Stoa Conversations: Stoicism Applied

Musashi’s Book of Five Rings: The Water Book (Episode 224)

07 Apr 2026

Contributed by Lukas

Your mind should be quietly vibrating. Not tense, not slack, not leaning in any direction. That’s Musashi’s opening instruction in the Water Book ...

The Stoic Case for Introspection (Episode 223)

24 Mar 2026

Contributed by Lukas

Some guy goes on a podcast and argues against introspection. Caleb pushes back.This solo episode uses the viral debate as a launching pad for what the...

What Stoics Find in the New Testament (Episode 222)

10 Mar 2026

Contributed by Lukas

Michael picks up the New Testament for the first time and does something unusual: he treats Jesus not as a religious figure, but as a philosopher. A c...

Michael's Life Philosophy

24 Feb 2026

Contributed by Lukas

What does a historian of Stoicism actually believe? Michael puts his money where his mouth is and lays out his personal philosophy of life from scratc...

Four Ways To Be Happy (Episode 220)

27 Jan 2026

Contributed by Lukas

Marcus Aurelius gives us a recipe for happiness in Meditations 2.16.Caleb breaks down the four ways we do the exact opposite: fighting reality, turnin...

The Roman Socrates Tells Us How To Live (Episode 219)

20 Jan 2026

Contributed by Lukas

The teacher of Epictetus deserves more attention than he gets. Michael returns to Musonius and pulls out three themes: philosophical minimalism, a com...

Musashi’s Book of Five Rings: The Ground Book (Episode 218)

13 Jan 2026

Contributed by Lukas

What can a 17th-century samurai who won 60 duels to the death teach us about living well?Caleb and Michael explore the first book of Miyamoto Musashi’...

How to Be Smarter (Episode 217)

06 Jan 2026

Contributed by Lukas

What do the Stoics mean by intelligence? And how do you actually develop it?Caleb breaks down prudence into six trainable components from the ancient ...

What We Read, Watched, and Learned in 2025 (Episode 216)

30 Dec 2025

Contributed by Lukas

Michael and Caleb look back on their favorite reads, conversations, and discoveries from the year.They discuss why Cicero’s On Ends deserves a spot ...

A Stoic Book Review of the Odyssey (Episode 215)

23 Dec 2025

Contributed by Lukas

The founders of Stoicism—Zeno, Cleanthes, Chrysippus—all wrote about Homer. Zeno’s longest work was called Homeric Problems. When we read the Od...

Who Gets To Call Themselves Stoic (Episode 214)

16 Dec 2025

Contributed by Lukas

Who gets to call themselves a Stoic? Michael and Caleb tackle the issue of who is and isn’t a Stoic. Grounding their discussion in Michael’s recen...

Stoic Ideas That Cut Against Modern Culture (Episode 213)

09 Dec 2025

Contributed by Lukas

Some Stoic ideas cut against modern culture. Michael and Caleb examine seven truths that challenge how we think about politics, anger, success, and ev...

Conversation w/ Daniel Greco - Yale Professor of Philosophy

02 Dec 2025

Contributed by Lukas

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Becoming Rich Won't Make You Free (Episode 212)

02 Dec 2025

Contributed by Lukas

Caleb explores Seneca’s warning about wealth from Letter 17 and why material success may be a trap. The episode questions whether financial independ...

Question Every Impression | Ancient Skepticism (Episode 211)

25 Nov 2025

Contributed by Lukas

Michael and Caleb examine skeptical modes from Sextus Empiricus. These arguments show why you can’t trust your sense impressions. The Stoics and ske...

How to Resist Pressure (Episode 210)

18 Nov 2025

Contributed by Lukas

Ever say yes when you meant no? Caleb and Michael explore Plutarch’s guide to resisting pressure and not being a pushover.Plutarch identifies the ro...

How to Face Hardship | Boethius and The Consolation of Philosophy (Episode 209)

11 Nov 2025

Contributed by Lukas

When you’re in prison waiting to die, what can philosophy do for you? Michael and Caleb read Boethius’s Consolation of Philosophy - a book written...

