Stoa Conversations: Stoicism Applied

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 in a clear standard of how to live.(00:00) The VC’s argument against introspection(03:00) Marcus Aurelius as counterexample(05:00) What Stoic introspection is(08:30) Self-criticism: proleptic, not punishing(13:30) Knowing yourself: the Delphic tradition(18:00) Why Stoic introspection isn’t rumination(20:30) The risks: diminishing returns and the hall of mirrors(23:30) How much introspection is enoughDownload the Stoa app (it’s a free download): https://stoameditation.com/podIf you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/Thanks to Michael Levy for graciously letting us use his music in the conversations:https://ancientlyre.com/ Get full access to The Stoa Letter at www.stoaletter.com/subscribe

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 than the bold one — he has two vices instead of one. Virtue demands the right reason, not just the right deed. Film your charity for Instagram and you’ve already collected your reward. Turn the other cheek isn’t passive — it’s radical character consistency. And loving your enemies? If you only love your friends, you’re not doing anything impressive. Everyone does that.But then things get complicated. What’s the ethical function of miracles? Why does faith matter if the Stoics demand knowledge? And if heaven promises a hundredfold return on your sacrifice, doesn’t Christianity collapse into delayed hedonism?Michael and Caleb wrestle with all of it — the overlaps, the tensions, and the parts that don’t resolve neatly.(03:00) Reading Jesus as a Philosopher(07:30) Vice Lives in Desire, Not Action(12:30) Virtue Requires the Right Reason(17:00) Turn the Other Cheek(22:00) Love Your Enemies(28:00) Cast the First Stone(37:30) The Danger of Appearances(41:30) Where a Stoic Pushes Back(51:20) Ted Chang and the Literature of FaithDownload the Stoa app (it’s a free download): https://stoameditation.com/podIf you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/Thanks to Michael Levy for graciously letting us use his music in the conversations:https://ancientlyre.com/ Get full access to The Stoa Letter at www.stoaletter.com/subscribe

A historian lays out a personal life philosophy mixing Stoic character with Aristotelian common sense. They explain a geometric, axiomatic method and a eudaimonistic framework that ranks goods and accepts degrees of happiness. The conversation covers human nature, unequal agency, genuine hardship, and a capabilities-based obligation to help others flourish.

A short tour of Marcus Aurelius' four obstacles to happiness and how avoiding them can free you. Conversations cover surrendering to reality, cultivating healthy relationships, resisting being driven by pleasure or pain, and living with clear purpose. A closing reading from Meditations ties the ideas together.

Delve into the practical wisdom of Musonius Rufus, a lesser-known Roman Stoic. Discover his take on philosophical minimalism: he prioritizes simple, strong arguments paired with actionable steps. Musonius advocates for the philosophical education of women while acknowledging distinct social roles. He controversially praises physical labor as ideal for philosophers and offers unique lifestyle advice, from raw diets to growing out your hair. His blend of conservative and progressive views sparks intriguing dialogue on ethics and daily living.

Explore the profound lessons from Miyamoto Musashi, a 17th-century samurai, who shares insights on living well through his classic work. Delve into the importance of mastering a craft as a path to philosophical understanding. Discover the four ways of life—warrior, carpenter, farmer, and merchant—and how adaptability trumps attachment to any one style. Learn about the ethical dimension of living with honesty and the significance of rhythm and timing in both combat and everyday life. Musashi's nine rules provide a practical framework for personal growth.

Explore the Stoic definition of intelligence and its practical applications. Delve into six components of prudence, including sound judgment, circumspection, and shrewdness. Learn how to cultivate these skills with concrete exercises each week. Discover techniques for improving decision-making, maintaining current perceptions, and honing quick reactions. Engage in deeper evaluations and set clear targets to sharpen your thinking. Each facet leads you to a more ingenious approach to problem-solving in daily life.

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 tyrant, and which Stoic exercises actually work in daily life. Finally, they wrap up with moves of the year.(01:00) Cicero’s On Ends: Why It’s the Perfect Second Book(08:10) Reading the New Testament as a Stoic(17:00) The Art of Worldly Wisdom by Baltasar Gracián(24:20) The Life of Plato: Philosophy Meets Tyranny(28:00) Stoic Maxims as Mental Magic(32:20) The 10 Stoic Exercises: What Actually Works(37:20) Movie Picks: Lord of the Rings and The Great BeautyDownload the Stoa app (it’s a free download): https://stoameditation.com/podIf you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/Thanks to Michael Levy for graciously letting us use his music in the conversations:https://ancientlyre.com/ Get full access to The Stoa Letter at www.stoaletter.com/subscribe

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 opposition for twenty years. He just wants to go home. That single-minded endurance is deeply Stoic.But Homer’s hero also cries openly, grieves for years, and slaughters everyone who wronged him. He’s a brilliant bullshitter who tells elaborate lies even to gods. Is that Stoic?The tension between these traditions reveals something important about both.(0:00) Why the Stoics Studied Homer(6:30) Sparknotes(14:30) Stoic Theme: Perseverance Through Failure(22:40) Stoic Theme: Intelligence as Virtue(26:00) Stoic Theme: Cosmopolitanism and Being a Good Guest(35:00) Stoic Theme: Tact as Social Virtue(42:10) Non-Stoic Theme: The Emotional Hero(46:30) Non-Stoic Theme: Revenge and the Suitors(54:00) Non-Stoic Theme: The TricksterDownload the Stoa app (it’s a free download): https://stoameditation.com/podIf you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/Thanks to Michael Levy for graciously letting us use his music in the conversations: https://ancientlyre.com/ Get full access to The Stoa Letter at www.stoaletter.com/subscribe

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 gatekeeping becomes antisocial(46:30) Finding the balanceDownload the Stoa app (it’s a free download): https://stoameditation.com/podIf you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/Thanks to Michael Levy for graciously letting us use his music in the conversations:https://ancientlyre.com/ Get full access to The Stoa Letter at www.stoaletter.com/subscribe