Wisdom Takes Work: Ryan Holiday on What AI Can’t Teach You
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this episode of The James Altucher Show, bestselling author Ryan Holiday returns to discuss his new book "Wisdom Takes Work," the fourth installment in his series on Stoic virtues. (02:57) Holiday and Altucher explore what distinguishes wisdom from mere knowledge, particularly in the age of AI. They delve into why artificial intelligence excels at providing information but falls short when it comes to true wisdom, which requires experience, humility, and the willingness to do hard things. The conversation ranges from parenting challenges to the importance of reading history, with Holiday sharing insights from his research on Admiral James Stockdale for his upcoming biography. (35:37) Throughout their discussion, they emphasize that wisdom isn't something you possess but rather something you practice through continuous learning, questioning, and embracing discomfort.
- Main theme: The distinction between knowledge and wisdom, and how to cultivate wisdom through deliberate practice and lifelong learning
Speakers
Ryan Holiday
Ryan Holiday is a bestselling author who has written more than ten books on Stoicism, including the widely acclaimed series on the four cardinal virtues. His books have sold over 10 million copies in 30+ languages, establishing him as one of the foremost modern interpreters of ancient Stoic philosophy. Holiday operates a popular bookstore outside Austin, Texas, hosts The Daily Stoic podcast, and speaks regularly to corporations and organizations about applying Stoic principles to modern life.
James Altucher
James Altucher is an entrepreneur, author, podcaster, and chess master who hosts The James Altucher Show. He has started multiple companies and written numerous books on entrepreneurship, investing, and personal development. Altucher is known for his candid discussions about failure, success, and the practical application of wisdom in business and life.
Key Takeaways
Wisdom Requires Active Practice, Not Passive Accumulation
Holiday emphasizes that all virtues, including wisdom, must be seen as verbs rather than nouns. (11:19) You don't "have" wisdom like a possession - you must actively practice it through continuous learning and application. The subtitle of Holiday's book, "Learn, Apply, Repeat," captures this essential process. This means constantly questioning your assumptions, seeking new perspectives, and remaining humble about what you don't know. Unlike knowledge, which can be accumulated and stored, wisdom emerges from the ongoing process of engaging deeply with ideas and experiences over extended periods of time.
AI Excels at Knowledge but Cannot Provide Wisdom
While AI is excellent at finding and organizing information, it fundamentally cannot provide wisdom because wisdom requires human judgment, experience, and the ability to say "I don't know." (05:27) Holiday illustrates this with an example where AI gave him completely incorrect statistics about Naval Academy casualties in WWII, which he solved by simply counting names on a memorial plaque. AI never admits uncertainty or asks for clarification, traits that are essential to developing wisdom. The key distinction is that AI can help you access knowledge, but only humans can transform that knowledge into wisdom through lived experience and practical application.
Embrace Intellectual Humility and Reduce Unnecessary Arguments
True wisdom often manifests as getting into fewer arguments, not because you're always right, but because you recognize what's actually worth your time and energy. (19:43) Holiday references Tom Segura's observation that since becoming a parent, he simply responds "sure, you're right" to most disagreements rather than engaging in pointless debates. This isn't weakness but wisdom - understanding that your time and peace of mind are more valuable than being right about trivial matters. The ability to admit what you don't know and ask better questions becomes more important than defending positions you may not fully understand.
Learning Requires Physical Engagement Beyond Reading
Holiday shares historian David McCullough's example of physically retracing Truman's run to the White House the night FDR died, which revealed insights about Truman's physical fitness that couldn't be gleaned from books alone. (49:30) This principle of "learn, apply, repeat" means you must take knowledge from the theoretical realm into physical experience to truly understand it. Whether it's McCullough running Truman's route or Holiday planning to visit locations for his Stockdale biography, wisdom comes from doing the hard work of experiencing what you're studying rather than just reading about it.
Cultivate Wisdom Through Basic Practices Done Consistently
Holiday identifies several fundamental practices that, when done consistently over time, lead to wisdom: asking questions, reading (especially history and biography), traveling, studying under mentors, and pursuing apprenticeships. (42:25) While these may seem obvious, most people don't actually do them consistently. The key insight is that wisdom isn't a destination you reach but distance you cover - like walking toward the horizon, you'll never arrive, but you can look back and see how far you've traveled. These simple practices, when maintained over a lifetime, compound into significant personal growth and understanding.
Statistics & Facts
- Ryan Holiday's books have sold over 10 million copies in more than 30 languages. (58:08) This statistic demonstrates the widespread appeal and impact of his work on Stoicism and personal development.
- Based on LinkedIn data, 72% of small and medium businesses say using LinkedIn helps them find high quality candidates. This statistic was mentioned during the podcast's sponsor segment about LinkedIn's hiring platform.
- Holiday mentions that 70 classes of Naval Academy graduates served in World War II in some capacity. (12:55) This statistic came up during his discussion about AI's inability to properly calculate historical data, leading him to physically count names on a memorial plaque instead.
