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Stoic Coffee Break: Daily Summaries Delivered
by Erick Cloward
"Act on your principles, not your moods." A weekly meditation on how Stoic principles can help you be a better human.
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- 3 days ago13 min
Keystone Habits: How One Good Habit Can Change Everything
Habits are a key part of our lives. We have helpful habits that help us accomplish what we set out to do. We also have some that we’d like to get rid of. But what if I told you that sometimes one good habit is all it takes to reorient our lives and make lasting changes? In this week’s episode we’ll discuss the importance of keystone habits and how you can find yours. "All our life, so far as it has definite form, is but a mass of habits." — William James I love to cycle. Ever since I watched the Kona Ironman competition on TV on 2003, and decided that I wanted to be that hardcore, cycling has become become a key part of not just my weekly workout routine, but a core part of my identity. While for some it may sound like torture, a 35 mile ride on a warm Saturday is my idea of an afternoon well spent. But what this one habit brings to my life is far more than just fresh air and great legs. It influences other areas of my life in profound ways. You see, when I started training for triathlons, I was not what a triathlete should look like. I was out of shape. At 195 pounds (about 88 kilograms for you non-Americans) and only 5’7” (170 cm) tall, I was carrying a lot of extra weight. I had bad eating habits, preferring Mt. Dew over water. I could barely run a 5k in under 35 minutes. In high school I could do it in half that time. But once I started down that path, it became the centering principle of my life. I would ride my bike to work, often taking the long way home. I changed my diet to healthier food and smaller portions. When I would go out to eat, I would divide my meals in half, setting aside the second half for home, so I wouldn’t overeat. Because I was working out more, I slept better. And while I only competed in a single short course triathlon before focusing on just cycling, it changed the direction of my life. My gym routine, my diet, my alcohol consumption, and my sleep are all in service to helping me maintain my fitness for the bike. This in turn keeps me healthy, functional, and feeling better mentally. This is what Charles Duhigg, the author of The Power of Habits, calls a “keystone habit”. In short, it’s a core habit that influences other behaviors. It reenforces other habits making them easier to follow. Once you find that habit, it orients the rest of your life around it. The Philosophy A keystone habit isn’t necessarily the most important habit from a moral sense. Cycling doesn’t make me a more virtuous person in itself. A keystone habit is the habit with the highest leverage. It creates an identity shift that makes virtuous choices easier by default, not through willpower. In my case because I consider myself a cyclist, my other choices are filtered through the question: “what would a cyclist do?” In my case: eat less dessert, skip the beer, and get a good nights sleep. A keystone habit doesn’t have to be physical one. It can also be a cognitive one as well. Marcus Aurelius had a keystone habit of writing in his journal. That habit grounded him in way that had an influence on everything else in his life. How he ruled, the books he read, the people he spent time with, how he treated other people. It was a high leverage habit that helped him be the kind of person he wanted to be. Seneca had a habit each night of reflecting on his day. He would take stock of what he did well that day and what he could improve. This simple habit of taking time each day became an anchor for finding his weak spots and resolving to do better tomorrow. Creatures of Habit So why are good habits such an in important part of of lives? Because we are creatures of habits. Literally. Humans develop habits so that we don’t have to think through how to do something every time we do it. Think about if you had to consciously manage each step in getting dressed? If we had to give our full attention to each button or zipper, or each time we had to tie our shoes? It would be tiring. Habits save us time and energy. Think about the first time you learned how to tie your shoes. How much time and effort did that take? It wasn’t easy. But once you got it down, then you could do it without having to really think about it. Bad habits come about the same way. We often pick them up without thinking about them, only to find that they are much harder to put down. I’ve had plenty of friends who picked up smoking because they hung around friends that were smokers. It was easier just to go along to get along. But years later, when trying to quit, they routinely complained about how hard it was, wishing they have never started. Your eating habits were probably shaped by the household you grew up in. As a child you really didn’t have a choice in what food was available in your house. But those choices influenced you and created habits that you probably carried into adulthood. Until w
