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Stoic Coffee Break

Erick Cloward
Stoic Coffee Break
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382 episodes

  • Stoic Coffee Break

    Interview with Kelly McGinnis: What it Takes to Really Lead | 381

    15/06/2026 | 1h 8 mins.
    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.coffee

    Watch 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.
  • Stoic Coffee Break

    What's the Worst that Could Happen? | 380

    05/06/2026 | 10 mins.
    “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 insignificant happenings.” — Seneca

    The courage to face it head-on is the path through.

    Outcomes

    One more thing worth naming: when we fixate on outcomes, we lose agency. Outcomes aren't under our control. Actions are. That's why the focus has to shift to what you can actually do — not what might happen.

    But here’s another part of the paradox. We do have to consider what might happen, consider other possible outcomes. Even ones that we’re not focused on at the moment. As Seneca writes:

    “What is quite unlooked for is more crushing in its effect, and unexpectedness adds to the weight of a disaster. The fact that it was unforeseen has never failed to intensify a person's grief. This is a reason for ensuring that nothing ever takes us by surprise. We should project our thoughts ahead of us at every turn and have in mind every possible eventuality instead of only the usual course of events.” —Seneca

    This isn’t about running a catastrophizing session. It’s considering as many possible bad outcomes as you can so that you aren’t caught by surprise. You don’t have to do them all at one time, but by taking on the things that scare you, you’re following Seneca’s advice:

    “So I look for the best and am prepared for the opposite.” —Seneca

    The Practice

    So how do you actually do this — and what makes it different from just ruminating?

    Two things. First, you do this in a safe space — not in the heat of the moment, but sitting quietly with time to think. Second, you approach the problem with objectivity. And objectivity isn't cold. Think about the friends you trust most — they're the ones who tell you the truth, not what you want to hear. This practice is you doing that for yourself.

    Seneca explains this clearly:

    “This is why we need to envisage every possibility and to strengthen the spirit to deal with the things which may conceivably come about. Rehearse them in your mind: exile, torture, war, shipwreck. Misfortune may snatch you away from your country… If we do not want to be overwhelmed and struck numb by rare events as if they were unprecedented ones; fortune needs envisaging in a thoroughly comprehensive way.” — Seneca

    Now, it’s important that you write it down. Don't do this in your head. Getting it on paper creates distance. You see it more clearly. You have to actually articulate the thing.

    This practice that I’m going to share with you is one from my course, Build an Unbreakable Mind. If you find this useful and want to learn more useful practices, make sure to check it out on my website at stoic.coffee/unbreakable

    Step 1 — Write down the the story you're telling yourself. It can be freeform, or you can ask yourself:

    What outcome am I afraid of?

    What do I think happens if that outcome occurs?

    What doubts do I have about myself?

    What assumptions am I making?

    Step 2 — The facts.

    These are things that could be proven in a court of law:

    What are the actual roadblocks?

    What's outside my control?

    What skills do I have? What am I lacking?

    No opinions. Only what could be proven.

    Step 3 — The emotions:

    Write down everything you're feeling. Angry, sad, scared, nervous. All of it. Get it out.

    Then take a break. Step away. Come back later with fresh eyes.

    Step 4 — What you can actually do:

    How will you handle the roadblocks?

    What could you learn to close the gaps?

    If the worst actually happened — what would you do?

    What's under your control right now?

    Where can you take action today?

    This is how you rewrite the story. You use your rationality to see more clearly, and shift your perspective toward something useful.

    Conclusion

    Anxiety about the future is part of being human. You're not going to think your way out of having it. But you can stop fighting it and start using it.

    Premeditatio malorum is leaning into the fear. It's having the courage to ask: what am I actually afraid of? It's sitting with the hard thing — clearly, not catastrophically — and dismantling the doom loop before it dismantles you.

    So the next time you catch yourself trying not to worry about something — stop resisting. Welcome it in. Look it in the face.

    And ask: “What's the worst that could happen?”

    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.coffee

    Watch 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.
  • Stoic Coffee Break

    Why Searching for Meaning Is Keeping You Stuck | 379

    28/05/2026 | 10 mins.
    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."

    He wasn't meditating on the cosmic meaning of his reign. He was building his character, one decision at a time. The meaning came from the practice, from doing the work with integrity, even when nobody was watching. Especially when nobody was watching.

    The Practice

    So what can you actually do? Two things.

