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October 22, 2025 61 mins

What does six years of studying and writing about the Stoic virtues really teach you? In today’s episode, Ryan sits down with longtime research assistant Billy Oppenheimer to look back on how the Stoic Virtues Series came together, from the first hike where the idea was born to the final chapter of Wisdom Takes Work. They talk about what it means to grow up alongside your own work, how each book became the lesson Ryan needed at that moment, and why wisdom can’t be outsourced.


Billy Oppenheimer is Ryan Holiday’s research assistant and the writer behind the newsletter, Six at 6 on Sunday. To read more of his work, check out his website billyoppenheimer.com.


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