Stoa Conversations: Stoicism Applied

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

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 his ideas, from witnessing tyranny and democracy's failures in his youth to his later failed attempt to reform a Sicilian tyrant.Plato was an aristocrat who saw his relatives join the brutal Thirty Tyrants, watched democracy execute his mentor Socrates, and spent decades running a research academy that encouraged debate over dogma. His life and philosophy are worth understanding.(00:05:50) Plato's aristocratic background in Athens(00:06:30) The Thirty Tyrants and family connections(00:08:20) Socrates' execution and its impact(00:10:40) Key philosophical insights from political unrest(00:13:00) The Sophists reconsidered(00:19:20) Establishing the academy as research institution(00:21:00) Early, middle, and later period writings(00:27:20) Plato's caution about passive consumption(00:30:20) Criticism of poetry as ancient television(00:35:40) The religious dimension of Platonic philosophy(00:39:50) Return to Syracuse and the philosopher king project(00:47:40) Philosophy's ambitions beyond ivory towerDownload 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 breaks down the ten most important concepts you need to understand ancient philosophy's most practical school of thought.These are the core ideas that built a 2,000-year-old system for living well. From happiness and virtue to the dichotomy of control, each concept builds on the last to create a complete framework for human flourishing. (00:00:00) Introduction: Why These 10 Ideas Matter (00:01:50) Happiness and Flourishing (Eudaimonia) (00:02:50) Virtue as Excellence (Arete) (00:04:10) Knowledge as the Key (Episteme) (00:05:50) Living According to Nature (Kata Phusin Zen)(00:07:40) Mindful Attention (Prosoche) (00:09:20) Impressions and Assent (Phantasia and Synkatathesis) (00:11:00) The Things Up to Us (Ta Eph' Hemin) (00:12:20) Your Ruling Faculty (Hegemonikon) (00:13:50) Indifferents (Adiaphora) (00:15:40) Passions vs Good Emotions (Pathe vs Eupathe)(00:18:00) How the 10 Ideas Connect (00:21:40) What to Focus on NextDownload 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

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 performance in your job, relationships, or responsibilities seems to require abandoning virtue.Starting with Machiavelli's brutal advice to princes, they work through modern examples where this tension emerges. The activist who uses propaganda for a just cause. The CEO who fires employees for market efficiency. The lawyer defending someone they think is guilty. The journalist photographing tragedy without intervening.The Stoics said to follow your roles, but what if your roles demand cruelty, deception, or abandoning compassion? The conversation reveals three ways to think through these conflicts.(00:00) Introduction: When roles conflict with virtue(03:40) Machiavelli's challenge to virtue ethics(08:20) The difference between bad people and role conflicts(14:30) Modern examples: activists and propaganda(16:00) Workplace tensions: bosses and market demands(16:30) Impartial observers: journalists and philosophers(18:00) Best soldiers follow orders without question(20:30) Legal defenders and the guilty client(22:40) When roles seem necessarily at odds with virtue(27:00) Solution 1: The Stoic hierarchy of roles(30:00) Human role vs chosen roles(34:20) Why hierarchy alone isn't enough(38:50) Solution 2: Breaking virtue into sub-components(42:00) Fair dealing depends on context and circumstances(46:20) Practical advice for everyday conflicts(48:00) Solution 3: Using rights and consequences as constraints(50:40) Reserve clause and staying flexible between roles(51:20) Why most conflicts resolve with careful thinkingDownload 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

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 that made you invisible—if you could take, do, or have anything without consequence—what would you do? More importantly, what should you do?Michael explores what the Stoics believed about this thought experiment and what it reveals about their philosophy. 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

When life hits hard, where do you turn? Philosophy, therapy, or coaching? Michael and Caleb examine and debate the fundamental differences between these approaches to human suffering and growth.They explore why Stoicism offers a prescriptive vision of the good life while therapy remains deliberately non-judgmental. The conversation reveals when philosophy works best as preventative strength training versus therapy's role in acute crisis intervention.(00:00) Introduction: Philosophy vs Therapy(03:20) The Ancient Medical Metaphor(09:00) Different Goals: Prescriptive vs Non-judgmental(23:30) Stoicism as Preventative Training Only(27:30) When People Discover Stoicism After Crisis(32:20) Why Some Stoics Struggle with Crisis Moments(38:00) Questioning the "Solution" Mindset(42:10) Who Should Choose What Path(48:30) Practical Stoic Techniques in Daily Life(52:40) Knowing When You Don't KnowDownload 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

