Imposter syndrome doesn’t mean you’re weak.

It often means you’re growing.

In this episode of The Strong Stoic Podcast, I explore imposter syndrome through a Stoic lens—why it shows up during periods of growth, why it often steals our sleep, and why it may actually be evidence that your character is strengthening.

When we take on new roles—at work, in relationships, as parents, or in life—we carry weight we haven’t carried before. Our knees shake. Our confidence wavers. And at night, when there’s no more room in the day to process it all, the mind takes over.

Drawing on Stoic philosophy, personal experience, and thinkers like Marcus Aurelius, Epictetus, and Viktor Frankl, this episode reframes restless nights not as failure—but as adaptation.

Life doesn’t necessarily get easier.

We get stronger.

But there’s also a limit. Not all weight can be squatted. Growth requires ambition and humility—knowing when to stretch your capacity, and when the load risks crushing you.

This episode is for anyone:

Taking on a new responsibility

• Feeling behind, unqualified, or overwhelmed
• Losing sleep during a season of growth
• Wondering whether they’re built for the weight they’re carrying

You are.

But strength is built under load—and with rest.

In this episode, Brandon explores Hemingway’s famous line: “The world breaks everyone.”

But instead of treating breaking as failure, we look at it through the Stoic lens—as a natural part of being human, and the raw material for growth.

From tendon micro-tears in heavy lifting, to emotional micro-fractures in leadership and relationships, we break far more often than we admit. And yet every fracture offers us a choice: shatter through denial… or rebuild into something stronger.

Brandon talks about:

• Why strong people break harder

• The illusion of invulnerability

• Micro-damage as a metaphor for character development

• Stoic recovery: reflection, realignment, rebuilding

• How to turn every break into wisdom

• Why breaking means you’re becoming—not failing

If you’re carrying a heavy load, if you feel cracks forming, or if you’ve recently broken and are trying to make sense of it—this episode will help you rebuild strong at the broken places.

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