Stoa Conversations: Stoicism Applied

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 Stoi...

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 Stoi...

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...

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...

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 Robert...

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 notic...

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 Stoi...

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=ios Michael 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...

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 argume...

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) Prac...

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 ga...

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 Socrate...

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 (...

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...

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 phil...

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 train...

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 (00:08:3...

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 re...

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...

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 St...

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/subscribe Download the Stoa app (it’s a free download): https...

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...

In this episode, Michael Tremblay and Caleb Ontiveros explore Aristotle's ethics, focusing on his doctrine of virtue as the golden mean. They break down how Aristotle's view differs from Stoicism—from his three-part soul to his idea that virtues are skills developed through practice. Learn why Aristotle saw courage as a balance between cowardice and rashness, why feeling the right emotions matters...

In this final exploration of Cicero's "On Ends," Michael and Caleb break down Book V, where Cicero reveals his own philosophical sweet spot – an Aristotelian-Platonic approach that challenges both Stoicism and Epicureanism. Against a backdrop of ancient Athens, Cicero's characters debate the core question: What makes a truly good human life? They navigate the middle path between Stoic rigidity (wh...