Wisdom Takes Work: Ryan Holiday on What AI Can’t Teach You

The James Altucher Show

James Altucher

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4.6 • 2.7K Ratings

🗓️ 11 November 2025

⏱️ 63 minutes

🔗️ Recording | iTunes | RSS

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Summary

A Note from James:

Wisdom Takes Work is Ryan Holiday’s fourth book exploring the Stoic virtues, and this time he’s taking on the big one — wisdom. His earlier books on courage, temperance, and justice were all great conversations, but this one hit me personally. I’ve often thought I had wisdom, only to realize later that I didn’t — or at least not as much as I thought.

Ryan’s writing blends ancient Stoic philosophy with modern life in a way that feels both practical and timeless. We talked about how wisdom isn’t something you possess; it’s something you practice. It’s not about having all the answers — it’s about asking better questions, learning through experience, and staying humble enough to admit what you don’t know. Ryan’s back on the show — probably more than any other guest — and each time, I walk away seeing the world differently.

Episode Description:

James sits down with bestselling author and Stoic philosopher Ryan Holiday to discuss Wisdom Takes Work, the newest addition to his series on the cardinal virtues. Together they unpack what “wisdom” really means — not as a static trait, but as an ongoing practice of curiosity, humility, and doing hard things.

The conversation ranges from the limits of AI (“great at knowledge, terrible at wisdom”) to the importance of reading history, counting names on a plaque instead of trusting bad data, and learning by doing. Ryan also shares new insights from his upcoming biography of Admiral James Stockdale, and how the act of challenging himself as a writer mirrors the Stoic pursuit of wisdom itself.

What You’ll Learn:

Why wisdom isn’t about knowing — it’s about learning, questioning, and doing.
How AI amplifies knowledge but can’t replace human judgment or discernment.
Why experience, pain, and humility are necessary ingredients for growth.
How Ryan’s research on Admiral Stockdale is changing his approach to writing and life.
Practical ways to cultivate wisdom — from reading and travel to mentoring and open-mindedness.

Timestamped Chapters:

[00:00] Introduction: The difference between knowledge and wisdom
[02:54] A Note from James — Why wisdom is the hardest virtue
[05:37] AI’s limits and the danger of overconfidence
[08:57] “Wisdom takes work”: Stoic principles in action
[11:35] The verbs of virtue — acting with courage, justice, and discipline
[13:12] Ryan’s AI experiment and the Naval Academy plaque
[16:10] Knowing what you don’t know — humility as wisdom
[18:30] Parenting, ego, and learning to argue less
[22:00] Why age doesn’t guarantee wisdom
[25:10] The trap of resisting change and staying “the smartest person in the room”
[27:00] Adapting to new generations and ideas
[31:00] Is wisdom a talent or a learned skill?
[34:00] How books and mentors shape a wise mind
[37:00] Raising curious kids in the age of MrBeast and AI
[40:20] Teaching curiosity and lifelong learning
[42:25] Practicing wisdom: reading, travel, and mentorship
[47:00] Learning by doing — the pain and reward of hard work
[50:20] Writing, research, and the lesson of David McCullough
[53:07] Why Ryan’s next book is his hardest yet — Admiral Stockdale’s story
[55:50] Finding new mentors and growing past your comfort zone
[57:14] Living the Stoic life — success, service, and perspective

Additional Resources:

Ryan Holiday – Wisdom Takes Work
Ryan Holiday’s other Stoic virtue books:

Courage Is Calling

Discipline Is Destiny

Right Thing, Right Now

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Transcript

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0:00.0	How's the business going?
0:01.1	We're busier than ever, but struggling to get the staff we need. Oh, recruiting can be such a distraction. We gave Job Centre Plus a try, and they've really helped us out. Really? Yeah. It was dead easy. We got our own employer advisor, Julie, who helped advertise our jobs, shortlisted candidates for us and letters interview at the Job Centre. We've hired some great people, and Job Centre Plus really took the hassle out of it, And there was no fee.
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0:25.9	business.gov.com.uk slash recruit. Eligibility criteria apply. Today on the James Altiger
0:32.7	show. I've worked in the AI space for 35 years in one way or the other.
0:38.9	So I'm a huge opponent.
0:39.8	But this is the one area where AI is a tool and not the leader, which is wisdom.
0:45.9	AI is really good at knowledge.
0:47.9	It's really good at helping you find knowledge.
0:50.5	It can even give you knowledge.
0:52.5	But it certainly can't give you wisdom.
0:54.0	And doing something with knowledge as opposed to just... It can even give you knowledge, but it certainly can't give you wisdom.
1:06.4	And doing something with knowledge as opposed to just memorizing it is the difference between accumulating facts, which I'll say is the AI world, and wisdom, which is the domain of humans.
1:10.2	All of the virtues have to be seen as verbs and not nouns.
1:12.5	Like, you don't have courage.
1:14.2	You have to act with courage.
1:16.1	Discipline is a thing that you do.
1:20.1	Justice is a thing that you give, not a thing that you get.
1:25.8	This isn't your average business podcast, and he's not your average host.
1:28.2	This is the James Altasier show.
1:40.0	Wisdom takes work.
	...

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