Send us a text Join Erick Cloward, Stoic author and host of The Stoic Coffee Break Podcast, as he shares how Stoicism transformed his approach to emotions and reactivity. In this 3-minute clip, learn practical Stoic wisdom to stay calm and focused in any situation! 💡 Key Takeaways Feel emotions in proportion to events with Stoic principles. Your pe…

This week I dive into philosophy, life, music, and addiction with my friend Derrick Zaworski. Derrick is a music producer and owner of Road Tripping Records. Derrick and I have been friends for several years and we've always enjoyed deep and interesting conversations, so I thought it would be worthwhile to get one of those conversations on record. …

Do you ever think about your future self? How would your choices in the present change if you took the time to consider those choices would impact future you? Today I want to talk about the power of getting to know the future you. “First say to yourself what you would be; and then do what you have to do.” — Epictetus Send us a text My book Stoicism…

Send us a text In just five minutes, this guided meditation uses a precise 4-2-6 breath and Stoic detachment to separate your calm center from external chaos. By grounding in the body, naming the “turbulence,” and repeating “I am the pilot, not the turbulence,” you’ll instantly regain perspective and control. Designed for use anywhere—desk, car, or…

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…

Send us a text Imagine embracing every twist and turn of life—both pleasant and painful—with open arms. This is the profound Stoic philosophy of amor fati, or "love of fate." Far from passive acceptance, amor fati encourages active enthusiasm toward every event in life. In this comprehensive guide, you'll discover the meaning of amor fati, its Stoi…

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 …

Send us a text Begin each morning with a ten‑minute immersion in Stoic clarity, guided by the words of Marcus Aurelius, Seneca, and Epictetus. This meditation trains you to anchor attention, soften reactivity, and greet every challenge as a chance to practice virtue. You’ll scan body and mind, reframe yesterday’s worries, and pre‑rehearse today’s t…

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…

Send us a text In this clip, renowned Stoicism writer @DonaldRobertson explains why he believes Plato’s Apology is the only book he universally recommends. Donald dives into the profound impact of this short yet powerful text, Socrates’ legendary courtroom defense, and its relevance to Stoic philosophy and modern life. What You’ll Learn in This Cli…

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…

Send us a text This 7.5-minute Stoic morning meditation guides you in the practice of objective representation—seeing events clearly without emotional distortion. You'll be invited to observe a recent experience, separate facts from feelings, and reframe your response with calm and clarity. Inspired by the wisdom of Marcus Aurelius and Epictetus, t…

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…

Send us a text Begin your day with mental clarity and emotional resilience through this 8-minute Stoic meditation. This guided session will help you separate raw events from the judgments you attach to them, giving you the power to observe your thoughts without being controlled by them. Through three simple steps—observing reality, recognizing your…

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…

Send us a text What was Socrates’ relationship with his infamous wife, Xanthippe, really like? Was she an abusive partner, or simply misunderstood within the context of ancient Athenian culture? In this fascinating discussion, I dive deep into Socrates’ domestic life with philosopher and author Donald Robertson. Support the show Resources Stoic Han…

Send us a text In this lesson, renowned Stoicism writer and philosopher Donald Robertson and Jon Brooks reflect on the unique personality of Socrates and his profound love for humanity. Donald compares Socrates to modern-day creative icons, such as Jimi Hendrix, to illustrate his total immersion in philosophy as a way of life. Discover how Socrates…

Send us a text Reading about Stoicism won’t change your life—practicing it will. In this conversation with Donald Robertson, one of the world's leading Stoic authors and cognitive-behavioral therapists, we explore a major misconception: Stoicism isn’t just a philosophy to study—it’s a way of life to train. Support the show Resources Stoic Handbook …

Send us a text What if another person could act as a mirror for your mind? In this thought-provoking conversation with philosopher Donald Robertson we delve into Socrates' timeless insights on wisdom, self-awareness, and the art of questioning. Discover how Socrates used deep dialogue to uncover life’s most fundamental truths and what he meant by a…

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…

Send us a text In this lesson, I speak to Stoicism expert Donald Robertson about how to apply the Socratic method. Discover the timeless wisdom of Socrates and his groundbreaking two-column technique—a simple yet profound method for improving critical thinking, questioning assumptions, and making better decisions. This ancient approach to self-impr…

Send us a text How do you know when to speak up and when to stay silent? When to push forward and when to step back? In this conversation with Donald Robertson, we explore the concept of coping flexibility—the ability to adapt your response based on the situation. Drawing from Stoicism, cognitive behavioral therapy (CBT), and martial arts, we discu…

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…

Send us a text Modern Stoicism often focuses on self-control and resilience, but what if we’ve overlooked its most important lesson? True Stoicism is about strength through compassion. Marcus Aurelius believed that anger is weakness and that true power comes from brotherly love and justice. Yet today, Stoicism is often misrepresented as cold, emoti…

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…

Send us a text In this episode, we explore practical strategies to manage challenging relationships, including high-conflict individuals and those with personality disorders. Drawing from Stoic philosophy and modern psychology, we cover: Why ancient Stoics emphasized handling insults and toxic people. The distinction between caring and caretaking—a…

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…