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…

Do we have free will or are we destined to our fate? Do the Stoics believe that we have free will or are our lives pre-determined? Does is matter? Today I’m going to talk about the Stoic ideas behind free will and fate, and how it does or doesn’t impact our lives. “Lead me, Fate, wherever you will, and I will cheerfully follow. For even if I kick a…

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…

What if I told you that the thing you’re avoiding… is exactly the thing you need most? Today we’re going about why comfort might be the biggest lie we believe, and how leaning into resistance can actually be the path to everything you want. “The superior man thinks always of virtue; the common man thinks of comfort.” ― Confucius Send us a text My b…

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…

In this week's episode, I take some time to answer a few questions: - What should I do when someone criticizes me and I know they’re right? - How do I know if I’m actually making progress in my personal growth—or just spinning my wheels? - What would Marcus Aurelius say about social media? - What’s one way I secretly avoid discomfort—even though I …

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…

Empathy has been called everything from a virtue to a weakness to a sin. But in an age of outrage, is empathy a liability? Or is it the very thing we need to preserve civilization? In this week's episode I talk about the importance of empathy and why we need more, not less empathy in the world. “Wherever there is a human being, there is an opportun…

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…

The Stoics place a premium on rationality and objectivity to help manage our emotions. But how do we develop that objectivity? Why should we practice become more objective? In this week’s episode we’re going to dive into those questions and talk about how you can be more objective. “Between stimulus and response, there is a space. In that space is …

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…

What if your biggest obstacle in life isn’t a lack of knowledge, but something else? What if this one attribute is the one thing that can help you truly excel in life? In this episode, I want discuss what I think is the greatest attribute that any person should have who wants improve themselves and how to develop it. “I’m am neither clever nor espe…

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…

How often to you spend time worrying about everything that is happening in the world? How can you create more joy into your life? Can a Stoic be happy and joyful? Today I want to talk about Stoicism and joy. “A cheerful disposition and serenity of mind are not the result of luck but of wisdom.” — Seneca (Here's the link to the sunshine video!) Send…

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 times of political division, it’s easy to be swept away by anger, resentment, and fear. But what does that accomplish? Does your anger towards those that disagree with you help yourself or the world? In this episode I want to talk about the importance of maintaining your Stoic principles in times of turmoil. “The essence of good and evil consist…

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…

Stoicism is a very personal and practical philosophy. But what would a company look like that implemented some of the ideas from Stoic philosophy? In this episode, I interview Geoff Roberts the CEO of Outseta. Many of the operating principles run counterintuitive to the conventional wisdom of how most companies are managed, and they've been quite s…

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…

Are you happy? Do you struggle when life doesn’t go the way you want? Today I want to talk about why we as humans are great at making ourselves unhappy, and some ideas the Stoics gave us to make our lives better. “Man is not disturbed by things, but by the views he takes of them.” — Epictetus Send us a text My book Stoicism 101 is available! Order …

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…

This weeks episode is an interview with Dr. Erik Fisher. Erik is the host of the Emotional Algebra podcast, and works with patients and clients to manage their emotions in a way that is very similar to Stoicism. We had a great and wide ranging conversation about emotions, trauma, and how become more emotionally resilient. Send us a text My book Sto…

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…

Are you confused about the different teachings of Stoicism you find on the internet? Would the Stoics advocate for the “hyper-masculine” culture that uses Stoicism to support some approaches to stress, dating, and how to treat others? Today I want to talk about how Stoicism can be misused, and clear up some of the misconceptions of Stoicism been pr…

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 …

Are you worried about finances? Do you struggle when you have a political conversation with somebody and it becomes heated? Do you worry about failing at life? Well, these are three questions that I'm going to answer today in another Q& A episode. “Too many people spend money they haven’t earned, to buy things they don’t want, to impress people the…

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 (…

Self-made success, individual freedom, pulling yourself up by your bootstraps—these ideas have become the cornerstone of many modern cultures, especially in the West. But is this individualistic mindset really working for us? Today, we’re taking a look at why excessive individualism can be harmful, how it isolates us, and what Stoicism has to say a…

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…

We all suffer heartbreak from time to time. It’s an inevitable part of life with other people. So how can we use Stoicism to help us move past a broken heart? Today, we’re going to discuss how this ancient philosophy has some great tools to mend and move forward. ”There can be no doubt that the desire lovers have for each other is not so very diffe…

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…

As the new year begins, there is always a push to make resolutions and plans. Do you know what you want to accomplish next year? Do you have goals that you want to pursue? How do you plan on accomplishing them? Today I want to talk about some ideas about how you can more successful in achieving the things you want. ”Life is long if you know how to …

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 …

Imagine a bowl, cracked and seemingly useless. Most of us would toss it out. But what if, instead, those cracks were mended with gold, transforming the broken object into something even more beautiful than before? This is the art of kintsugi, a Japanese philosophy that teaches us how to embrace flaws and failures as opportunities for growth and tra…

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…

Have you ever tried to change someone’s mind, only to find them doubling down on their belief instead? Or maybe you’ve felt your own defenses rise when someone challenges your deeply held views? That’s the backfire effect in action—a cognitive bias where contradictory evidence only strengthens someone’s existing beliefs. Today, we’ll explore how St…

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, …

Do you see your emotions as something that get in the way? What if you had no emotions or ignored you emotions, do you think that you would make better choices? In this weeks episode I want to discuss how emotions are guides rather than enemies, and how emotions are the key to help us make better decisions. “Your heart knows the way. Run in that di…

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…

Have you ever wanted to think like Socrates? Well you're in luck! This week's episode is an interview with Donald J. Robertson and we're talking about his new book, How to Think Like Socrates. We talk about the way that Socrates uses questions and critical thinking to overcome our own biases and logical fallacies, and how you can apply those to you…

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…

Do you struggle in getting started with achieving your goals? Do you get overwhelmed and quit before you even start? In this week’s episode I want to talk about how you can change your mindset to help you work through the blocks that are keeping you from living the kind of life you want. “The important thing about a problem is not its solution, but…

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…

This weeks episode is another Q & A episode. I answer a few questions from listener about self gaslighting, romantic relationships, communicating with others, and applying amor fati in my own life. If you have any questions you'd like me to answer in future episodes drop me a note or a comment on social media and maybe I'll feature it in an upcomin…