- 1 weeks ago16 min
The Virtue of Reading | 384
When was the last time that you read a book. A serious book. Something stretched your mind? Something that you had to stop and go back and reread a sentence or paragraph to make sure you understood it? Maybe even learned some new words? New ideas? In this episode, let’s talk about why you should read deeper — not just so you can check another book off your list, but as a tool to help you deal with the complexities of life. “Friends, the school of a philosopher is a hospital. When you leave, you should have suffered, not enjoyed yourself.” — Epictetus The Problem Last year, only 60% of Americans read at least one book. Almost 57% of Americans placed a bet. That's not a statistic I'm making up to be dramatic. It's from a piece in The Atlantic by Rose Horowitch called "The End of Reading Is Here." She's not calling us illiterate. She's calling us something worse, in a way — post-literate. Still surrounded by words. Words everywhere. Just losing the capacity, and the appetite, to sit with the hard ones. The top selling books today are simpler and less complex, with young adult novels taking the lead, even among adults. Libraries are following this trend getting easier to read books for patrons. In 1958 the English translation of Doctor Zhivago was the best selling book. Boris Pastenak wrote in long complex sentences, demanding your attention. Last years top novel? Sunrise on the Reaping, the latest in the Hunger Games series. Nothing wrong with that book, but nobody's calling it a wrestling match. I want to be clear about something before I go further: this isn't me being a snob about it. This isn't "kids these days" or "nobody reads anymore, sad." This is me pointing out something specific — we are choosing, at scale, to stop training the one muscle that everything else in a thinking life depends on. And I don't think that's a coincidence that it's happening at the exact moment we need that muscle most. Difficult reading, as Maryanne Wolf, a cognitive neuroscientist at UCLA points out, strengthens the cognitive abilities of comprehension and synthesis—the ability to read something and integrate it into real life situations. And here's why it matters. When you stop reading hard things, you don't just read less. You lose practice at friction. At hitting a sentence you don't understand and going back over it instead of scrolling past it. At holding two conflicting ideas in your head at once instead of picking a side in the first four words. You start expecting to be handed the conclusion. Told what to feel. And when real life doesn't hand you the conclusion, when it just hands you the mess and expects you to work it out, you're out of practice for the one skill that job requires. Why is Reading Hard? Reading and writing is not something that comes naturally to us as humans. Our brains don’t naturally have a space set aside for processing the written word. This is a skill that we have developed as humans. Writing allowed us to preserve ideas that otherwise would have been handed down orally, and changed in each telling. But in that development we’ve also developed logic, grammar, rationality, mathematics, emotional complexity. In order to put something down on paper, the author has to think through their arguments and clearly articulate what they are actually trying to say, so they can best communicate their ideas to the reader. On the reader’s side, it means that the arguments and ideas don’t disappear as they do when a conversation or video ends. It’s still there on the page, allowing you to go back and dive deeper, consider other possibilities, find rebuttals, and poke holes the flaws you might find. Reading doesn’t just give you information. The act of reading literally changes the way that you think. Reading helps you construct mental models in a way that no other medium can. Reading also places you in the mind of other people. It’s like you experience the world as another person. You read their thoughts and observations. You understand a completely different perspective on that world that you otherwise couldn’t. If you only stick to books that are easy, or ones that speak to your worldview, then you never understand how others experience the world. As we become a more oral and visual world, thanks to social media, we lose something. Social media, while at times can be instructional, is meant to be entertaining and hook your attention, not to deeply educate you. It’s too short for the reader (or watcher) to really engage in the material, to challenge their own thinking. It’s simplified down to soundbites and that’s not a way to educate yourself. If it doesn’t catch your attention, you skim past it looking for something to amuse rather than inform. Vid
- 2 weeks ago1h 5m
Interview with Jon Brooks: Stoicism and Emotions | 383