    First: actively do things you find meaningful.

    I think we spend too much of our lives optimizing for productivity. We stop doing things we love because they're not monetizable, or they don't look good on a resume. The way we evaluate our time has become almost entirely economic.

    Flipping that script means asking not "is this productive?" but "does this matter to me?" That might be meditating, hiking, making art, playing music, building something with your hands — things that feed your soul even if they don't feed your bank account.

    And creativity doesn't have to mean art. Building a fence is creation. Tending a garden is creation. Volunteering your time, helping people who need it, furthering a cause you believe in — those are acts of meaning because you're participating in something larger than yourself.

    One of the most reliable ways to bring meaning into your life is simply to help other people. Service is a core component of a good life — and clinical research actually backs this up. Helping others is one of the most consistent mood elevators we know of.

    When I was in college, my family had a Thanksgiving tradition. Instead of cooking a big feast at home, we'd volunteer at the Greek Orthodox church in downtown Salt Lake City — feeding people who were homeless or struggling. We'd spend the day cooking and serving. Honestly? It was one of the most fulfilling things I've ever done. That memory still carries weight decades later.

    Second: shift your perspective and find meaning in what you're already doing.

    This is about rewriting your own story — not gaslighting yourself, but genuinely looking at what you're doing through a different lens.

    Raising kids isn't always fun. At times it's brutal. But ask most parents whether it gave their life meaning, and they'll say yes without hesitating. The hard parts and the meaningful parts aren't separate — they're inseparable.

    The same can apply to work. If you have a job you don't love, can you find aspects you do? Can you reframe it as service to others? As developing skills that will serve you later? Maybe it's simply the price you pay to support yourself so you can do the things that actually matter outside of work.

    Now — I want to be clear: this isn't about talking yourself into tolerating a toxic situation. Some environments are genuinely harmful. Some jobs are soul-crushing. Wisdom knows the difference between genuine reframing and self-deception. But for the ordinary friction of ordinary life, the Stoics would tell you the meaning isn't waiting for you somewhere else. It's available right here, if you're willing to look.

    Epictetus, who was born a slave and had nearly nothing in terms of external freedom, put it plainly in the Enchiridion: "Make the best use of what is in your power, and take the rest as it happens."

    You don't control everything that happens to you. You do control what you make of it.

    Conclusion

    I want to get personal for a minute, because this isn't abstract for me right now.

    A few years ago, my kids grew up and moved out, a long-term relationship ended, and I got laid off, all around the same time. That's a lot of structure collapsing at once. I felt rudderless. Like I didn't have much meaning in my life anymore.

    When I was supporting my kids, even a job I didn't love felt meaningful because I was providing for them. That gave it weight. But with a blank slate and no one depending on me, all the constraints that had organized my life were gone. It turns out, constraints aren't only limitations. They're also anchors.

    So for the past few years, I've been making the same mistake over and over: treating meaning like something out there to be discovered. Like if I could just find the right framework, the right direction, the right answer, it would reveal itself.

    I was going about it completely backwards.

    Meaning isn't something you find. It's something you build from the small, concrete things you choose to do each day. I find meaning in creating this podcast. From the emails and comments that remind me these episodes have actually helped someone. I find it in the creative work, the conversations, the things I choose to put my energy into.

    The overarching meaning of my life? I still don't have a neat answer for that. But I'm learning I don't need one. I just need to keep doing things that matter and trust that the meaning takes care of itself.

    Maybe that's enough for now. I think it might be enough for all of us.

    So I want you to take some time this next week and think about: What's one small thing you do that gives your life meaning — even if it's not productive?

    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.coffee

    Watch 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.
  • Stoic Coffee Break

    Collaborating with Reality: The Stoic Art of Being Present | 378

    19/05/2026 | 16 mins.
    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 what is and redirect that energy toward how you actually respond.

    The Stoics weren't saying don't feel. That's the misreading that turns this philosophy into emotional flatness. They were saying: feel what's actually happening. Not what you've constructed around it. Not the story on top of it. The thing itself.

    The acceptance of what is leads to a richer, fuller experience. Life isn’t meant to be about comfort. It’s meant to be experienced. All of it. If we ignore or avoid the painful things, we’re ignoring reality and cutting off our lived experience.

    Which raises the harder question. If this is clearly the wiser path — and the Stoics knew it, Buddhist teachers know it, most of us sense it intuitively — why is it so hard? Why do we keep disconnecting?

