Stoa Conversations: Stoicism Applied

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

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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

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Thanks to Michael Levy for graciously letting us use his music in the conversations:

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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.

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Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Check out our Youtube: https://www.youtube.com/@stoaphilosophy

Thanks to Michael Levy for graciously letting us use his music in the conversations:

https://ancientlyre.com/

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

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Thanks to Michael Levy for graciously letting us use his music in the conversations:

https://ancientlyre.com/

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 as much as doing the right thing, and how this ancient framework applies to modern life.

The conversation unpacks key concepts from Aristotle's Nicomachean Ethics: habituation, the role of pleasure in virtue, and why context matters in ethical decisions.

(08:29) Aristotelian Happiness

(10:47) Parts of the Soul

(12:44) The Kinds of Virtues

(14:04) Virtue as Skill

(18:39) Habituation

(19:42) The Golden Mean

(26:07) Good Reason For Bad Feelings

(28:24) Meaning of Virtue

(31:37) Self-Reinforcing Virtue

(35:31) What the Golden Mean Means

(45:02) Key Ideas For Practice

(48:03) Differences with Stoicism

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Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Check out our Youtube: https://www.youtube.com/@stoaphilosophy

Thanks to Michael Levy for graciously letting us use his music in the conversations: https://ancientlyre.com/

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 (where virtue alone brings happiness) and Aristotle's elitism (where external goods are required).

(01:53) Awesome Beginning

(07:10) What's Our Purpose?

(26:09) Supreme Happiness

(31:55) Cicero's Objection

(40:39) Summary

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Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribe

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Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Check out our Youtube: https://www.youtube.com/@stoaphilosophy

Thanks to Michael Levy for graciously letting us use his music in the conversations: https://ancientlyre.com/

Discover the hidden gems of Stoic philosophy in this exploration of Epictetus' fragments - those powerful passages preserved by other philosophers but lost from his main works.

Caleb and Michael unpack these concentrated nuggets of wisdom, from the surprising idea that we should value people by their capacity to help friends rather than harm enemies, to the famous "persist and resist" maxim that captures the essence of Stoic emotional management.

Learn why terrible people are already punished by their own character, how to judge humans by their true virtue rather than superficial success, and why no one is truly free without mastering themselves.

(00:00) MT: Fragments 

(05:18) Fragment 7: Helping Friends vs. Harming Enemies 

(10:43) Fragment 10: The Clean Jar - Approaching Philosophy Properly 

(16:19) Fragment 10: The Famous "Persist and Resist" Maxim 

(19:31) Fragment 13: Why Bad People Are Their Own Punishment 

(25:39) Fragment 18: Judging Humans by Their True Excellence 

(28:41) Fragment 17: The Banquet of Life 

(31:29) Fragment 20: Becoming Resilient to Emotions 

(37:04) Fragment 26: A Soul Carrying a Corpse 

(39:39) Fragment 35: True Freedom Through Self-Mastery

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Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribe

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Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Check out our Youtube: https://www.youtube.com/@stoaphilosophy

Thanks to Michael Levy for graciously letting us use his music in the conversations: https://ancientlyre.com/

In this episode, Michael Tremblay explores Epictetus' radical approach to anger and forgiveness. Discover why the Stoics believed we should pity rather than punish those who harm us, and how this ancient wisdom offers a practical path to emotional freedom in your daily life. Through Epictetus' teachings, learn the liberating power of seeing wrongdoers as victims of their own confusion.

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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/

Michael and Caleb dive into classic philosophical thought experiments to uncover Stoic solutions to impossible choices. From the infamous Trolley Problem to the Happiness Machine, they examine how Stoicism's focus on virtue, context, and roles provides a unique framework for moral decision-making.

Unlike utilitarian or rule-based ethics, the Stoic approach emphasizes character over consequences, yet remains practical when facing life's hardest choices. This thought-provoking conversation challenges modern assumptions about ethical reasoning while revealing surprising Stoic positions on torture, self-sacrifice, and artificial pleasure.

(01:57) Trolley Problem

(14:35) Do Stoics Endorse Torture?

(20:31) Happiness Machine

(24:24) Utility Monster

(27:14) Euthyphro Dilemma

(35:53) Sinking Ship

(40:59) Prisoner's Dilemma

(46:11) Omelas Child

(53:59) Takeaways

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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/

Caleb and Michael break down Book IV of Cicero's "On Ends" - his powerful critique of Stoic ethics.

Discover why Cicero believed the Stoics fell short by prioritizing virtue alone while dismissing external goods. 

Is Stoicism just playing word games with what's "good" versus "preferred"? Would the perfect Stoic and the perfect Aristotelian behave the same way? This episode tackles the core tensions in ancient ethics that are relevant for modern life.

(03:22) Cicero's Perspective

(07:51) Weak Arguments

(08:44) Powerful Argument #1 – Stoicism Wasn't New

(16:16) Powerful Argument #2 – We Have A Body

(22:22) Powerful Argument #3 – The Dilemma

(33:27) Defending Stoicism from #3

(48:30) Taking On Argument #2 

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Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribe

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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/