Stoa Conversations: Stoicism Applied

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

Explore how Stoic philosophy challenges modern beliefs with seven provocative truths. Happiness isn't determined by politics, and anger is deemed ineffective and harmful. Victimhood and success don't grant moral authority, and our roles in life come with obligations we can't choose. Discover that most people live in luxury today, and some lives are inherently better for flourishing. Plus, delve into the idea that no one truly intends to do evil, highlighting the importance of understanding over judgment.

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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/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 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.(3:20) Skeptics vs Stoics on impressions (9:00) Different animals see differently (15:30) Humans disagree with each other (20:20) Your senses contradict themselves (26:40) Your disposition changes everything (31:50) The ideal disposition for truth (35:10) What you’re next to matters (39:00) Rarity distorts value (39:53) Different cultures, different truths (43:10) Why philosophy starts with dissatisfaction (45:10) How far should skepticism go (49:40) Summary of nine skeptical modesDownload 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

Caleb and Michael delve into Plutarch’s insights on resisting social pressure, revealing that oversensitivity to shame is often at the root of being a pushover. They discuss historical examples of the dire consequences of conceding, like the stories of Creon and Medea. The hosts share practical strategies for building resistance, such as tackling social drinking and providing honest feedback. Humor is highlighted as a tool for tactful refusals, while they outline ten key reflections to help navigate societal norms without compromising personal integrity.

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. Others cut deeper - fortune can’t touch what matters most, which is yourself. The interesting part is watching someone work through these arguments for real, not as theory.(03:20) Historical context and influences(09:00) Book structure and Lady Philosophy(13:50) Fortune hasn’t changed, it was always fickle(16:40) You chose to value externals, don’t complain when they shift(18:40) Fortune gave you everything, can’t be mad it took it back(21:30) Don’t overweight current misfortune(29:30) Fortune can’t affect what matters - yourself(34:40) External riches aren’t valuable anyway(38:00) External honors aren’t valuable anyway(42:10) Preview of Book Three - defining the good(45:30) Final thoughts on the bookDownload 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

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: Finding Agency in Change (29:30) Combining the Whole and the Part (35:30) Athletes Who Can’t Let Go (39:50) Just Do What Nature Demands Now (43:30) Summary and SynthesisDownload 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

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