Why Writing the Stockdale Biography Challenges Ryan

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

• Admiral James Stockdale – U.S. Naval Academy Biography
• Robert Caro – Working: Researching, Interviewing, Writing
• David McCullough – Truman and John Adams
• Ryan Holiday’s The Daily Stoic Podcast – Spotify

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