    I think the answer has to do with something we don't talk about enough.

    The Ego Problem

    During the conversation between Ezra and Pema, they mentioned the work of Jon Cabot Zinn who works with people with chronic pain and using meditation to deal with it. And what’s interesting is that the approach is not to ignore the pain, but to become even more aware of it. By become aware of it and not resisting it, they found it actually reduces pain. It changes the relationship with it because they learned to accept it and live with it and no longer resist.

    And that part of the discussion reminded me of an experience I had with pain.

    When I was around 30, I started having numbness in my feet. I went to a podiatrist to figure out what was going on, and he told me it was most likely a back issue, because it was bilateral, on both feet, which pointed to the spine rather than to the feet themselves.

    He referred me to a physical therapist.

    In our first session, my physical therapist asked me if I had any pain in my lower back. I thought about it and said, “a little, maybe, but nothing significant”. He asked what I did for work. I told him I was a software engineer. He smiled and said that was one of the worst jobs for back health. Hours of sitting, forward-bent posture, the whole thing. And he said: start paying attention to your lower back at work. Notice what you're actually feeling.

    The next day, just before lunch, I remembered what he said. So I stopped and I actually checked in with my body. Really checked in.

    I couldn't believe how much pain I was in.

    It wasn't mild. It was significant. And it had been there for I don't know how long. Long enough to have stopped registering it. I had been living in real pain, every day, and I had gotten so good at tuning it out that I genuinely didn't know it was there until someone told me to stop and look.

    That stopped me. Because if I could be that disconnected from something as concrete and physical as pain, something my own nervous system was actively generating, what else was I not receiving? What other pain was I tuning out?

    Here's what I think was happening, and why I think it matters.

    A psychologist named Dan McAdams developed what's called narrative identity theory. The idea is that we construct who we are through story. We take the raw material of our lives and we edit it into a coherent autobiography: themes, patterns, a sense of where we've been and where we're going. We create a story about ourselves and out lives.

    That's not a flaw. It's actually how human identity works. But the story requires past and future to function. You can't have a narrative about the present moment. The present is just happening. It has no arc yet.

    Which means when we're deep in the story of our lives — the job, the responsibilities, the mental to-do list — we stop receiving what's actually occurring. We're so immersed in the narration that the experience itself gets crowded out.

    Daniel Kahneman named this distinction precisely. He separated the experiencing self, what's actually happening to you right now, from the narrating self — the one constructing and remembering the story of what happened.

    And here's the uncomfortable part: the narrating self is dominant. It's the one we primarily identify with. It's the one that decides how we feel about our lives. Not what we're actually experiencing, but the story we tell ourselves about it.

    So we're almost never fully in our experience. We're in our interpretation of it.

    My lower back was sending a clear signal. My narrating self was too busy running its story to receive it. The signal was there the whole time. I just wasn't home.

    And I think we do the exact same thing with emotional pain.

    When something hurts emotionally, like grief, loneliness, fear, or shame, the narrating self kicks in immediately. It starts explaining. It starts planning. It starts building a story that makes the feeling manageable, or it builds a story that justifies avoiding the feeling altogether. We get busy. We fill the silence. We find reasons not to sit with what's actually there.

    We numb out. Just like I numbed out to my back.

    There's neuroscience behind this. Researchers have identified what's called the Default Mode Network which is a set of brain regions that activate when you're not focused on a task. When your mind is wandering. And what does it do? It generates self-referential thinking. It replays social situations. It plans. It constructs your sense of self.

    It's the neural substrate of the narrating self. And it's most active when you're supposedly doing nothing, which is why doing nothing feels so loud. The moment you stop feeding the network with tasks and distractions, it cranks up the internal noise.

    This is what boredom actually is. It's not an absence of stimulation. It's what happens when the ego loses its feed. When there's no story to maintain, no distraction to process — you're just there. And that feels threatening. Not because something bad is happening, but because the part of you that needs to be someone has nothing to work with.

    Research on presence and meditation shows that sustained attention on the present moment measurably quiets the Default Mode Network. Presence isn't passive. It's neurologically active. You're actively suppressing the story-making machine.

    And that is where emotional courage comes in.

    Because sitting with physical pain, really sitting with it, like my PT was asking me to do, requires a kind of courage. You have to be willing to feel what's actually there rather than staying numb. And sitting with emotional pain requires exactly the same thing. You have to be willing to stop narrating around it, stop explaining it away, and just be with it.

