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

Trolleys, Torture, and Moral Dilemma’s (Episode 180)

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

Why Stoicism is False | Cicero's On Ends IV (Episode 179)

Living like a Stoic is about getting the little things right.  In this episode, Michael Tremblay discusses 7 Stoic habits you can start today to build a more thoughtful, resilient, and Stoic you.

(01:25) Thinking Well

(14:24) Living Philosophically

(17:58) Preparing for Adversity

(30:15) Summary

***

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

7 Stoic Habits You Can Start Today (Episode 178)

In this episode of Stoic Conversations, Caleb and Michael break down Book III of Cicero's On Ends - the definitive ancient defense of Stoic ethics.

Discover why the Stoics believed virtue alone is sufficient for happiness, and how they justified their unique system of values. Follow along as they unpack Stoic moral development, from our earliest instincts to the cultivation of wisdom.

On Ends Book I: The Epicureans [https://stoameditation.com/blog/the-epicureans-on-ends-book-i-episode-172/]

On Ends Book II: Against The Epicureans [https://stoameditation.com/blog/against-the-epicureans-on-ends-book-i-episode-175/]

(05:53) Overview Of The Book 

(09:34) Moral Development 

(26:46) Stoicism Defended 

(28:08) Morality is the Only Good 

(38:01) Indifferents 

(54:57) Awesome Lines

***

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

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 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/

The Classic Defense Of Stoic Ethics (Episode 177)

Seneca's brutal play "Medea" reveals what happens when rage takes control. A betrayed wife, an indecisive husband, and a tragic ending that challenges Stoic ideals.  

In this episode, Caleb and Michael analyze Seneca's bloody retelling of the Medea myth - where passion overcomes reason with devastating consequences.

Dana Gioia on Seneca and The Madness of Hercules (Episode 74) [https://stoameditation.com/blog/gioia/]

(04:28) Historical Background 

(06:43) The Story of Medea's Revenge 

(17:08) Character: Fortune Takes Wealth, Not Spirit

(21:27) Not Just a Moment's Madness 

(26:36) How Anger Warps Reality 

(33:44) Satisfying Madness

(36:02) The Intoxication of Rage 

(38:41) What's Up With Jason?

(46:03) Seneca's Court Experience 

(50:43) Brutal Ending: "There Are No Gods" 

(58:57) Outro

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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/

Seneca’s Medea | Revenge, Violence, and Stoicism (Episode 176)

Caleb and Michael take on Book II of Cicero’s On Ends.  In this books Cicero goes off against the Epicureans.  What do you think?

On Ends Book I [https://stoameditation.com/blog/the-epicureans-on-ends-book-i-episode-172/]

Aristippus: The Philosopher Who Mastered Pleasure [https://stoameditation.com/blog/aristippus-the-philosopher-who-mastered-pleasure-episode-167/]

(02:43) Different Kinds Of Pleasure

(16:34) Turning AgainstThe Stoics

(18:02) Ranking Pleasures

(24:40) Epicurean Rebranding?

(30:55) Epicureans Ignore Virtue

(34:28) Utilitarianism

(38:18) Topsy Turvy Value Systems

(46:50) Do Epicureans Lie?

(48:17) Is Happiness Up To You

(56:08) Michael's Takeaway

***

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

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

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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/

Against The Epicureans | On Ends Book II (Episode 175)

In this episode, Michael talks with Erick Cloward, the host of the Stoic Coffee Break Podcast.   Erick talks about his journey into Stoicism, his recent use of Amor Fati, and how to have difficult conversations, especially with those you politically disagree with.

(08:49) How Stoicism Makes A Difference 

(16:33) Amor Fati 

(31:03) Amor Fati And Politics 

(39:33) Hard Conversations 

(56:06) Bringing People Together 

(01:02:19) Learn More

***

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

Politics And Amor Fati With Erick Cloward (Episode 174)

Epictetus tells us the chief task of philosophy is just one thing: Make proper use of impressions.  

In this episode, Michael Tremblay does a deep dive into what this means, how we can do it, and why, for Epictetus, it is the most important thing there is.

***

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



Making Proper use of Impressions with Epictetus (Episode 173)

In 45 BC, amid the turmoil of the Roman Civil War, Cicero wrote one of philosophy's most important works on the meaning of life. This episode unpacks Book I of "On Ends," exploring the clash between Epicurean pleasure-seeking and Stoic virtue.

(01:14) Meeting Cicero

(06:18) Latin over Greek 

(11:40) On Ends Core Debates 

(16:03) Cicero attacks

(20:44) Why Pleasure isn't Everything 

(27:28) The Epicurean Response 

(31:29) Must Virtue Produce Something More? 

(46:53) The Epicurean View of Community 

(53:38) The Epicurean sage

***

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

The Epicureans | On Ends Book I (Episode 172)

Caleb and Michael discuess teacher of Diogenes and the grandfather of Stoicism. Before there were Stoics arguing about virtue, there was Antisthenes. A warrior turned philosopher who studied under Socrates.

(02:40) Antisthenes The Man

(07:32) Cynicism

(12:42) How To Become Cynical

(21:27) Virtue is Action

(23:58) Socratic Influence

(27:02) Antisthenes in Action

(29:38) Death

(34:34) Irreverance

(36:09) The Point of Philosophy

(39:08) Cynicism and Stoicism

***

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

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

The First Cynic | Antisthenes (Episode 171)

Caleb Ontiveros and Michael Tremblay discuss how to build resilience, develop virtue, and make sense of the world through Stoic philosophy.

One episode a week.

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Caleb Ontiveros

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