Dealing with Change (Episode 208)

04 Nov 2025

Contributed by Lukas

Nothing stays the way you want it. Your job disappears. Relationships end. Everyone you know will die. The cities you live in will cease to exist. Mic...

Ask Us Anything (Episode 207)

28 Oct 2025

Contributed by Lukas

Thank you for tuning into our live video! Join us for our next live video in the app.This episode is taken from our recent Substack Live episode where...

Eclecticism with Anya Leonard from Classical Wisdom (Episode 206)

21 Oct 2025

Contributed by Lukas

How much ancient philosophy should you steal? Caleb and Anya Leonard from Classical Wisdom explore the art of philosophical eclecticism, from Heraclit...

Hunters Talk About Spears (Episode 205)

14 Oct 2025

Contributed by Lukas

Philosophy talks about big ideas. The good life. Virtue. Happiness. But talking about aspirations isn’t enough. You need mechanisms—concrete pract...

Stoicism, Freedom, and Ernst Jünger with Sam Alaimo (Episode 204)

07 Oct 2025

Contributed by Lukas

Sam Alaimo is a Navy SEAL who discovered Stoicism after leaving the military. He is a cofounder of Zero Eyes, an AI company stopping gun violence, and...

Ancient and Modern Myths with Michael Fontaine (Episode 203)

30 Sep 2025

Contributed by Lukas

Have we traded ancient wisdom for modern myths?In this episode, Caleb speaks with Cornell classics professor Michael Fontaine.Fontaine argues that psy...

Anger And Society (Episode 202)

23 Sep 2025

Contributed by Lukas

Caleb explores why anger works as social currency. If you're not angry when someone hurts your friend, do you really care about them?People aren't wro...

Stoicism & Anger w/ Donald Robertson

18 Sep 2025

Contributed by Lukas

Caleb and Michael interview Donald J. Robertson on Anger and Stoicism.We’ll be doing more live events and chats. Get the Substack app and stay tuned...

Two Practices For Zen Stoicism (Episode 201)

16 Sep 2025

Contributed by Lukas

Most of our thoughts are wrong. That's the problem with thinking—we make judgments about good and bad that don't match reality. Zen practitioners fi...

Should Stoics Use AI (Episode 200)

09 Sep 2025

Contributed by Lukas

Should Stoics use AI? Michael and Caleb tackle this modern question by examining how ancient philosophy guides our relationship with new technology. T...

Stoic Exercise Tier List (Episode 199)

02 Sep 2025

Contributed by Lukas

Caleb and Michael going live with Donald J. Robertson this Thursday at 5 PM ET. Join us on the Substack app!https://open.substack.com/live-stream/5379...

Effective Altruism as a Life Philosophy (Episode 198)

26 Aug 2025

Contributed by Lukas

Can you do good and do it wrong? Michael and Caleb examine effective altruism - the movement that treats helping others like an optimization problem.T...

Memory Palaces and Stoic Eating with Andrew Perlot (Episode 197)

19 Aug 2025

Contributed by Lukas

How memory and diet shape your character. Andrew Perlot , former journalist and health coach, explains why the Stoics obsessed over both.(00:00:56) Wh...

The Unfettered Mind | Stoic Zen (Episode 196)

12 Aug 2025

Contributed by Lukas

Caleb and Michael explore Takuan Soho's The Unfettered Mind, examining how Zen Buddhism approaches mental training through the concept of "no mind." T...

The Life of Plato (Episode 195)

05 Aug 2025

Contributed by Lukas

Philosophy meets biography in this deep dive into Robin Waterfield's new book on Plato. Michael and Caleb explore how the philosopher's life shaped hi...

10 Key Stoic Ideas (Episode 194)

29 Jul 2025

Contributed by Lukas

Michael breaks down the ten most important concepts you need to understand ancient philosophy's most practical school of thought.These are the core id...

When Being Good at Your Job Makes You a Bad Person (Episode 193)

22 Jul 2025

Contributed by Lukas

What happens when the roles life gives you conflict with being a good person? Caleb and Michael tackle one of Stoicism's puzzles: when excellent perfo...

