Stoa Conversations: Stoicism Applied

Caleb
undefined
Nov 11, 2025 • 48min

How to Face Hardship | Boethius and The Consolation of Philosophy (Episode 209)

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
undefined
Nov 4, 2025 • 45min

Dealing with Change (Episode 208)

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
undefined
Oct 28, 2025 • 46min

Ask Us Anything (Episode 207)

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
undefined
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
undefined
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!
undefined
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.
undefined
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.
undefined
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.
undefined
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
undefined
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.

The AI-powered Podcast Player

Save insights by tapping your headphones, chat with episodes, discover the best highlights - and more!
App store bannerPlay store banner
Get the app