    That's not suppression. Suppression is forcing the feeling down. This is the opposite. This is opening to what's actually present, without adding a story on top of it.

    That is the courageous act.

    The Practice

    So how do you actually practice this?

    I want to offer a metaphor that I've been sitting with, because I think it captures something important.

    Think about what happens when you're deep in a video game. A good one. One you're genuinely invested in.

    You don't argue with the rules. You don't wish the level were designed differently. You take the game as it is, and you engage with what's in front of you. Each challenge is just the next thing. You're not catastrophizing it or resenting it. You're playing it.

    And here's what I really want to point at: when you're fully in it, you forget yourself. You're not monitoring your performance or worrying about what others think. The narrating self goes quiet. There's just the experience. Psychologists call this flow, and it's not accidental that people describe flow states as some of the most satisfying experiences they have. Because in those moments, the gap between the experiencing self and the narrating self collapses. You're just there.

    Life isn't a video game. I know the metaphor has limits. The stakes are real. The consequences follow you. You choose your own direction.

    But the principle holds: whatever level you're on right now, whatever challenge is in front of you, the question is whether you're going to stand outside it, arguing with the design, or whether you're going to play it, fully and presently.

    Collaborating with reality doesn't mean you're happy about everything that happens. It means you stop expending energy on the fight with what is, and start putting that energy into how you actually respond.

    Epictetus reminds us of this idea:

    “If we try to adapt our mind to the regular sequence of changes and accept the inevitable with good grace, our life will proceed quite smoothly and harmoniously.”

    — Epictetus

    That's where your power is. Being in the moment. Experiencing your life rather than narrating it.

    Sot there’s two things I'd invite you to try this week.

    The first: at some point during the day, stop and actually check in with your body. Like my physical therapist asked me to do. Not a quick scan, but a real one. Start at your feet and move upward. Notice what's there. You might be surprised what you've been ignoring.

    And then ask yourself: am I doing the same thing emotionally? Is there something I've been numbing out to, narrating around, staying too busy to actually feel?

    The second: find one moment today where you’re faced with boredom, frustration, or discomfort you can't immediately fix, and instead of reaching for the phone or filling the space, just stay with it for sixty seconds. Don't analyze it. Don't build a story around it. Let it be what it is.

    That's the practice. Small, repeatable, and harder than it sounds.

    Marcus Aurelius kept dragging himself back to the present. Not because he arrived. Because returning was the work.

    Learning to be present and in the moment is challenging because we don’t like to sit with discomfort and because we have so many ways to avoid it. But by avoiding it, we’re cutting ourselves off from experiencing our lives.

    The signal is there.

    The question is whether you're home to receive it.

    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.coffee

    Watch episodes on YouTube!

    Find me on linkedIn, instagram, or threads.

    Thanks again for listening!

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  • Stoic Coffee Break

    The Power of Paradox: The Stoic Art of Holding Two Truths at Once | 377

    06/05/2026 | 19 mins.
    Can two things be true at the same time? Can you hold two opposing ideas at the same time? Today I want to talk about how learning be be comfortable with opposites can widen your thinking and help you see reality a little more clearly.

    "The opposite of a correct statement is a false statement. But the opposite of a profound truth may well be another profound truth." — Niels Bohr

    There's a moment most of us know but rarely name. You're sitting with something — a relationship, a decision, a feeling — and two things are true at the same time. You love them, and you're furious with them. You're proud of the life you built, and you wonder if you built the wrong one. You're doing your best, and your best isn't good enough yet.

    And there's a pull. A real, almost physical pull, to flatten it. To pick one. To call your partner the villain, or to swallow your anger and pretend you're fine. To lock in a judgment and walk away from the discomfort.

    That pull is the enemy of clear thinking. And today we're going to talk about how to resist it.

    Today's episode is about paradox — about holding two opposing things in your mind at the same time without collapsing them into a single comfortable lie. It's one of the hardest skills a person can build, and one of the most important. Let's get into it.

    The Premature Collapse

    Here's the problem. The human mind hates unresolved tension. It feels like an itch. It feels like something is wrong and needs to be fixed. And so when life hands us a situation where two opposing things are both true, we don't sit with it. We collapse it. We pick a side, fast, before the situation has earned a verdict.