Jon Brooks is the host of the Stoic Handbook podcast and Substack page. In this episode we talk about the dangers of over-managing your emotions and finding ways to be a good Stoic while not shutting yourself off emotionally. You can find out more about Jon and his work at stoichandbook.co The Build an Unbreakable Mind program for building mental discipline is now open for enrollment!My book Stoicism 101 is available! Order here!Find out more at https://stoic.coffeeWatch episodes on YouTube!Find me on linkedIn, instagram, or threads.Thanks again for listening! Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
- Jun 21, 202615 min
What Does It Actually Take to Be Courageous? | 382
Courage, one of the four cardinal virtues of Stoicism, is what I consider the fuel for virtue, and really for living a good life. But what does courage actually look like? Are we born courageous or it it something we can develop? In today’s episode we’re going to dive into what Stoics taught about courage and how it’s backed up by modern science. What Does It Actually Take to Be Courageous? "Courage is not simply one of the virtues, but the form of every virtue at the testing point." —C.S. Lewis The Problem When I started this podcast, I was scared. Not just nervous. Scared. I was convinced that at any moment, someone was going to figure out that I didn't belong — that I wasn't qualified enough, smart enough, or interesting enough to be talking about Stoic philosophy to strangers on the internet. Imposter syndrome was ever present. Every episode I recorded in those early days, I'd finish it and think, "That’s probably the one where people are going quit listening." But here's what I've come to understand after years of doing this work — that feeling wasn't a warning. It was an invitation. An invitation to do something that takes real courage: to show up honestly, even when you don't feel ready. Today I want to talk about courage. Not the Hollywood version — the battlefield moment, the heroic leap. Real courage. The everyday, grinding, unsexy kind that determines the actual quality of your life. Researcher Brené Brown has spent twenty years studying this. The other day I was listening to a podcast where she was a guest, and they were talking about what it takes to be courageous. What she found in her research cuts against everything we think we know. Courage, she says, isn't a personality trait. It's not something you have or don't have. It's a collection of four learnable skills. And when I dug into her framework for the first time, I kept stopping because the Stoics had already mapped the same territory two thousand years earlier. So that's what we're doing today. Brown's four skill sets of courage, paired with the Stoic philosophy that's been teaching the same lessons since before Rome fell. And I'll tell you where each one showed up in my own life, because if it's worth talking about, it's worth being honest about. Let's get into it. PHILOSOPHY & PRACTICE SKILL SET ONE: Rumbling with Vulnerability Brown's first skill set is what she calls "rumbling with vulnerability." She defines vulnerability as uncertainty, risk, and emotional exposure. And the rumble part matters — it means staying in the discomfort instead of tapping out. Not performing openness. Actually sitting with the hard thing. Most of us don't do this. We armor up. We get busy, get sarcastic, get certain — anything to avoid the exposed feeling of not knowing, of being seen, of possibly being wrong or hurt or rejected. Brown's research shows that without this foundational skill, the other three are impossible. You cannot be courageous while armored. The armor has to come off first, because vulnerability is a prerequisite for courage. You can’t be courageous if something doesn’t scare you. The Stoics called this prosoche — self-examination. The practice of looking honestly at yourself, not to punish yourself, but to see clearly. Socrates felt this was so important that he said, “An unexamined life is not worth living.” He would often practice self-questioning, cross-examining his own thinking about something. Once, while on campaign with the Athenian army, he stood still on a beach for 24 hours, lost in deep thought. The other soldiers, curious about what was going on, gathered around keeping vigil. Then as the sun rose, be woke from his trance-like state, said a prayer to the day, then went on as if nothing had happened. Epictetus pushed his students toward self-examination constantly. And Seneca in his treatise On Anger describes his own nightly practice in first person. He wrote: “When the light has been removed and my wife has fallen silent, aware of this habit that’s now mine, I examine my entire day and go back over what I’ve done and said, hiding nothing from myself, passing nothing by.” And then, crucially, he doesn't spiral into self-condemnation. He says: “For why should I be afraid of any of my mistakes, when I can say: ‘Beware of doing that again, and this time I pardon you.’” That's the practice. See it clearly. Don't hide from it. Just let it go and do better. When I started this podcast, the vulnerability wasn't optional. I was putting my voice, my face, my actual beliefs out into the world with no idea if anyone would care. That exposure, was scary. But the harder vulnerability, the one that took more courage, was admitting to myself that I was afraid. That I felt like a fraud. Because as long as I kept that hidden, even from
