Stoa Conversations: Stoicism Applied

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 are objectively better than others. And no one truly wants to do evil.(00:00) Politics can’t make you unhappy.(09:00) Anger is never appropriate.(19:40) Neither victimhood nor victory are moral credentials.(26:10) You don’t choose all your roles.(34:20) Nearly everyone today lives in luxury.(39:10) Some lives are better than others.(43:10) No one intends to do evil.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

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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

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 murdered dinner guests. The key insight is that caving makes things worse while standing firm with tact makes things better.(04:47) The Pushover: Oversensitivity to shame versus shamelessness(12:20) Mythical and historical examples of caving to pressure(22:20) Starting small: Rejecting social drinking and suffering fools(26:10) Giving honest feedback despite discomfort(32:10) Ten reflections on resisting pressure(41:30) Personal examples of caving and standing firm(43:40) Rules for not giving inDownload 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

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

How much ancient philosophy should you steal? Caleb and Anya Leonard from Classical Wisdom explore the art of philosophical eclecticism, from Heraclitus’s cryptic fragments to philosophical rivals between Stoics and other schools.We start with Heraclitus, the riddling philosopher who wrote that you can’t step in the same river twice. His idea that strife creates harmony deeply influenced the Stoics. But he was deliberately obscure - even Socrates admitted he needed a “deep diver” to understand him. From there we discuss Skepticism and Epicureanism. (00:03:57) Flux and constant change(00:12:24) Providence vs chaos(00:15:21) Is strife justice(00:21:30) Fragments worth contemplating(00:22:41) Skepticism: How we know what we know(00:29:00) The Stoic-Skeptic debate(00:31:00) Suspending judgment in heated times(00:35:28) Epicureans and calculated pleasure(00:39:00) Simple pleasures vs hedonism(00:44:22) The value of eclecticismDownload 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

Philosophy talks about big ideas. The good life. Virtue. Happiness. But talking about aspirations isn’t enough. You need mechanisms—concrete practices that actually change behavior.Caleb examines why serious thinkers focus on mechanisms over aspirations. Discussions about mechanisms force action and generate information. Discussions about aspirations turn into complaints about the world.The Stoics were good at this. They didn’t just discuss anger. Seneca and Marcus Aurelius gave specific advice about becoming less angry. They broke virtue down into smaller parts: self-control becomes orderliness, propriety, modesty, self-mastery. Each breakdown gets more specific and decision-relevant.But you can’t ignore aspiration entirely. You need both the effective cause (what brings about change) and the final cause (where you’re going). Training and performance. The concrete and the universal. The Stoic sage sees and acts with both the whole and the part in mind.Philosophy is tricky because the problems are abstract. But that’s exactly why you need to speak at the right level of detail. Mechanisms for a purpose. Aspirations to set the target. Concrete practice to get there.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

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 writes at whatthen.org. Caleb and Sam discuss how affluent societies need philosophy, whether virtue alone makes life good, and why Ernst Jünger remains one of history’s most fascinating thinkers. The conversation moves from ancient philosophy to World War I trenches to the risks of letting AI do our thinking.(00:00) Sam’s background and writing journey (04:00) How Stoicism helped after military service (06:20) Why affluent societies invented Stoicism (08:00) AI as a war on human reason (10:30) Epictetus: the most extreme example (15:00) Marcus Aurelius: emperor and philosopher (20:10) Why Epictetus avoided the word “virtue” (24:10) Stoicism as energetic, not passive (26:20) Where the Stoics got it wrong (30:20) Existentialism and Stoicism on freedom (34:20) Ernst Jünger: war hero and philosopher (38:20) Storm of Steel and phenomenology of war (44:30) Philosophy divorced from reality (47:20) Jünger’s fiction and diariesDownload 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

Have we traded ancient wisdom for modern myths?In this episode, Caleb speaks with Cornell classics professor Michael Fontaine.Fontaine argues that psychiatry and mythology both offer competing stories about human suffering. The ancients had three models: medical treatment, spiritual purification, or taking responsibility for your choices. Today we’ve mostly picked door number one and forgotten the rest.How to Have Willpower(9:20) A Forgotten Distinction: Reasons vs Causes(19:30) Freedom and Responsibility(31:20) Death, Souls, and Scientific Myths(49:30) Ancient Philosophy for Secular StudentsDownload 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 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 wrong to read meaning into your emotional responses. If most angry people care and most calm people don't, anger becomes useful data. The Stoic who stays calm has to work harder to prove they care.(00:00:00) Introduction and context from Donald Robertson episode(00:02:10) Anger as social emotion vs internal emotions(00:03:10) Political case study: anger as tribal signal(00:04:50) How anger serves as political signaling(00:05:10) Social incentives to express anger(00:06:00) The difference between expressing and feeling anger(00:07:00) When loved ones expect your rage(00:07:20) The logic of anger as caring(00:08:00) Why people use emotional heuristics(00:09:40) How Stoics must prove they care(00:10:00) The burden of showing character through actions(00:10:40) Why managing emotions is just the beginningDownload 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 interview Donald J. Robertson on Anger and Stoicism.We’ll be doing more live events and chats. Get the Substack app and stay tuned. Get full access to The Stoa Letter at www.stoaletter.com/subscribe