The Ring of Gyges (Episode 192)

15 Jul 2025

Contributed by Lukas

What would you do if you could get away with anything?Plato's famous thought experiment cuts straight to the heart of human nature. If you had a ring ...

Therapy vs Philosophy (Episode 191)

08 Jul 2025

Contributed by Lukas

When life hits hard, where do you turn? Philosophy, therapy, or coaching? Michael and Caleb examine and debate the fundamental differences between the...

Seneca On The Creation of Earthquakes (Episode 190)

01 Jul 2025

Contributed by Lukas

In this episode, Caleb and Michael review the 2023 film "Seneca, On the Creation of Earthquakes" starring John Malkovich. They explore how the movie p...

Marcus Aurelius On What To Read (Episode 189)

24 Jun 2025

Contributed by Lukas

Should you really be reading all those "great books"? Marcus Aurelius had strong opinions about this. He repeatedly told himself to throw away his boo...

The Stoic Paradoxes (Episode 188)

17 Jun 2025

Contributed by Lukas

The Stoics made claims that sounded completely crazy to regular people. Only virtue is good. All crimes are equally bad. Everyone who isn't perfectly ...

Misunderstanding the Dichotomy of Control (Episode 187)

10 Jun 2025

Contributed by Lukas

Most people learn about Stoicism through the dichotomy of control. It sounds simple: focus on what's up to you, ignore what isn't. But this apparent s...

An Underrated Stoic Exercise: Circumscribing The Present (Episode 186)

03 Jun 2025

Contributed by Lukas

Are you stressed about the future? Deep-dive into this Stoic exercise from Marcus Aurelius for living the moment, without anxiety or regret.Michael Tr...

The Laughing Cynic Who Taught Stoicism's Founder (Episode 185)

27 May 2025

Contributed by Lukas

Discover the philosopher who transformed Zeno from shipwrecked merchant to Stoicism's founder. While modern cynics see only self-interest, Crates live...

Introduction to Aristotle's Golden Mean (Episode 184)

20 May 2025

Contributed by Lukas

In this episode, Michael Tremblay and Caleb Ontiveros explore Aristotle's ethics, focusing on his doctrine of virtue as the golden mean. They break d...

Wrestling with Stoic Ethics: Cicero's On Ends V (Episode 183)

13 May 2025

Contributed by Lukas

In this final exploration of Cicero's "On Ends," Michael and Caleb break down Book V, where Cicero reveals his own philosophical sweet spot – an Ari...

The Stoic Fragments: Hidden Wisdom from Epictetus (Episode 182)

06 May 2025

Contributed by Lukas

Discover the hidden gems of Stoic philosophy in this exploration of Epictetus' fragments - those powerful passages preserved by other philosophers but...

Forgive Your Enemies with Epictetus (Episode 181)

29 Apr 2025

Contributed by Lukas

In this episode, Michael Tremblay explores Epictetus' radical approach to anger and forgiveness. Discover why the Stoics believed we should pity rathe...

Trolleys, Torture, and Moral Dilemma's (Episode 180)

22 Apr 2025

Contributed by Lukas

Michael and Caleb dive into classic philosophical thought experiments to uncover Stoic solutions to impossible choices. From the infamous Trolley Prob...

Why Stoicism is False | Cicero's On Ends IV (Episode 179)

15 Apr 2025

Contributed by Lukas

Caleb and Michael break down Book IV of Cicero's "On Ends" - his powerful critique of Stoic ethics.Discover why Cicero believed the Stoics fell short ...

7 Stoic Habits You Can Start Today (Episode 178)

08 Apr 2025

Contributed by Lukas

Living like a Stoic is about getting the little things right.  In this episode, Michael Tremblay discusses 7 Stoic habits you can start today to buil...

The Classic Defense Of Stoic Ethics | On Ends Book III (Episode 177)

01 Apr 2025

Contributed by Lukas

In this episode of Stoic Conversations, Caleb and Michael break down Book III of Cicero's On Ends - the definitive ancient defense of Stoic ethics.Dis...

Seneca's Medea | Revenge, Violence, and Stoicism (Episode 176)

25 Mar 2025

Contributed by Lukas

Seneca's brutal play "Medea" reveals what happens when rage takes control. A betrayed wife, an indecisive husband, and a tragic ending that challenges...