    I want to give that move a name today, because naming it is half the battle. I'm calling it premature collapse. The moment you flatten a complicated truth into a simple story so you can stop feeling the discomfort of holding both. It's the lazy move. It feels like clarity, but it's actually relief masquerading as clarity.

    Let me give you the tell. The tell is when AND turns into BUT.

    ”I love them, but I'm angry.” That sentence cancels one of the two feelings. The ”but” tells your brain, and the person you're talking to, that the anger is the real thing and the love is a footnote.

    Now try this: ”I love them, and I'm angry.” Same words. Different universe. Now both are true. Now neither cancels the other. Now you're telling yourself the truth instead of editing it down to something easier to carry.

    That tiny grammatical move, replacing ”but” with ”and”, is one of the most powerful psychological shifts I know. We'll come back to it.

    I recently celebrated my birthday. For me, birthdays aren’t a huge deal. But this one was a little different. I’m now the same age that my father was when he died. And it got me thinking about our relationship, even though he’s been dead for almost 30 years.

    For those of you who have listened to my podcast for a while, you know that my relationship with my dad was not great. He was periodically violent and angry which made for a traumatic upbringing that took me a long time to resolve.

    But the hardest part was the paradox of my father. He was smart, funny, and pretty supportive. He worked hard to make sure that we had everything we needed. He taught me how to ride a bike. He came to my plays and concerts. He loved science and music. He was curious about the world. There were so many things that I loved about him, and yet, he was caused a lot of fear, stress, and anxiety in our home.

    After he died I was still angry with him. It took a lot of time and energy to heal those wounds. Part of me felt like I should hate him, but as I became a father, and went through my own struggles, I began to soften. I realized that I could hold that tension—I could still love him, and not approve of what he did. I could forgive him, which to be honest was more for myself since he was gone, and not discount the damage that was done.

    Holding that tension was not easy, but it opened up my view of seeing that he was was also hurt and damaged. That he had never healed from the trauma from his childhood. It made me more empathic and more vigilant about not passing that type of trauma onto my own kids.

    I could have stayed with the anger, but it wouldn’t have been helpful or productive. It would have made me bitter.

    So why do we do it? Why do rush to choose a side?

    A few reasons.

    It's metabolically cheaper. Holding two opposing ideas costs the brain real energy, and picking a side is an energy savings.

    It feels like decisiveness, which our culture rewards.

    It signals tribal belonging. Once you pick a side, your people know you.

    And it relieves the ache. ”He hurt me AND I love him” is harder to sit with than ”he's a villain” or ”I forgive him.” Either resolution is easier than the truth.

    But the cost is enormous. You distort reality. You build an identity on a half-truth. And every future situation that resembles this one gets filtered through the wrong story.

    So what do we do instead?

    Act 2 — Paradoxes Aren't Problems to Solve

    The first reframe is this: a paradox is not a problem to be solved. It's a tension to be held.

    Most of us were trained to think the opposite. Western logic, going back to Aristotles assumes that something is either true or false. Either/or. Pick one. Other traditions such as Taoism and Zen Buddhism, handle paradox more naturally, but most of us didn't grow up with this idea. We grew up in a culture that treats unresolved tension as a failure of thinking.

    It isn't. Sometimes the tension is the truth.

    F. Scott Fitzgerald wrote:

    ”The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function.” — F. Scott Fitzgerald

    Notice what he says. Not just hold them. Hold them and still function. That's the skill. Not paralysis. Not retreat into mush. To actively live inside the tension.

    The Stoics built this into their entire operating system. Look at the dichotomy of control. Care fully about outcomes, pursue them, and work for them, and remain unattached to whether they happen. That's a paradox. Most people resolve it the wrong way and call it Stoicism. They go cold and stop caring and that's not what the Stoics taught. The Stoics taught full effort, full investment, and fully releasing expectations. Both at once. That’s the brave version.

    Or this one: you are cosmically insignificant, a speck on a speck floating through indifferent space. And your virtue, in this moment, matters infinitely. Both. At once. Try to keep just one and you get nihilism on one side or grandiosity on the other.

    Marcus Aurelius is the working example of a man who lived inside paradox without trying to escape it. He was the most powerful person on Earth. As emperor of Rome he was the absolute authority of the known world, and he reminded himself daily that he was already as good as dead.

