Stoa Conversations: Stoicism Applied

Caleb
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Oct 21, 2025 • 49min

Eclecticism with Anya Leonard from Classical Wisdom (Episode 206)

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
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Oct 14, 2025 • 8min

Hunters Talk About Spears (Episode 205)

Discover why focusing on mechanisms is key for change, as aspirations often lead to inaction. The metaphor of hunters discussing spears illustrates the importance of practical philosophy. Learn how to break down virtues into actionable parts, making ethics relevant in daily life. Explore the balance between training and performance in Stoic practices. The key takeaway? Aspirations guide your goals, while concrete mechanisms drive your success!
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10 snips
Oct 7, 2025 • 50min

Stoicism, Freedom, and Ernst Jünger with Sam Alaimo (Episode 204)

Sam Alaimo, a former U.S. Navy SEAL and co-founder of Zero Eyes, dives into fascinating discussions on Stoicism and its relevance in affluent societies. He shares how Stoicism helped him transition from military life and critiques AI as a potential threat to human reasoning. Alaimo also explores the complex philosophy of Ernst Jünger, examining his wartime experiences and literary contributions. The dialogue traverses ancient philosophy, the essence of freedom, and the tension between virtue and practicality, making for an intriguing listen.
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Sep 30, 2025 • 55min

Ancient and Modern Myths with Michael Fontaine (Episode 203)

Michael Fontaine, a classics professor at Cornell University and author of 'How to Have Willpower,' explores the intersection of ancient wisdom and modern myths. He discusses the three ancient models for mental suffering: medical treatment, spiritual purification, and personal responsibility. Fontaine contrasts these with contemporary psychiatric approaches. He also delves into Stoic and Epicurean views on virtue, death, and the nature of the mind, urging listeners to embrace ancient philosophies for modern self-empowerment and flourishing.
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6 snips
Sep 23, 2025 • 12min

Anger And Society (Episode 202)

Caleb delves into the intriguing concept of anger as social currency. He discusses how failing to express anger might signal indifference, raising questions about emotional expectations in relationships. The podcast examines anger's role as a political tool and a tribal signal. Listeners learn that Stoics face the challenge of demonstrating care through actions rather than emotions. Discover how managing emotions is just the first step in navigating social dynamics.
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Sep 18, 2025 • 1h 14min

Stoicism & Anger w/ Donald Robertson

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
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10 snips
Sep 16, 2025 • 21min

Two Practices For Zen Stoicism (Episode 201)

Explore the fascinating intersection of Zen practices and Stoicism! Learn about alert observation—watching your thoughts without getting caught up in them. Discover the power of cessation, where a simple pause can clear your mind from clutter. Insights from Marcus Aurelius emphasize the importance of monitoring thoughts and dismissing false judgments. This conversation promotes a mindful approach to decision-making, steering clear of distractions and focusing on what truly matters in life.
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Sep 9, 2025 • 50min

Should Stoics Use AI (Episode 200)

The podcast dives into whether Stoics should embrace AI, balancing ancient wisdom with modern technology. It discusses the dangers of overconfidence and the importance of discernment when using AI as a tool, rather than a crutch. Key insights reveal how AI mirrors human intellect, emphasizing the need for genuine understanding and self-mastery. The conversation also explores AI’s role in cultivating relationships, and the ethical considerations of integrating these technologies into our lives, encouraging a reflective and prudent approach.
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Sep 2, 2025 • 34min

Stoic Exercise Tier List (Episode 199)

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
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Aug 26, 2025 • 59min

Effective Altruism as a Life Philosophy (Episode 198)

Delve into the nuanced world of effective altruism, where helping others is seen as an optimization problem. Can you truly do good if it's not impactful enough? The hosts discuss Peter Singer's morally charged drowning child argument, questioning our obligations to help. They also tackle the superhero efficiency problem, pondering whether boring, high-impact careers might be more heroic than traditional acts of valor. The philosophical clash between effective altruism and Stoicism reveals deeper truths about moral duty and community connections.

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