Against The Epicureans | On Ends Book II (Episode 175)

17 Mar 2025

Contributed by Lukas

Caleb and Michael take on Book II of Cicero’s On Ends.  In this books Cicero goes off against the Epicureans.  What do you think?On Ends Book IAri...

Politics And Amor Fati With Erick Cloward (Episode 174)

11 Mar 2025

Contributed by Lukas

In this episode, Michael talks with Erick Cloward, the host of the Stoic Coffee Break Podcast.   Erick talks about his journey into Stoicism, his re...

Making Proper use of Impressions with Epictetus (Episode 173)

04 Mar 2025

Contributed by Lukas

Epictetus tells us the chief task of philosophy is just one thing: Make proper use of impressions.  In this episode, Michael Tremblay does a deep div...

The Epicureans | On Ends Book I (Episode 172)

25 Feb 2025

Contributed by Lukas

In 45 BC, amid the turmoil of the Roman Civil War, Cicero wrote one of philosophy's most important works on the meaning of life. This episode unpacks ...

The First Cynic | Antisthenes (Episode 171)

18 Feb 2025

Contributed by Lukas

Caleb and Michael discuess teacher of Diogenes and the grandfather of Stoicism. Before there were Stoics arguing about virtue, there was Antisthenes. ...

Stoic Guide to Mastering Desire | Epictetus Handbook 14 (Episode 170)

11 Feb 2025

Contributed by Lukas

Freedom isn't about having enough money to do what you want. It's about wanting what you can actually control. In this episode, Michael breaks down Ep...

Going Meta With Metacognition (Episode 169)

04 Feb 2025

Contributed by Lukas

The ancient Stoics never used the term "metacognition," but this modern psychological concept illuminates the core of their philosophy. Michael and Ca...

Top 7 Things I Learned about Stoicism from Running (Episode 168)

28 Jan 2025

Contributed by Lukas

Ancient and modern Stoics aren't just thinkers - they are runners too. In this episode, Caleb explores how the simple act of running illuminates core ...

Aristippus: The Philosopher Who Mastered Pleasure (Episode 167)

21 Jan 2025

Contributed by Lukas

Meet ancient Greece's original hedonist. Unlike later philosophers who preached asceticism, Aristippus embraced luxury, courted kings, and still kept ...

The Roman Emperor on Strength, How to Transform Misfortune Into Fortune, And Death (Episode 166)

14 Jan 2025

Contributed by Lukas

In this episode, Michael and Caleb explore Meditations 4.49-51, where Marcus Aurelius discusess resilience, misfortune, death, and simplicity. Be like...

Goodhart's Law and Stoicism (Episode 165)

07 Jan 2025

Contributed by Lukas

Goodhart’s Law says: when a measure becomes a target, it ceases to be a good measure.  But if that’s true, how should we measure our philosophica...

Stoicism for When You're Stuck (Episode 164)

31 Dec 2024

Contributed by Lukas

Get these tested Stoic strategies pull you out of bed and back into life's beauty. Michael and Caleb explore ancient wisdom for reconnecting with mean...

Why Other People Do Wrong – Socrates Was Right! (Episode 163)

24 Dec 2024

Contributed by Lukas

No one chooses to be wrong. This core Stoic teaching, inherited from Socrates, shaped how ancient philosophers viewed human behavior and mistakes. In ...

The Second Arrow (Episode 162)

17 Dec 2024

Contributed by Lukas

Pain is inevitable. Suffering is optional. In this episode, we explore a powerful Buddhist concept that mirrors Stoic wisdom: the Second Arrow. The fi...

Noah Rasheta on Stoicism vs. Buddhism (Episode 161)

10 Dec 2024

Contributed by Lukas

Author and Podcaster Noah Rasheta explores the parallels between Buddhism and Stoicism with Michael Tremblay.Whether you're seeking practical wisdom o...

Making Epistemology Cool Again (Episode 160)

03 Dec 2024

Contributed by Lukas

Caleb and Michael discuss Stoic epistemology—how to think well, avoid ignorance, and form justified beliefs. They explore the importance of skeptici...