    He wrote:

    ”You could leave life right now. Let that determine what you do and say and think.” — Marcus Aurelius

    That isn't nihilism, rather that's the engine of his ethics. The brevity of life is what made living virtuously urgent.

    He held these paradoxes everywhere. He was a philosopher AND a soldier running a brutal frontier war that lasted most of his reign. He believed in the rational order of the cosmos AND he wrote constantly about how venal and exhausting the people around him were. He'd open the day with gratitude — ”think of what a precious privilege it is to be alive, to breathe, to think, to love” — and on the next page, basically: people are going to be insufferable today, accept it and keep moving.

    Meditations doesn't exist if Marcus picks a side. If he leans full optimist, the book gets saccharine. If he leans full cynic, it gets cold and small. The greatness of that book and the reason we still read it eighteen hundred years later, is that he refuses to resolve the tension. He holds both, in private, every night, for years.

    That's not a flaw in his thinking. That is his thinking.

    Or look at Viktor Frankl, who survived the camps and gave us Man's Search for Meaning. The paradox at the heart of his work is recursive — it contains itself. Suffering produces meaning, AND meaning redeems suffering. Try to keep just one half and the whole structure collapses. Suffering without meaning is despair. Meaning without the willingness to suffer for it is shallow. You need both. The suffering clarifies what matters. The meaning makes the suffering worth it. Each one feeds the other.

    If Frankl had collapsed that paradox, the book wouldn't exist either. He'd have written a book about how suffering destroys us, or a book about how positive thinking saves us. Neither one would be true.

    Heraclitus saw this twenty-five hundred years ago:

    ”The way up and the way down are one and the same.”  — Heraclitus

    Carl Jung taught that holding the tension of opposites is the actual work of becoming a whole person, and that collapsing the tension is where neurosis lives.

    Different traditions, different centuries, and yet, the same insight. The wise person isn't the one who has all the answers. It's the one who can stay in the question without panicking.

    And here's where this connects to everything else we talk about on this show. The suppression of emotions that I push back against every week, like pretending you're fine when you're not, or acting tough instead of feeling things is premature collapse. It’s just applied to feelings instead of ideas.

    When there’s a big change in your life you can feel two things at once. You can grieve about a loss in your life, AND be excited for something new. You can feel sad about the ending of a relationship AND hopeful about what comes next. You can feel excited about new job AND still feel like an imposter.

    Holding paradox IS emotional courage. Same muscle. Whether you're holding two feelings, two truths about a person, or two truths about your own life, the practice is the same. Don't collapse. Stay with it.

    How to Hold the Tension

    How do we actually get better at this? I'm going to give you three tools, and I'm going to spend the most time on the first one because I think it's the most powerful and the most teachable.

    1. Steel-man the side you reject.

    This is the practice of building the strongest possible version of the view you disagree with. Not the cartoon version. Not the version that's easy to knock down. The version its smartest defenders would actually make.

    This is the opposite of straw-manning, which is what most of us do most of the time. Straw-manning is taking the weakest version of the other side, lighting it on fire, and feeling like you won. It feels like thinking but it isn't.

    Steel-manning is the real workout.

    John Stuart Mill said it better than I ever could. He wrote this in 1859 in his book On Liberty, and it's somehow more relevant now than it was then. Listen to this carefully:

    ”He who knows only his own side of the case, knows little of that. His reasons may be good, and no one may have been able to refute them. But if he is equally unable to refute the reasons on the opposite side — if he does not so much as know what they are — he has no ground for preferring either opinion.” — John Stuart Mill

    Read that again. If you can't argue the other side, you don't actually know your own side. You just inherited it. Your conviction isn't conviction. It’s habit wearing conviction's clothes.

    And Mill goes further. He says it's not enough to hear the opposing view from people on your own team, presented the way they present it, with their refutations baked in. You have to hear it from people who actually believe it. People who defend it in earnest. People doing their very best for it. You have to know it, in his words, ”in its most plausible and persuasive form.”

    That's the work. And most of us aren't doing it. Most of us are arguing against versions of the other side that no thoughtful person actually holds, and calling that thinking.

    So here's the exercise. This week, pick one belief you hold strongly. It doesn't have to be political. It can be about your relationship such as: my partner is the one who needs to change. It can be about your career: I should leave this job. It can be about yourself: I'm not the kind of person who can do that.

    Pick one. Spend ten minutes writing the strongest possible case against your position. No rebuttal. No ”but here's why I'm still right.” Just build the opposing case, in good faith, the way someone who actually believes it would build it.

