Why Negative Examples Teach Wisdom

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New York Times bestselling author Ryan Holiday returns to From the Green Notebook for his third conversation with Joe—this time diving into the themes of his latest and final book in the Stoic Virtues series, Wisdom Takes Work. 

In this wide-ranging conversation, Ryan and Joe discuss the importance of curiosity, humility, and deep reflection in a world where shortcuts and surface-level thinking often dominate. They explore how writing, reading, and journaling serve as tools for developing wisdom—and how, for both leaders and creators, clarity of thought begins with clarity on paper.

Listeners will gain insights into Ryan’s approach to writing books, the power of writing as intellectual accountability, and what he’s learned from studying figures like Montaigne, Lincoln, and even Elon Musk. Along the way, Ryan opens up about his own evolution as a writer, the dangers of intellectual arrogance, and why the pursuit of wisdom is a lifelong endeavor.

In this episode, Joe and Ryan explore:

• Why wisdom isn’t something you have but something you earn through continuous effort
• How writing forces clarity, accountability, and humility in thinking
• The danger of “bad bricks” in our belief systems—and how to guard against misinformation
• Why note-taking and reflection are a form of “time travel” that benefit your future self
• How curiosity and skepticism help protect us from manipulation in an AI-driven world
• The difference between intelligence and wisdom—and why power without self-awareness can be destructive
• Why Ben Franklin remains a model of intellectual and social intelligence

Whether you’re leading a team, writing your next book, or simply trying to think more clearly, this episode offers a masterclass in slowing down, asking better questions, and doing the hard work of becoming wiser.

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