- Jun 15, 20261h 8m
Interview with Kelly McGinnis: What it Takes to Really Lead | 381
Kelly McGinnis has a long and storied career working her way up the corporate ladder to CFO and later President of Thermo Fischer, a Fortune 100 company. In this episode we discuss ideas around what it takes to be good leader, company culture, and stepping out on your own. The Build an Unbreakable Mind program for building mental discipline is now open for enrollment!My book Stoicism 101 is available! Order here!Find out more at https://stoic.coffeeWatch episodes on YouTube!Find me on linkedIn, instagram, or threads.Thanks again for listening! Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
- Jun 5, 202610 min
What's the Worst that Could Happen? | 380
“What’s the worst that could happen?” We’ve all heard this before. Usually it’s tongue in cheek just before something really bad does happen. But counterintuitively, it’s actually one of the most powerful questions that we can ask ourselves when we’re stuck in anxiety. So let’s talk about how imagining the worst can you you be your best. “The mind that is anxious about future events is miserable.” — Seneca The Problem In today’s busy world, we all struggle with anxiety. Most people complain about anxiety hampering their daily happiness. And where does this anxiety come from? It’s from worrying about things that we think are going to happen. This is a natural part of being human. The brain is a prediction machine. Think about when you're walking through a crowd, your brain is constantly reading people's trajectories so you don't collide. It does the same thing with the future — always trying to anticipate what's coming next. That capacity kept us alive. If we couldn't imagine bad outcomes, we'd never prepare for them. But most of us have taken that survival tool and turned it into a source of constant stress. What if instead, you could take that same ability and use it to build resilience rather than anxiety? What if considering the worst could help you become your best? The Philosophy Paradoxes In episode 377, I talked about paradoxes — holding competing ideas without rushing to resolve them. It's one of the most powerful skills we can develop, because the moment we choose a side, we close off other possibilities. Seneca puts it plainly: “Ignorance is the cause of fear.” — Seneca The longer we can withhold judgment and hold each idea and try to understand it, the deeper our understanding of it. This is how we gain wisdom, which is not just about knowledge but about being able to see things clearly. Marcus Aurelius captured this idea in his Meditations: “The first rule is to keep an untroubled spirit. The second is to look things in the face and know them for what they are.” — Marcus Aurelius The more clearly we can define what troubles us, the easier it is to turn it to our benefit. Premeditatio Malorum Stoicism is full of paradoxes, but one of the most useful is premeditatio malorum, the “premeditation of evil”. Rather than ignoring what causes our anxiety, we look it in the face. We stop judging it as good or bad and treat it as something that simply is. This is why the Stoics teach that events are neutral. We're the ones passing verdict on them. “It is not events that disturb people, it is their judgements concerning them.” — Epictetus, When we see things as neutral, some of that anxiety loses its grip. The Present Moment Problem Here's the paradox: the Stoics also teach us to be present. To stop worrying about what might happen, and focus on now. In his Letters to Lucilius, Seneca writes: “There are more things, Lucilius, likely to frighten us than there are to crush us; we suffer more often in imagination than in reality.” The anxiety we feel is a direct result of the story we're telling ourselves about the future. We catastrophize. We treat the worst possible outcome as the only one. And what makes it worse — we're doing it to ourselves. The mind has a hard time distinguishing imagination from reality, so the body responds as if the threat is real. Think about a time you were convinced someone was upset with you. You felt the tension. Maybe in your stomach or shoulders. Then you found out you were wrong, and the relief was immediate. Your body was responding to a story, not a fact. That physical distress creates a spiral: thoughts create story, story creates sensation, sensation triggers the fight-or-flight response, which narrows your thinking to the very thing you're afraid of. That's why getting someone to breathe slows the spiral. Calm the body first, then the mind follows. Avoidance Makes It Worse When we try not to think of something, we give it more power. It’s the pink elephant problem. Try not to think about about a pink elephant and you will think about one. The brain has to imagine a concept before it can dismiss it. It can’t operate in a void, and suppression takes energy. So the fear stalks you. You scroll your phone. You have a drink. You eat things you shouldn't. Anything to avoid sitting with it. But Seneca reminds us: “Everyone faces up more bravely to a thing for which he has long prepared himself, sufferings, even, being withstood if they have been trained for in advance. Those who are unprepared, on the other hand, are panic-stricken by the most insignifican
