self-direction, using available resources (like the campus library!), and real-world mentors.
• “There's a difference between school and education.” (08:15)

4. The Digital Age: Chatter vs. Thought

• Social media incentivizes reaction, not reflection.
• Holiday: “Social media is by definition talking and not listening....We have this enormous sort of media culture that's about chatter and noise and it's not about thoughts and reflection.” (11:16)
• Lack of historical context makes people vulnerable to manipulative figures and misinformation.
• On demagogues: “The idea of the demagogue, the idea of the strongman, the idea of the con man is as old a thing as there has ever been.” (12:24)

5. Second Brain and Information Diet

• Charlamagne: “What's a second brain?” (13:44)
• Holiday: Keeping organized notes and records of what you’ve learned is crucial: “How are you collecting and organizing this information?...If you're not keeping a journal, if you're not recording the information that you're consuming or learning, where's it going?” (13:46)
• Filtering what you consume is vital: “What are you eating? What are you consuming?...People just consume straight garbage...you definitely see this on the right, this just sort of depraved garbage information diet of the worst slop and nonsense.” (14:48)
• The dangers of overconsumption—even of real-time news and social media.

6. Can Wisdom Protect You From Influence & Misinformation?

• Lauren LaRose: Can wisdom shield you from being unduly influenced by the sheer volume of digital information? (22:57)
• Holiday: “You want to be one of the people that's not up for grabs...I know what's what. I know what humans are. I know how humanity works. I know history...We can all be made fools and suckers, but the bigger basis protects you against the day to day barrage.” (23:11)

7. Cultivating Wisdom Requires Work & Struggle

• Wisdom takes effort—mental struggle, reading, reflection, recognizing and challenging your biases.
• Holiday: “It is struggle. It's a battle. It's a battle against ignorance, it's a battle against misinformation, it's a battle against your own biases....Your mind is not always your friend.” (26:36)
• Learn, Apply, Repeat: Stay curious, never stop being a student.
• Story about Marcus Aurelius attending philosophy lessons even as the most powerful man in Rome.

8. Wisdom and Today’s Political Climate

• Recent censorship and anti-intellectual trends—example of canceled Naval Academy lecture.
• Holiday: “I can't get up there and give a lecture about wisdom as they're literally removing books from a library.” (29:30)
• Coining “kakistocracy” — rule by the stupidest — as a diagnosis for much of today’s political class.
• Holiday: “People who are not just not smart, but actively afraid of and angry at and resentful of people who have competence and knowledge because they're fundamentally threatened by it.” (31:40)

9. The Importance of Negative Capability and Real Listening

• Balancing conflicting ideas—knowing when to revise or hold onto an opinion.
• Holiday: “Negative capability is the idea: Can you hold two opposing ideas in your head? So on the one hand, the experts are wrong a lot. On the other hand, expertise is still really important.” (33:43)
• In dialogue, value curiosity and humility—especially in diverse settings.
• “Resilient people...understand that people feel differently about different things, have different opinions about different things, and to be interested and curious about that without necessarily changing your mind all of the time.” (35:02)

Notable Quotes and Memorable Moments

• Holiday: "Wisdom is the sort of piece that brings it all together...one of the problems is that we assume wisdom is this thing that just happens...It's no guarantee. I met a lot of dumb old people too." (03:42)
• Lauren: “I completely agree that wisdom is a lost art. I think you have a lot of smart people. I don't think you have a lot of wise people nowadays.” (04:34)
• Holiday: “It's not just knowing that book banning is stupid and reckless and dangerous. But then I have to decide, do I want to preserve my access or do I want to say what I think is true?” (29:30)
• Charlamagne: "You really know people that think chocolate milk come from a black house brown cow." (24:19)
  Holiday: "That is a statistical fact. It is nuts. That is like, is that 20%? It's like 20%." (24:24)
• Holiday: “If you don't have some sense of wisdom, some sense of knowledge, you're gonna be vulnerable to a thing [AI] that, by the way, hallucinates a significant percentage of the time.” (25:20)
• Holiday: “Your mind is not always your friend....Ego being another one that gets in the way of us learning and seeing what we need to see.” (26:36)
• On Marcus Aurelius: "Here we have the philosopher king still taking up his tablets and going to school. But that's why he was a philosopher king." (27:54)
• Holiday: “Diversity is strength in the sense that you want to bring as many different opinions...but at the end of the day, you do have to decide what you think, what you feel, what you're gonna do. Especially in a position of leadership.” (35:02)
• Charlamagne (humorously): “Next time, bring some chocolate milk from a brown cow.” (36:42)
  Holiday: “I do have a brown cow. It does not make chocolate milk.” (36:45)

Timestamps for Key Segments

• 03:05: Ryan Holiday explains why wisdom is the foundation for other virtues.
• 05:34: On learning from experience, and why wisdom is not guaranteed with age.
• 08:15–09:42: Ryan discusses alternative paths to education and mentorship.
• 11:16: Social media’s incentives and the decline of reflective discourse.
• 13:44–14:48: “Second brain” and curation of one’s information diet.
• 22:57–23:11: Wisdom as protection from undue influence and misinformation.
• 26:36: The practical work and struggle of cultivating wisdom.
• 29:30–31:40: Political censorship, anti-intellectualism, and courage.
• 33:43: Balancing skepticism about "experts" with valuing credentials and experience.
• 35:02: The art of listening in diverse or opposing company.

Conclusion

The episode offers an accessible, honest, and urgent exploration of why wisdom matters now more than ever, how it’s cultivated through a lifetime of learning and humility, and why it needs to stand as a bulwark against both daily information overload and the anti-intellectual trends shaping politics and culture. Packed with practical advice, real-world anecdotes, and humor, this is a must-listen for anyone striving to think deeply and live wisely in chaotic times.