The Intuitive Case for Stoicism (Episode 159)

26 Nov 2024

Contributed by Lukas

Caleb Ontiveros makes the case that Stoicism is more intuitive than you might think. He argues that if minor setbacks don't ruin our lives, why should...

Bryan Caplan on Epicureanism, Agency, and Self-Help (Episode 158)

19 Nov 2024

Contributed by Lukas

Bryan Caplan, economist and bestselling author, discusses practical wisdom from modern economics and ancient philosophy.He argues against medicalizati...

You Are Not Your Thoughts But You Are How You Think (Episode 157)

12 Nov 2024

Contributed by Lukas

Michael and Caleb explore how understanding ourselves as our faculty of choice—not our bodies, possessions, or reputation—transforms our approach ...

The Stoic's Guide to Perspective: Epictetus's Handbook 26 (Episode 156)

05 Nov 2024

Contributed by Lukas

Why Epictetus tells us to compare our suffering to others.  This simple exercise can help you in times of crisis.  Join Michael as he breaks down Ep...

Spencer Klavan on Science vs. Religion (and Why the Stoics Were Not Materialists) (Episode 155)

29 Oct 2024

Contributed by Lukas

Has Science proven that the world is nothing more than a physical machine without overarching purpose?Spencer Klavan’s most recent book answers with...

Why Most Things Do Not Matter: Indifferents (Episode 154)

22 Oct 2024

Contributed by Lukas

What if the things you obsess over daily don't ultimately matter? The ancient Stoics had a radical idea: most of what we chase - wealth, fame, even he...

Epictetus on Insults, Fortitude, and Doing Your Best (Episode 153)

15 Oct 2024

Contributed by Lukas

In this episode, Michael and Caleb break down Handbook 42, where Epictetus lays out Socratic Intellectualism and explains why people's harsh words say...

The Stoic Wealth Mindset (Episode 152)

08 Oct 2024

Contributed by Lukas

Money talks, but what do the Stoics say about it?In this episode, Caleb and Michael dive into the relationship between Stoicism and wealth. They explo...

Brigid Delaney on Reasons not to Worry (Episode 151)

01 Oct 2024

Contributed by Lukas

Michael talks with Brigid Delaney about her journey into Stoicism, the value it has had in her life, and the unique role it has to play in helping oth...

Stoic Justice (Episode 150)

24 Sep 2024

Contributed by Lukas

The four pillars of Stoic Justice.Justice isn't just about courtrooms and laws. For the Stoics, it was a way of life. In this episode, Caleb and Micha...

Seneca's Advice On Nervous Ticks, Embarrassment, and Cringe (Episode 149)

17 Sep 2024

Contributed by Lukas

Blushing, sweating, stumbling over words - we've all been there. But what if these physical reactions are holding you back from greatness? In this epi...

Stoic Risk Tolerance (Episode 148)

10 Sep 2024

Contributed by Lukas

In this episode, Caleb and Michael explore how Stoicism reframes our understanding of risk, teaching us to embrace uncertainty while focusing on what ...

Toxic Positivity And Stoicism (Episode 147)

03 Sep 2024

Contributed by Lukas

Is Stoicism just toxic positivity? No, obviously.But what's the difference between toxic positivity and unrealistic optimism?  And how can Stoics avo...

Seneca On Solitude (Episode 146)

27 Aug 2024

Contributed by Lukas

The Stoic art of solitude and self-consistencyCan you be alone with your thoughts? Seneca's Letter X challenges us to master the art of solitude.In th...

Applying Stoicism To First JiuJitsu Competition (Episode 145)

20 Aug 2024

Contributed by Lukas

Join Caleb and Michael as they dissect the mental game of competition and explore how ancient philosophy can give us an edge in modern battles – bot...

Diogenes The Cynic, Freedom, And Living In A Barrel (Episode 144)

13 Aug 2024

Contributed by Lukas

Diogenes: the man who lived in a barrel and inspired Stoic philosophy.In this episode, Michael and Caleb explore the life and ideas of Diogenes the Cy...

