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 n…

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 enemie…

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 wrongdo…

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 …

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 th…

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 meditation…

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 in…

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 Madne…

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 Virtu…

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 Politic…

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 val…

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…

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) Antisthe…

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…

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 me…

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 Downloa…

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 …

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 (…

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…

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 th…

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 …

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…

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…

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…

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, …

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 bubbl…

Michael and Caleb explore how understanding ourselves as our faculty of choice—not our bodies, possessions, or reputation—transforms our approach to life's challenges. Learn how clarifying what we are (and aren't) guides self-improvement and decision-making, unlocks insights in Stoic theory, and ultimately leads to a more tranquil existence. (06:10…

Why Epictetus tells us to compare our suffering to others. This simple exercise can help you in times of crisis. Join Michael as he breaks down Epictetus’s Handbook 26. *** 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): h…

Has Science proven that the world is nothing more than a physical machine without overarching purpose? Spencer Klavan’s most recent book answers with an emphatic no. Ancient philosophy and modern science reveal that the worldview of materialism is not enough. Instead, our picture of the world must include mind as a fundamental ingredient – just as …

What if the things you obsess over daily don't ultimately matter? The ancient Stoics had a radical idea: most of what we chase - wealth, fame, even health - is neither good nor bad. They called these things "indifferents." In this episode, Caleb reads his short piece on indifferents and adds additional commentary. Read the piece: https://www.stoale…

In this episode, Michael and Caleb break down Handbook 42, where Epictetus lays out Socratic Intellectualism and explains why people's harsh words say more about them than you This episode will challenge your assumptions about conflict and equip you with practical Stoic tools for navigating a world of criticism and misunderstanding. (00:52) Epictet…

Money talks, but what do the Stoics say about it? In this episode, Caleb and Michael dive into the relationship between Stoicism and wealth. They explore the risks of chasing riches, the virtue of moderation, and why philosophy should come before your bank account. You'll hear Epictetus' take on why honesty trumps money-making and Seneca's surprisi…

Michael talks with Brigid Delaney about her journey into Stoicism, the value it has had in her life, and the unique role it has to play in helping others. Reasons Not To Worry (03:41) Stoicism vs Wellness (13:15) Ataraxia (18:07) Stoic Friends (20:26) Favorite Stoic (24:14) How To Explore The Stoics (29:47) Persauding Non-Stoics (34:11) Stripping A…

The four pillars of Stoic Justice. Justice isn't just about courtrooms and laws. For the Stoics, it was a way of life. In this episode, Caleb and Michael break down the four components of Stoic justice: piety, kindness, good fellowship, and fair dealing. They explore how these ideas apply to our lives today, from helping strangers to making tough b…

Blushing, sweating, stumbling over words - we've all been there. But what if these physical reactions are holding you back from greatness? In this episode, Caleb and Michael unpack Seneca's advice on handling embarrassment like a Stoic. (00:46) Embarrassing Introduction (04:50) Seneca On Blushing (08:08) Feelings vs Judgments (10:02) You Are Not A …

In this episode, Caleb and Michael explore how Stoicism reframes our understanding of risk, teaching us to embrace uncertainty while focusing on what truly matters. They discuss: Why Stoics aren't reckless, but cultivate caution How Stoicism offers the highest reward with the lowest real risk Critiques that Stoicism is for the risk-averse, and why …

Is Stoicism just toxic positivity? No, obviously. But what's the difference between toxic positivity and unrealistic optimism? And how can Stoics avoid the real risks of both? In this episode, Caleb and Michael dive deep into Stoic practice and its alleged similarity to toxic positivity. *** Listen to more episodes and learn more here: https://stoa…

The Stoic art of solitude and self-consistency Can you be alone with your thoughts? Seneca's Letter X challenges us to master the art of solitude. In this conversation, Caleb and Michael unpack Seneca's advice on solitude and explore its relevance in our hyperconnected world. (00:58) The Paradox of Solitude (05:40) Consistency Between Private and P…