- May 28, 202610 min
Why Searching for Meaning Is Keeping You Stuck | 379
Marcus Aurelius was the most powerful man on Earth. He had every external condition for a meaningful life — wealth, status, purpose handed to him by birth. And yet, his private journals are full of reminders he had to write to himself just to keep going. Which tells you something important: meaning isn't a thing you find. It's a thing you build. The Problem Do you live a meaningful life? Not "are you successful" or "are you productive" or "are you optimizing your mornings”, but does your life actually feel like it means something? Here's what I've come to believe: Don't try to find the meaning of your life. Do things that bring meaning into your life. It’s a subtle shift, but it leads to a completely different life. Finding the meaning of your life is, honestly, an unanswerable question. Philosophers and thinkers and spiritual teaches have been wrestling with it for millennia. You could spend your whole life searching and never arrive. It's the ultimate question. But doing things that add meaning to your life? That is under your control. That's where you have agency. That's where you can actually act. So why is "what is the meaning of my life?" the wrong question? Because searching for meaning looks outward. You're scanning the horizon for something to reveal itself. A bolt out of the blue, a mountain-top moment, a sudden clarity that finally tells you what you're here for. And while you're waiting for that, you're sitting on the sidelines. Ready to start living once you figure out what your life is for. Which may be never. Seneca cuts right to it. In his Letters to Lucilius he writes: "If a man knows not to which port he sails, no wind is favorable." It sounds like saying figure out the destination before you set sail. But I’d like to broaden the interpretation. I think he's saying: pick a direction. A direction that matters to you. Start sailing. Because a ship that's moving can be steered. A ship sitting in the harbor waiting for perfect conditions goes nowhere. You don't need the full map. You just need to start. Why It Matters So why does meaning matter so much? Meaning is what makes the suffering in life worth it. When our lives feel meaningless, we feel hopeless, like we're going through the motions with no point to any of it. This is why people who are deeply dissatisfied with their lives can spiral so quickly into depression. They feel like a cog in a machine. A robot. Present but not alive. This is also why money and status are such terrible proxies for a meaningful life. You can hit every external marker — the salary, the promotion, the recognition — and still feel completely empty. We attach meaning to outcomes, when really it lives in the effort. If you're working on something that genuinely matters to you, you do it because it fills your soul, even when it doesn't fill your wallet. Viktor Frankl understood this at a depth most of us will never have to. A psychologist and Holocaust survivor, he observed in the camps that the prisoners who had a stronger why, a deeper sense of meaning, were more likely to survive. They were less likely to lose hope. More likely to help those around them. They knew the circumstances were devastating. But they didn't let those circumstances determine who they were. They made meaning from what little they had: a sunset, a memory, a connection, a small act of kindness. Frankl wrote: "Everything can be taken from a man but one thing: the last of the human freedoms — to choose one's attitude in any given set of circumstances, to choose one's own way." That's not naive optimism. That's radical agency. That's Stoicism in practice. He also quoted Nietzsche directly: "He who has a why to live can bear almost any how." The suffering doesn't disappear. But it becomes bearable when it's in service of something that matters to you. Meaning vs. Purpose Before we get into what you can actually do, I want to draw a distinction I think is important: the difference between meaning and purpose. We use these words interchangeably, but they're not the same thing. Purpose is the what of your life. Meaning is the why. Purpose is concrete and actionable. If you're a teacher, your purpose might be to prepare young people to live well. That’s clear and definable. Meaning is what you derive from that purpose — the quiet satisfaction when a student finally gets something, or when someone reaches out years later to say something you said changed their trajectory. You can't schedule that feeling. It arises from the doing. Marcus Aurelius, in Meditations, wrote: "Waste no more time arguing about what a good man should be. Be one."</p
