Stoa Conversations: Stoicism Applied

Can you say a waterfall is sublime? Or are you just describing your feelings? C.S. Lewis thought this question mattered more than it looks. In the first chapter of The Abolition of Man, he argues that modern education smuggles in a dangerous idea: that value judgments are just reports of emotion. Nothing to debate. Nothing to get right or wrong. Caleb and Michael work through Lewis’s argument in t...

In this episode, Caleb talks with Massimo Pigliucci about his new book, How to Be a Happy Skeptic , and the thinker at its center: Cicero. They trace skepticism from Pyrrho’s radical doubt to the Academics, who found a better path. You don’t need certainty. You need to know how sure to be, then act (or not). The Stoics and skeptics argued for decades over whether truth leaves a mark you can trust....

People love to pair Stoicism and Buddhism. Both blame suffering on desire. Both teach a kind of meditation. Both are about 2,500 years old. So how similar are they, really? Michael and Caleb run a Buddhism 101 for Stoics. They start with the Buddha: a prince who had everything, saw old age, sickness, and death for the first time, and walked away from the palace to figure out why we suffer. From th...

What makes some people excellent at their craft and others just average? Michael walks through a classic 1989 sociology paper on Olympic swimmers and pulls out three lessons that apply directly to Stoic practice. The answer is not what most people expect. It is not extreme effort. It is not raw talent. Excellence turns out to be mundane. It is how you do the boring things, every day, for a long ti...

What’s the core of Stoicism worth keeping? And where does it fall short? Caleb shares his life philosophy in this companion to Michael’s earlier episode. He builds the case for Stoicism from the ground up, then turns it on itself. If happiness has to be up to us, what does that say about the rest of life? And what do you do with the parts of human experience that don’t fit neatly into propositions...

Caleb shares reflections from a recent pilgrimage to Athens. He walks through the ruins of the Stoa Poikile, the painted porch where Stoicism was born, and finds the irony of a philosophy of impermanence enduring in stone fragments thousands of years later. He visits the Acropolis, the Lyceum where Aristotle taught, and thinks about what makes Athens worth visiting today. (00:00) Visiting the Stoa...

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 and it sounds a lot like what the Stoics were after. Caleb and Michael continue their series on Musashi’s Book of Five Rings with the second book: Water . Where Book One laid out general strategy, this one gets into the craft itself: swordsmanship as a l...

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 Stoics actually think about self-examination. Caleb draws a sharp line between the kind of introspection the critics hate — guilt, rumination, dwelling on the past — and the kind Marcus Aurelius practiced: forward-looking, demanding, and grounded i...

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 contemporary of the Stoics and Epicureans, teaching in the same era, competing for the same minds. The results are surprising. Some of Jesus’ core teachings land hard from a Stoic lens. Vice lives in desire, not action. The cowardly adulterer is worse...

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 scratch. The result is something between Stoicism and Aristotle — keeping the Stoic emphasis on character and agency while smuggling in a little more common sense about the human condition. (00:00) Why articulate a personal philosophy? (04:00) The geometri...

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, turning away from others, being ruled by pleasure and pain, and acting without purpose. Sometimes the best path to happiness isn’t chasing it directly, but removing what makes us miserable. (01:00) The Four Items: A Recipe for Happiness (03:50) First: Sto...

The teacher of Epictetus deserves more attention than he gets. Michael returns to Musonius and pulls out three themes: philosophical minimalism, a complicated egalitarianism, and surprisingly specific practical advice. Musonius distrusts overly academic philosophy. He wants simple arguments that appeal to common sense, then action. He argues women should study philosophy because they share the sam...

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’s classic work. The Ground Book lays a foundation that cuts across all pursuits. The conversation draws connections to Stoic ideas about indifference, adaptability, and the danger of becoming too attached to any particular school or method. (03:30)...

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 Stoic Arius Didymus: sound judgment, circumspection, shrewdness, sensibleness, soundness of aim, and ingenuity. Each gets a week. Each gets concrete exercises. This isn’t abstract philosophy. It’s a practical program for sharpening your thinking in...

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 on every Stoic’s reading list, what the New Testament and Stoicism have in common, and the power of keeping philosophical maxims close at hand. The conversation covers a Spanish Jesuit’s handbook on practical wisdom, Plato’s failed attempt to mentor a...

The founders of Stoicism—Zeno, Cleanthes, Chrysippus—all wrote about Homer. Zeno’s longest work was called Homeric Problems . When we read the Odyssey, we’re reading what the Stoics read. We’re studying their curriculum. Following this tradition. Michael and Caleb examine what makes the Odyssey Stoic and what makes it decidedly not. Odysseus perseveres through failures, temptations, and divine opp...

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 recent article: (03:00) The Stoic alignment chart: theory purists to rebels (11:00) Benefits of gatekeeping: maintaining truth and standards (21:00) Epictetus as motivating gatekeeper (26:30) Risks: pedantry and missing the forest for trees (40:00) When gatek...

Some Stoic ideas cut against modern culture. Michael and Caleb examine seven truths that challenge how we think about politics, anger, success, and evil. The Stoics make claims most people won’t like hearing. Politics can’t ruin your happiness. Anger is always wrong. Being a victim doesn’t make you virtuous. You can’t choose all your obligations. Nearly everyone lives in luxury today. Some lives a...

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Caleb explores Seneca’s warning about wealth from Letter 17 and why material success may be a trap. The episode questions whether financial independence really delivers freedom or just creates new forms of dependence. Download the Stoa app (it’s a free download): https://stoameditation.com/pod If you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up wit...

Michael and Caleb examine skeptical modes from Sextus Empiricus. These arguments show why you can’t trust your sense impressions. The Stoics and skeptics were rival schools. But they agreed on one thing: most people live under illusion. The skeptics said you can never overcome that. The Stoics said you can, but only if you’re extremely careful. Both agree you need to interrogate every impression....

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 root problem as oversensitivity to shame. You care too much about violating social norms. The conversation covers when to respect social convention versus when to break it. They examine historical examples of caving gone wrong, from Creon and Medea to m...

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 by a Roman senator facing execution. It’s philosophy tested at the breaking point. The book works through arguments for why you shouldn’t be angry at fortune. Some are practical - don’t complain about losing externals when externals always change. Other...

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. Michael and Caleb explore three Stoic strategies for accepting what you can’t control. (03:20) The Word “Nostalgia” (04:10) Strategy 1: Nothing Belongs to You (12:20) Strategy 2: Expand Your Time Horizon(19:20) Thinking in Life Stages (25:20) Strategy 3...

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 we covered reader questions. Follow us on Substack: https://www.stoaletter.com/ to catch the next one. Get full access to The Stoa Letter at www.stoaletter.com/subscribe