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 figured this out centuries ago.Caleb explores two Zen practices that Stoics can steal. The first is alert observation: notice thoughts when they arise, then let them pass without getting caught up in them. Don't fear thoughts—just don't be slow to notice them.The second is cessation: when your mind gets worked up about something, stop immediately. Be like incense burning in an empty temple. Better to know you don't know than to have false opinions.Marcus Aurelius did something similar. He ruthlessly monitored his thoughts and dissolved the false ones. Most of our value judgments concern trivial things—popularity, pleasure, avoiding discomfort. These judgments pull us away from what actually matters: making excellent decisions based on reason.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

Should Stoics use AI? Michael and Caleb tackle this modern question by examining how ancient philosophy guides our relationship with new technology. They explore the risks of overconfidence, the difference between knowledge and mere reminders, and when AI becomes a useful tool versus a dangerous crutch.The conversation reveals why Plato's concerns about writing still matter today and how the Stoic concept of "digesting theory" applies to our AI-assisted lives. They examine practical examples from programming to philosophy, showing when AI helps and when it hinders genuine learning.Overconfidence and the Conceit of Learning(03:14) AI and overconfidence risks(12:40) Writing as a tool to avoid overconfidence(18:30) AI and digesting theory(24:50) AI as indifferent external(34:40) Stoics against AI friends(41:30) AI as mirror of the logos(45:20) The virtue of prudence with AI(48:30) Closing thoughts on major technology shiftsDownload 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 going live with Donald J. Robertson this Thursday at 5 PM ET. Join us on the Substack app!https://open.substack.com/live-stream/53794?r=5jw33r&utm_medium=iosMichael ranks ten core Stoic exercises from least to most transformative based on a decade of practice. One could say he cuts through the theory to share which techniques actually work.All of these practices are good. But Michael uses some more than others.(00:00) Introduction: Personal ranking vs universal truth(03:00) Lower tier exercises(11:40) Middle tier practices(20:00) Top tier transformative practicesDownload 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

Can you do good and do it wrong? Michael and Caleb examine effective altruism - the movement that treats helping others like an optimization problem.They explore how EA demands you maximize impact rather than feel good about helping. The conversation reveals why Superman should probably quit fighting crime and start generating renewable energy instead.(03:10) Peter Singer's drowning child argument(09:00) Internal consistency as moral demand (16:10) Science-based approach to doing good(19:30) 80,000 hours and high-impact careers (23:40) Why boring work might be more heroic (28:00) Truth-seeking versus feeling good (34:20) The superhero efficiency problem(34:50) Shared cosmopolitan values (37:40) Different approaches to transformation(43:40) Extreme versus rooted cosmopolitanism (49:40) Status quo bias and tradition (56:50) The beneficence challenge to StoicsThe Stoa Letter is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.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

How memory and diet shape your character. Andrew Perlot , former journalist and health coach, explains why the Stoics obsessed over both.(00:00:56) What Stoicism is and why Andrew is drawn to it(00:05:32) Favorite Stoic philosophers(00:09:00) Diet and Stoicism(00:21:10) Why religious groups like Seventh Day Adventists succeed with diet(00:24:30) Shame vs virtue in food choices(00:29:20) Practical tips: simple foods and fasting(00:33:24) Stoicism and memory(00:39:40) Why the Stoics literally meant "memorize this"(00:43:00) How to remember: Method of Loci(00:48:40) Memory as forcing function for focusDownload 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 explore Takuan Soho's The Unfettered Mind, examining how Zen Buddhism approaches mental training through the concept of "no mind." They discuss why stopping the mind creates ignorance and how this differs from Stoic approaches to reason and attention.They examine how mental stopping manifests in combat, conversation, and performance - from sword fighting to basketball arcade games.(00:00) Introduction to The Unfettered Mind(06:20) The Affliction of Stopping(14:47) The Beginner vs The Expert(27:22) Training(37:22) Practical Life(43:53) Stoicism vs ZenDownload 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