Join Caleb and Michael as they dissect the mental game of competition and explore how ancient philosophy can give us an edge in modern battles – both on and off the mat. In this gripping episode, Caleb shares his experience competing in his first Brazilian Jiu-Jitsu tournament and the valuable lessons he learned about applying Stoic principles unde…

Diogenes: the man who lived in a barrel and inspired Stoic philosophy. In this episode, Michael and Caleb explore the life and ideas of Diogenes the Cynic - one of the most influential and eccentric philosophers of ancient Greece. They discuss: (00:00) Epictetus on Diogenes' Freedom (03:21) Diogenes' Life and Connection to Stoicism (08:29) Diogenes…

Caleb Ontiveros speaks with Johnathan Bi, an entrepreneur and philosopher, about Friedrich Nietzsche's critique of Stoicism and egalitarianism. The conversation begins with Jonathan sharing his personal journey from STEM to philosophy, setting the stage for a deep dive into Nietzsche's challenging ideas. They explore Nietzsche's opposition to Stoic…

In this episode of Stoic Conversations, Michael Tremblay offers a deep dive into one of Stoicism's most popular concepts: the Dichotomy of Control. Drawing from his 2021 article for the Modern Stoicism blog, Tremblay explores common misunderstandings about this principle and provides a more nuanced interpretation aligned with authentic Stoic philos…

Should Stoics become rich? What is your relationship to money? Caleb speaks with Darius Foroux about his new book The Stoic Path To Wealth. They discuss a practical investment strategy and how Stoics should think about investing. https://dariusforoux.com/ https://stoicpathtowealth.com/ (00:50) Darius's Story (04:32) Stoicism (11:51) Your Relationsh…

The ancient Stoic, Arius Didymus, provided a framework for practical wisdom and prudence. It’s still applicable today. Courage Moderation (02:29) Reading (05:01) Judgment (17:19) View (26:24) Shrewdness (31:11) Discretion (37:38) Soundness of aim (41:31) Resourcefulness *** Subscribe to The Stoa Letter for weekly meditations, actions, and links to …

Michael and Caleb discuss the differences between modern self help and Stoicism – where self help is useful, where it isn’t, and recommend their favorite self help books. (04:07) Defining Self Help (11:31) Where Self Help Goes Wrong (28:09) The Good in Self Help (45:02) Best Self Help Books *** Download the Stoa app (it’s a free download): stoamedi…

Caleb and Michael read through Marcus Aurelius’s Meditations. Specifically: Meditations 2.6-2.10. There are several essential themes in these passages: the importance of self-examination, maintaining focus on what matters, and the philosophical underpinnings of Stoicism. in the Meditations we get to see Marcus Aurelius rehearsing Stoic maxims – and…

This one is different. Caleb reads from his essay, Why Stoicism Is True. It’s a short encapsulation of the what he takes to be the three most important ideas of the philosophy – as well as a philosophical defense of their veracity. Let us know what you think. https://calebontiveros.substack.com/ *** Download the Stoa app (it’s a free download): sto…

In this episode, Michael presents the Stoic idea of "indifferents." It’s one of the key ideas behind Stoicism, one’s that often misunderstood but necessary to know in order to understand Stoicism. (02:52) The 3 Value Categories (06:22) Defining Good (15:32) Defining Indifferents (37:32) Total Indifferents (39:06) How To Live With Indifferents (51:2…

“Moderation is subdivided into good discipline, seemliness, modesty, and self-control.” The ancient Stoic breakdown of moderation is essential for becoming more disciplined. It will help you think about the ideas of moderation, discipline, and self-control more deeply and generate strategies for how to becoming more moderate in your life today. Sto…

In this conversation, Michael and Caleb discuss Epictetus’s chapter On Attention (Discourses 4.12). It’s an essential reading from the Stoic master on an essential topic. Buddhism 101 Stoicism and Mindfulness Caleb and Michael also preview an upcoming conversation on Moderation…Stay tuned. It will be released in the next few weeks. (01:04) The Impo…