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How The Stoic Virtues Became Ryan’s Greatest Test | Billy Oppenheimer & Ryan Holiday

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Oct 22, 2025

Guest

Billy Oppenheimer

Join Ryan Holiday and his research assistant, Billy Oppenheimer, as they dive deep into the journey of the Stoic Virtues Series. Billy, a talented newsletter writer, shares insights on how the project evolved over six years. They explore the importance of wisdom, the rigorous process behind publishing, and how personal experiences shaped their writing. Discover how Seneca's teachings on knowledge, the role of bibliographies in learning, and the joy of storytelling remain essential to their craft. It's a fascinating look at growth through Stoicism!

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ANECDOTE

Series Born On A Hike

Ryan describes how the Stoic Virtues series began during a hike with his kids and unfolded over six years.
His youngest went from a baby to reading in the time span, illustrating the project's long arc.

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INSIGHT

Books Matched Moment And Need

Each book in the series matched the cultural moment and Ryan's personal life stage.
Wisdom focuses on making sense of our moment, not mere knowledge accumulation.

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ADVICE

Don't Outsource Wisdom

Do not outsource the work of wisdom: there are no shortcuts to becoming wise.
Seneca's example shows you must earn knowledge through effort, not rely on proxies.

Get the Snipd Podcast app to discover more snips from this episode

Why I Want to Talk Less and Listen More

02:56 • 5min

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How the Stoic Virtues Series Began

08:17 • 3min

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Timing, Pace, and Publishing Choices

10:53 • 32sec

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Why Wisdom Had to Be the Final Book

11:25 • 3min

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Seneca's Warning Against Shortcuts

14:00 • 56sec

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Finding Intros and Emergent Ideas

14:56 • 3min

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Cracking the Book's Structure

Montaigne and Unusual Education

23:36 • 2min

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Getting Paid to Learn

25:14 • 4min

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Paying to Leave School and Early Risks

Becoming a Voracious Reader

36:53 • 2min

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Research as a Classroom

39:17 • 4min

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Following Bibliographies to New Ideas

43:01 • 2min

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Verifying Anecdotes and the Izzy Rabbi Story

45:11 • 2min

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Raising Standards for Sources and Claims

47:30 • 7min

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Demystifying Craft Through Apprenticeship

54:31 • 3min

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Discernment, Excellence, and the Creative Snap

57:41 • 1min

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Staying Lit Up by Stories as You Mature

59:05 • 2min

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Choosing Audience Over Technical Complexity

01:00:42 • 58sec

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Material vs Writer's Block

01:01:40 • 3min

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Lincoln's Everlasting Mystery

01:04:42 • 12sec

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Tolstoy on Lincoln's Moral Greatness

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James Patterson

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Don Leslie

Robert Greene

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Wisdom Takes Work

Ryan Holiday

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1984

George Orwell

Published in 1949, '1984' is a cautionary tale by George Orwell that explores the dangers of totalitarianism. The novel is set in a dystopian future where the world is divided into three super-states, with the protagonist Winston Smith living in Oceania, ruled by the mysterious and omnipotent leader Big Brother. Winston works at the Ministry of Truth, where he rewrites historical records to conform to the Party's ever-changing narrative. He begins an illicit love affair with Julia and starts to rebel against the Party, but they are eventually caught and subjected to brutal torture and indoctrination. The novel highlights themes of government surveillance, manipulation of language and history, and the suppression of individual freedom and independent thought.

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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