    Two things will happen. Either you'll find your position got sharper, because now you understand what it's actually responding to and you can defend it on real ground. Or you'll find your position got more humble, because the other side has more weight than you wanted to admit. Both are wins. Both are how you become harder to fool, including by yourself.

    And let me point out something important: This isn't fence-sitting or moral relativism. This isn't the lazy ”both sides have a point” cop-out. You can steel-man a view and still reject it. Mill did. Marcus did. The point isn't to abandon your conclusions. The point is to earn them. To know that your position is yours because you tested it against its strongest opposition and it held — not because you've never seriously examined it.

    That's the difference between a conviction and an inheritance. Most of us have inheritances. Steel-manning is how you turn them into convictions.

    2. AND, not BUT.

    I told you we'd come back to this. The grammatical fix is small, but the psychological outcome is enormous.

    Listen for the word ”but” in your own speech this week. ”I love my work, but I'm exhausted.” Replace it with ”and.” ”I love my work, and I'm exhausted.” Now both are true. Now you can think clearly about what to do, because you’re seeing the situation more clearly.

    Some other places you might hear it include:

    ”I’m proud of my kids, but I'm worried about them.”

    ”I want to be there for my partner, but I need time alone.”

    ”I’m doing my best, but I can do better.”

    ”I forgive them, but I don't trust them yet.”

    Try it for a day. You'll be amazed how often you catch yourself canceling out half of what's true.

    3. Map the polarity.

    Here's a journal prompt: Pick a situation in your life that's been bothering you. At the top of the page, write: ”Two things that are both true about this.” Then write them. Don't reconcile them. Don't pick a winner. Just hold them on the page where you can see them.

    Then add a layer.

    There's a thinker named Barry Johnson who wrote about something called polarities. His idea is that a lot of the tensions in our lives aren't problems to be solved — they're polarities to be managed. Work and rest. Independence and connection. Stability and change. Discipline and spontaneity. Freedom and commitment.

    Try to ”solve” any of those by picking one pole and you destroy something essential. Rest with no work is rot. Work with no rest is burnout. Connection with no independence is enmeshment. Independence with no connection is loneliness. The skill isn't picking. It's moving fluidly between the two as the moment requires.

    So extend the journal prompt. Identify a polarity in your life. Write down what each pole gives you when you honor it, and what each pole costs you when you pull too hard to one side. You'll see the shape of your own imbalance pretty quickly. The goal isn't a resolution. The goal is a map.

    Conclusion

    Here's where I want to leave you.

    The brave move isn't picking a side. The brave move is refusing to collapse the truth before the truth has shown itself. To stay in the AND. To resist the pull to a clean verdict when the situation hasn't earned one yet.

    Marcus Aurelius didn't resolve being a powerful man who would die and be forgotten. He held the tension. Every night, by candlelight, in a tent on the edge of the empire. That's where the Meditations came from. Not from the resolution, but from the holding of that tension .

    Frankl didn't resolve the paradox of suffering and meaning. He let them feed each other, and that's what gave us a book that still reaches people eighty years later.

    The Stoics didn't resolve the dichotomy of control by being like stone. They lived inside it. Full effort, full release, both at once.

    This is the work. And it's the same work as everything else we talk about on this show. The same emotional courage that lets you feel grief without performing toughness is the courage that lets you hold two opposing ideas without flattening one. The same refusal to suppress what's real is the refusal to collapse what's complicated. It's all one muscle.

    So here's the ask for this week. One thing. Catch yourself in one premature collapse. One moment where you flatten an AND into a BUT, or where you rush to a verdict before the evidence is in. Don't fix it. Don't be hard on yourself. Just notice. Noticing is the entire practice at the start.

    And if you're up for the harder version — pick one belief you're sure of, and spend ten minutes steel-manning the other side. See what happens to you when you do.

    The world doesn't need more people who are sure. It needs more people who can stay in the question long enough to find what's actually true. That's the Stoic move. That's the courageous move. That's the move that makes you harder to fool, gentler with the people in your life, and more honest with yourself.

    Be brave and stay in the AND.

    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.coffee

    Watch 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.
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About Stoic Coffee Break
"Act on your principles, not your moods." A weekly meditation on how Stoic principles can help you be a better human. https://stoic.coffee Follow us on social media: https://instagram.com/stoic.coffee
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