- May 19, 202616 min
Collaborating with Reality: The Stoic Art of Being Present | 378
Far too often we’re never really in the moment. Maybe we’re stuck ruminating in the past over what we wished would have happened, or projecting out into the future our hope of what will happen. Maybe we distract ourselves with our phones, with entertainment, or alcohol or drugs. Anything that can relieve boredom or the discomfort of our present reality. But what if you leaned into that boredom? What if embracing discomfort is the key to really experiencing your life? In this episode I want to about the importance of being present in your own life by working with reality, rather than against it. “Caretake this moment. Immerse yourself in its particulars. Respond to this person, this challenge, this deed. Quit evasions. Stop giving yourself needless trouble. It is time to really live; to fully inhabit the situation you happen to be in now.” — Epictetus Sitting With Discomfort The other day I was listening to a conversation on the Ezra Klein Show. He was interviewing Pema Chödrön, a Buddhist nun who has spent decades writing and teaching about how to actually live with uncertainty, discomfort, and pain. If you haven't come across her work, I'd encourage you to look her up. The conversation moved through a lot of territory, but one theme kept surfacing, and it's been sitting with me ever since. Sitting with discomfort. Both emotion and physical discomfort. Not trying to change them. Not trying to fix them or think your way out of them. Just being aware of them, and letting them be part of your experience. Now I know that can sound passive, like you're supposed to suffer quietly and call it wisdom. But that's not what they were talking about. What they were getting at is something more precise: when we resist how we're feeling, we don't reduce the pain. We add to it. We take whatever discomfort is already present and we pile on — the worry, the frustration that we feel this way at all, the disappointment that reality isn't matching what we wanted. We make it worse. Pema talked about how one of here mentors used a phrase that I think is one of the best framings I've heard: collaborating with reality. Collaborating with reality. Not fighting it. Not wishing it were different. Not white-knuckling your way through it while secretly hoping it changes. Collaborating with it. And the moment I heard that, I thought — that's exactly what the Stoics meant when they said we should live according to nature. Same insight, two and a half thousand years apart, from completely different traditions. But here's the dimension I want to explore today, because I think it goes deeper than most conversations about presence and acceptance actually go. We don't just resist painful emotions. We disconnect from them entirely. We go numb to them. And we do the same thing with physical pain. We get so caught up in the noise of our daily lives that we stop receiving the signals our own bodies and our own hearts are sending us, even when those signals are urgent. I know this firsthand. And I’ll tell you a story about that in a minute. The Philosophy The Stoics had a concept called the hegemonikon — the ruling faculty. It's the part of us that perceives, judges, and assigns meaning to everything that happens to us. In an ideal state, this faculty governs us well. It sees clearly. It distinguishes between what's in our control and what isn't. It responds to reality rather than reacting to it. But here's what Marcus Aurelius kept noticing about himself and what he wrote about in repeatedly in his Meditations: “Don’t let your imagination be crushed by life as a whole. Don’t try to picture everything bad that could possibly happen. Stick with the situation at hand, and ask, “Why is this so unbearable? Why can’t I endure it?” You’ll be embarrassed to answer. Then remind yourself that past and future have no power over you. Only the present—and even that can be minimized.” — Marcus Aurelius The mind wanders and the ruling faculty, left undisciplined, reaches backward into regret and forward into anxiety. It is almost never simply in the present. What I love about Marcus is that he wasn't writing from a place of mastery. He was writing to himself, often about his own failures. He kept having to drag himself back to the present. Epictetus put it even more plainly: “Some things are up to us. Some things are not.” When we expend energy on the things that are not up to us, including resisting what is simply happening, we suffer. Not because those things are bad, but because we are fighting a battle we cannot win. This is what collaborating with reality means in Stoic terms. It's not apathy. It's not indifference. It's an active choice to stop expending energy on resistance to
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"Act on your principles, not your moods." A weekly meditation on how Stoic principles can help you be a better human.
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