Wisdom Takes Work with Ryan Holiday

15 snips

Oct 18, 2025

Ryan Holiday, a New York Times bestselling author and Stoic philosophy enthusiast, discusses themes from his latest book, Wisdom Takes Work. He explores how humility and curiosity develop wisdom in an age of surface-level thinking. Holiday emphasizes writing as a tool for clarity and accountability, revealing gaps in understanding. He contrasts intelligence with wisdom, using figures like Montaigne, Lincoln, and Elon Musk to illustrate both successes and failures of wisdom, while stressing the importance of continuous learning and critical thinking.

Ask episode

AI Snips

Chapters

Books

Transcript

Episode notes

INSIGHT

Wisdom Is Earned Not Defined

Ryan Holiday says wisdom cannot be fully defined and is a compound quality of experience, intuition, and learning.
He defines wisdom as something earned through sustained hard work and methodical practice.

ANECDOTE

Three Characters Framing Wisdom

Ryan frames Montaigne and Lincoln as bookends of wisdom and uses Elon Musk as a middle cautionary figure.
He traces Musk's rise from self-education to later public mistakes as a warning about intelligence without tempering forces.

ADVICE

Use Writing To Force Clarity

Do write to clarify and hold yourself intellectually accountable; writing forces you to structure and refine thoughts.
Use editing and audience perspective to tighten arguments and preempt objections.

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

Get the app

Send us a text

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.

A Special Thanks to Our Sponsors!

Veteran-founded Adyton. Step into the next generation of equipment management with Log-E by Adyton. Whether you are doing monthly inventories or preparing for deployment, Log-E is your pocket property book, giving real-time visibility into equipment status and mission readiness. Learn more about how Log-E can revolutionize your property tracking process here!

Meet ROGER Bank—a modern, digital bank built for military members, by military members. With early payday, no fees, high-yield accounts, and real support, it’s banking that gets you. Funds are FDIC insured through Citizens Bank of Edmond, so you can bank with confidence and peace of mind.