Most leadership failures don’t come from incompetence.

They come from imbalance.

Too much edge and people comply—but stop trusting you.

Too much kindness and standards quietly collapse.

Real leadership lives in the tension between humanity and consequence.

In this episode, I break down:

• Why edge without warmth creates feaWhy kindness without teeth creates entitlement
• What “teeth” actually mean (and what they don’t)
• The real cost of balanced leadership
• Why every Stoic is a leader—whether you want the role or not

Be kind enough to protect the human.

Be dangerous enough to protect the standard.

In this episode, Brandon sits down with an educator and school principal, Kyle Sarka, to explore Stoic resilience—not as brute toughness, but as endurance guided by wisdom.

The conversation moves fluidly between Stoic philosophy, leadership, fitness, history, and modern life, examining what it really means to persevere when outcomes are uncertain and comfort is abundant.

Rather than glorifying suffering for its own sake, this episode argues that resilience is about knowing when to endure, when to adapt, and when to step back—and having the courage to act either way.

In this episode of The Strong Stoic, I explore a Stoic paradox: the one making the most progress often feels it the least.

Drawing from Epictetus, Marcus Aurelius, and real-world examples from leadership, fitness, and personal responsibility, this episode breaks down why conscientious people feel behind, why growth creates insecurity, and why feeling unstable doesn’t mean you’re weak.

I talk about:

• Why rising standards distort self-perception
• The difference between awareness and anxiety
• Why imposter syndrome often signals expansion
• How to separate your role from unrealistic expectations
• And why shaking knees don’t invalidate strength

If you’ve felt stretched, inadequate, or unsure lately—this episode may help you see that discomfort differently.

Life isn’t fair — and Stoicism never said it would be.

In this episode, we explore what it actually means to live with integrity in a world that doesn’t reward effort, honesty, or discipline in predictable ways. We talk about the difference between character and reputation, when telling the truth is courageous — and when silence is wiser — and how Stoicism helps us respond to unfairness without becoming bitter or defensive.

This is an episode about composure under pressure, clarity in chaos, and learning to carry yourself well even when the outcome isn’t what you hoped for.

If you’ve ever felt unseen, misunderstood, or unfairly judged — this one’s for you.

We all try to live with intention—but life keeps interrupting us.

In this episode, I explore the tension between daily reactivity and long-term vision through a Stoic lens. Why do we keep returning to Marcus Aurelius, Epictetus, and Seneca? Why do we need constant reminders of principles we already know?

Because life pulls us away—daily, hourly, relentlessly.

This episode is about carving out small moments of intention inside a reactive world, and why you don’t need more time—just space—to live with clarity and character.

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

If you enjoy this conversation, please share it with a friend, leave a review, and subscribe for more episodes on Stoicism, character, and the hard work of being a good human.

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