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 a...

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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/pod If you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up wit...

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....

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 m...

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. Other...

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...

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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...