In this episode, Caleb and Michael review the 2023 film "Seneca, On the Creation of Earthquakes" starring John Malkovich. They explore how the movie portrays the Roman Stoic philosopher during his final day, examining themes of hypocrisy, performance versus genuine philosophy, and the challenges of living up to Stoic ideals.(00:00:56) Background on the film(00:04:07) Overall impressions(00:08:38) Play by play of the plot(00:13:58) Discussion of Agrippina's portrayal(00:16:31) Analysis of the Thyestes play scene(00:21:00) Examination of slavery themes(00:24:15) Seneca's hypocrisy and wealth(00:27:43) Seneca's death scene(00:30:06) Theme: Can you separate philosophy from philosopher?(00:35:15) Theme: What the film says about Stoicism(00:39:53) Theme: Criticism of pointless political art***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 you really be reading all those "great books"? Marcus Aurelius had strong opinions about this. He repeatedly told himself to throw away his books and stop getting distracted by endless reading lists.In this episode, Caleb challenges the popular Great Books movement and explores what Marcus Aurelius would think about our obsession with reading everything. The emperor-philosopher believed reading should transform you, not just educate you. He saw most reading as distraction from the real work of living.What do you think?***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

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 wise is literally insane.These weren't just philosophical word games. They were deliberate provocations designed to force people to think differently about what really matters in life.Caleb and Michael break down Cicero's six famous Stoic paradoxes and explain why each one makes more sense than it first appears. You'll discover how these seemingly absurd claims reveal the radical core of Stoic thinking.(01:41) Virtue is the only good(10:06) Virtue is sufficient for happiness(13:53) All good deeds are equally virtuous and all bad deeds are equally vicious(27:16) All fools are mad(33:32) Only the wise are free(38:16) Only the wise are rich(43:47) Summary***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

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 simplicity is dangerous.The dichotomy of control becomes the lens through which people view all of Stoicism. Get it wrong, and everything else falls apart. You end up passive when you should act, frustrated when you should be patient, or convinced Stoics can't believe in cause and effect.Michael and Caleb walk through four major misunderstandings that stem from getting the dichotomy wrong. From the myth that Stoics are passive observers to the confusion about free will and determinism, these mistakes reveal how a powerful idea can be corrupted when we bring our own assumptions to ancient wisdom.(04:15) Four Confusions(11:17) The Passivity Argument(19:08) Do You Have Immediate Control?(27:45) No Trichotomy(35:58) Is the Dichotomy Incompatible With Determinism?(41:00) Wrapping Up***Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribeDownload 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.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

Are you stressed about the future? Deep-dive into this Stoic exercise from Marcus Aurelius for living the moment, without anxiety or regret.Michael Tremblay covers the Stoic practice of circumscribing the present.***Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribeDownload 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/Check out our Youtube: https://www.youtube.com/@stoaphilosophyThanks 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

Discover the philosopher who transformed Zeno from shipwrecked merchant to Stoicism's founder. While modern cynics see only self-interest, Crates lived joyfully with nothing but "a wallet and tattered cloak." This philosopher sold his inheritance, mocked social hierarchies, and treated everyone as equals—from generals to donkey drivers.Michael and Caleb explore how Crates' rejection of convention shaped Stoic philosophy. They examine the benefits of temporarily embracing cynical minimalism as a path to wisdom and why Epictetus admired these philosophical outsiders. A look at the roots of Stoic thought and the value of questioning everything.Evolve Magazine – Cultivating Wisdom and Virtue(03:05) Zeno and Crates(05:11) Crates Life(10:32) What's the point of studying philosophy(12:00) Cynic Reject of Stoicism(16:56) Flatterers(18:27) Everyone Has Flaws(19:48) Insults(21:53) Hipparchia(27:33) Joyous Philosophy(29:55) Hardcore Stoicism(32:40) Benefit of Cynicism***Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribeDownload 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.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