Johnathan Bi on Nietzsche and the Validity of the Ad Hominem (Episode 143)

06 Aug 2024

Contributed by Lukas

Caleb Ontiveros speaks with Johnathan Bi, an entrepreneur and philosopher, about Friedrich Nietzsche's critique of Stoicism and egalitarianism.The con...

What Many People Misunderstand About The Dichotomy Of Control (Episode 142)

30 Jul 2024

Contributed by Lukas

In this episode of Stoic Conversations, Michael Tremblay offers a deep dive into one of Stoicism's most popular concepts: the Dichotomy of Control. Dr...

Darius Foroux On The Stoic Path To Wealth (Episode 141)

23 Jul 2024

Contributed by Lukas

Should Stoics become rich? What is your relationship to money? Caleb speaks with Darius Foroux about his new book The Stoic Path To Wealth. They discu...

Stoic Practical Wisdom and Prudence (Episode 140)

16 Jul 2024

Contributed by Lukas

The ancient Stoic, Arius Didymus, provided a framework for practical wisdom and prudence. It’s still applicable today.CourageModeration(02:29) Readi...

Modern Self Help: The Good, The Bad (Episode 139)

09 Jul 2024

Contributed by Lukas

Michael and Caleb discuss the differences between modern self help and Stoicism – where self help is useful, where it isn’t, and recommend their f...

Reading the Roman Emperor: Meditations 2.6-10 (Episode 138)

02 Jul 2024

Contributed by Lukas

Caleb and Michael read through Marcus Aurelius’s Meditations. Specifically: Meditations 2.6-2.10.There are several essential themes in these passage...

Why Stoicism Is True (Episode 137)

25 Jun 2024

Contributed by Lukas

This one is different.Caleb reads from his essay, Why Stoicism Is True. It’s a short encapsulation of the what he takes to be the three most importa...

Essential Stoic Concepts: Indifferents (Episode 136)

18 Jun 2024

Contributed by Lukas

In this episode, Michael presents the Stoic idea of "indifferents." It’s one of the key ideas behind Stoicism, one’s that often misunderstood but ...

Stoic Moderation (Episode 135)

11 Jun 2024

Contributed by Lukas

“Moderation is subdivided into good discipline, seemliness, modesty, and self-control.”The ancient Stoic breakdown of moderation is essential for ...

Stoic Attention (Episode 134)

04 Jun 2024

Contributed by Lukas

In this conversation, Michael and Caleb discuss Epictetus’s chapter On Attention (Discourses 4.12). It’s an essential reading from the Stoic maste...

Stoic Courage (Episode 133)

28 May 2024

Contributed by Lukas

The Stoics promoted the four cardinal virtues: courage, moderation, justice, and wisdom. In this episode, we talk about Stoic courage. Caleb and Micha...

Parker Settecase on Journaling Like Marcus Aurelius (Episode 132)

21 May 2024

Contributed by Lukas

Do you want to learn how to Journal like Marcus Aurelius?Parker Settecase explains different approaches to journaling, writing, and recording your tho...

Lessons From Epicureanism (Episode 131)

14 May 2024

Contributed by Lukas

"The thought for today is one which I discovered in Epicurus; for I am wont to cross over even into the enemy's camp, – not as a deserter, but as a ...

Judith Stove on Virtue, Providence, and Marcus as God (Episode 130)

07 May 2024

Contributed by Lukas

Why did talking about virtue fall out of fashion – and why is it coming back now?In this conversation, Caleb speaks with Judith Stove about that ver...

What Did The Stoics Believe About God? (Episode 129)

30 Apr 2024

Contributed by Lukas

The ancients talked about Nature, Reason, Zeus, and God – but what did they mean by it?In this conversation, Michael tells us who or what the Stoic ...

Alex Petkas on Pompey and Posidonius (Episode 128)

23 Apr 2024

Contributed by Lukas

The philosopher and the general. Stoic philosophy in ancient Roman history.In this podcast, Caleb speaks with Alex Petkas about Pompey and Posidonius ...

Ambition (Episode 127)

16 Apr 2024

Contributed by Lukas

“Show me a man who is not a slave; one is a slave to lust, another to greed, another to ambition.”– Seneca In this conversation, Michael and Cal...