In this episode of The Strong Stoic, I’m joined by classicist and author Inger Kuin to dive deep into the wild, hilarious, and surprisingly practical life of Diogenes—the original Cynic and, in many ways, the “stress test” for Stoic ideas.

We explore:

Who Diogenes was and why his life still matters

• Why he chose to live in a jar, throw away his cup, and embrace radical simplicity
• How his ideas flowed through Crates to Zeno, making him Stoicism’s “intellectual grandfather”
• The difference between training your body vs punishing it
• How temporary discomfort (no-spend months, cabin weekends, etc.) can build real resilience
• Cultural norms, door-holding in Canada, and why Diogenes cared more about justice than etiquette
• Cosmopolitanism and being a “citizen of the cosmos” instead of a slave to one culture’s expectations
• Whether Diogenes was “crazy” or just radically consistent with his philosophy
• The tension between independence and human connection: why Diogenes avoided close attachments—and why Inger (and I) think that might throw the baby out with the bathwater
• How to examine your own motives honestly: are you saying “yes” for good, joy, or just money and status?

We close with practical advice on bringing a bit of Diogenes into modern life without selling your house and moving into a barrel—by questioning your motives, experimenting with less comfort, and rethinking the weight you give to externals.

Guest & Book

Inger’s new book, Diogenes: The Rebellious Life and Revolutionary Philosophy of the Original Cynic, is out November 11, 2025 and available wherever you buy books (hardcover, e-book, and audiobook).

🔗 Learn more about Inger and her work: ingerkuin.com

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Show Notes / Key Timestamps

• 00:00 – Introduction & timeboxing the conversation
• 01:10 – Who was Diogenes? Exile from Sinope, life in Athens, and his role as Stoicism’s “grandfather” through Crates and Zeno.
• 05:35 – Diogenes as a stress test for Stoic principles
• 06:40 – Radical simplicity: living in a jar and throwing away the cup
• 10:40 – Temporary discomfort vs permanent renunciation
• 13:25 – Door-holding in Canada and the problem with overvaluing etiquette
• 18:20 – Cosmopolitanism: being a citizen of the cosmos
• 22:35 – “The dog” and “a raving Socrates”: was Diogenes mad?
• 28:20 – Shame, shamelessness, and why the world doesn’t end when you break a norm
• 29:50 – Needing to be liked vs needing to be understood
• 32:30 – Did Diogenes go too far in rejecting close relationships?
• 36:50 – Externals vs internals: Epictetus, wealth, and Diogenes’ influence
• 40:40 – How Inger uses Diogenes’ lens to make real-life decisions
• 43:00 – Watching your intentions: status, money, or genuine good?
• 43:50 – Book details and live events
• 46:30 – Closing reflections & mutual appreciation