Stoa Conversations: Stoicism Applied

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 c...

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. *** Downloa...

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, y...

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 tension...

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 *** Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources...

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...

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) (04:28) Historical B...

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 Aristippus: The Philosopher Who Mastered Pleasure (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 Val...

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) Bringin...

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. *** Download the Stoa app (free): https://stoameditation.com/pod For those who find the app valuable but face financial constraints, email us f...

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 Epi...

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 (3...

Freedom isn't about having enough money to do what you want. It's about wanting what you can actually control. In this episode, Michael breaks down Epictetus's radical handbook chapter 14, revealing the four key principles of Stoic desire – and why wanting the wrong things makes us slaves to circumstance. *** Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic...

The ancient Stoics never used the term "metacognition," but this modern psychological concept illuminates the core of their philosophy. Michael and Caleb explore how the Stoic emphasis on examining our thoughts—what psychologists now call metacognition—is central to both Stoic theory and practice. They unpack why the Stoics saw this capacity for mental self-reflection as divine, how it distinguish...

Ancient and modern Stoics aren't just thinkers - they are runners too. In this episode, Caleb explores how the simple act of running illuminates core Stoic principles about pain, perception, and perseverance.  *** Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: www.stoaletter.com/subscribe Download the Stoa app (it’s a free download): https://st...

Meet ancient Greece's original hedonist. Unlike later philosophers who preached asceticism, Aristippus embraced luxury, courted kings, and still kept his freedom. A student of Socrates who chose pleasure over asceticism, he founded a school of thought that spread through generations of his family. This conversation explores how Aristippus balanced the pursuit of pleasure with self-mastery, challen...

In this episode, Michael and Caleb explore Meditations 4.49-51, where Marcus Aurelius discusess resilience, misfortune, death, and simplicity. Be like a promontory against crashing waves. (01:09) 49, Section 1 (08:20) 49, Section 2 (11:21) It's Not Things Themselves That Harm Us (15:44) Powerful Phrases (17:45) Stoicism Is For Everyone (21:21) 50 (33:39) 51 *** Subscribe to The Stoa Letter for wee...

Goodhart’s Law says: when a measure becomes a target, it ceases to be a good measure.  But if that’s true, how should we measure our philosophical progress?  In this episode, Michael Tremblay wrestles with this question. *** Download the Stoa app (free): https://stoameditation.com/pod For those who find the app valuable but face financial constraints, email us for a free account. Listen to more ep...

Get these tested Stoic strategies pull you out of bed and back into life's beauty. Michael and Caleb explore ancient wisdom for reconnecting with meaning through nature, duty, and proper thinking. (00:47) Set Up (04:33) Crisis in Thinking (10:29) Finding Purpose (19:18) Beauty (26:59) Play With Time (38:43) Be Gentle (42:08) Summary *** Download the Stoa app (free): https://stoameditation.com/pod...

No one chooses to be wrong. This core Stoic teaching, inherited from Socrates, shaped how ancient philosophers viewed human behavior and mistakes. In this episode, Caleb explores why the Stoics believed people only do what they think is best – even when those choices seem obviously wrong to others. The episode tackles challenging questions: How do addictions and bad habits fit into this framework?...

Pain is inevitable. Suffering is optional. In this episode, we explore a powerful Buddhist concept that mirrors Stoic wisdom: the Second Arrow. The first arrow is the pain life throws at us - rejection, loss, failure. The second arrow? That's the one we shoot at ourselves through our reactions, stories, and judgments. Michael Tremblay discusses the Buddhist parable of the second arrow and what it...

Author and Podcaster Noah Rasheta explores the parallels between Buddhism and Stoicism with Michael Tremblay. Whether you're seeking practical wisdom or philosophical insight, this conversation offers tools for living more skillfully – regardless of which tradition resonates with you. From handling grief and identity to achieving wisdom, we uncover where these philosophies converge and diverge. No...

Caleb and Michael discuss Stoic epistemology—how to think well, avoid ignorance, and form justified beliefs. They explore the importance of skepticism, setting realistic standards for truth, and cultivating expertise to navigate complex decisions. (00:00) Common Sense (04:54) Default To Skepticism (09:38) Criterion of Truth (18:31) Common Sense (29:10) Building Confidence Through Expertise  (35:01...

Caleb Ontiveros makes the case that Stoicism is more intuitive than you might think. He argues that if minor setbacks don't ruin our lives, why should major ones? This episode explores how Stoic ideas about virtue, happiness, and adversity align with our deepest intuitions about living well. *** Subscribe to The Stoa Letter for weekly meditations, actions, and links to the best Stoic resources: ww...

Bryan Caplan, economist and bestselling author, discusses practical wisdom from modern economics and ancient philosophy. He argues against medicalization of human behavior, champions personal agency, and reveals why appeasement often beats confrontation. Caplan shows how lessons from economics can serve as self-help and why creating a "social bubble" – the modern version of an Epicurean garden – m...