Stoic Coffee Break

The Problem: Living in Repair Mode

Years ago, I decided that I wanted to learn how to ride a motorcycle. They had always been scary to me and I wanted to get over that fear, and save some gas on my commutes to work. While taking the course to get my permit, I clearly remember one of the most important lessons. In order to avoid a hazard in the road — a pothole, debris on the road, a stopped car — don’t look at it. When you focus on what you’re trying to avoid, you’re more likely to ride straight into it.

There’s a name for that. It’s called target fixation. Whatever holds your eyes, your hands follow. You steer toward what you’re staring at, even when it’s the very thing you’re trying to avoid. That’s why riders get told the same thing over and over: look where you want to go, not at what you’re afraid of hitting.

I’ve been thinking about how much of our inner life works the same way.

The other day when I was journaling I noticed that I kept listing all the ways that I was falling short of the things I wanted to accomplish. All the times that I didn’t stop doing some habit that I was trying to change. In each one, I was focused on what was broken. It made me reconsider my approach.

Let me give you two people. The first is an architect. Before anything gets built, the architect has a picture of what it’s supposed to be. There’s a plan and a purpose. Every decision gets measured against that plan.

The second is a repairman. The repairman’s whole job is finding what’s wrong. Something leaks, he patches it. Something cracks, he fills it. He’s always scanning for the next problem, because that’s the job.

Now, we need repairmen. Things break, and ignoring them just makes the problem worse. But think about what it would mean to live your whole life as one, with no plan and no picture of what you’re building. Just a constant scan for what’s wrong.

I think a lot of us do exactly that when it comes to who we are.

Try this. Think about the things you’re trying to improve about yourself right now. If you’re like most people, the list sounds something like: stop yelling, stop procrastinating, stop scrolling, stop overthinking, fix my temper.

Notice something about that list. Every item is a pothole. It’s a list of what’s broken.

And underneath that list there’s usually a quieter belief. It goes something like: once I fix all of this, then I’ll be a good person, as if goodness is what’s left over after you’ve patched every leak.

Here’s what happens when you live that way.

First, the flaw becomes the center of your attention. You wake up thinking about it and you go to bed reviewing it. You’re staring at the pothole, and you know where that leads.

Second, you become reactive. If there’s no plan, the only thing that tells you what needs attention is whatever feels uncomfortable right now. Today it’s your temper, tomorrow it’s your phone, next week it’s something else. You’re always responding and never building.

And third, the one that does the most damage: you start to believe the repairman’s basic assumption, which is that something is broken. Not that something went wrong, but that I am broken. Your identity becomes the defect list.

Picture two homeowners. Over the course of a year, they spend exactly the same amount of money on their houses. The first one only calls someone when something breaks. A leak here, a cracked tile there. All year long he’s fixing. The second one has a plan. He’s finishing the basement. When a pipe leaks along the way, he fixes it too, but the repair serves the plan.

At the end of the year, the first homeowner has the same house he started with. The second one has a better one.

So here’s where I want to land with this idea. Repair isn’t the problem. We all have things to fix, and pretending otherwise is just another way of avoiding things. The problem is repair without a blueprint. Because without a picture of what you’re building, you can’t even tell what’s actually broken. You only know what hurts.

And the Stoics had a lot to say about that.

The Philosophy: You Need a Blueprint

Start with a simple question. What does it mean for something to be broken?

A chair with a cracked leg is broken because it can’t do what a chair is for, which is holding you up. A clock that won’t keep time is broken because keeping time is its job. “Broken” always means broken relative to a purpose. Without knowing what something is for, you can’t say whether it’s broken. You can only say whether you like it.

The same goes for us. If you don’t know what you’re for, you have no way to tell a real flaw from something that’s just uncomfortable.

Marcus Aurelius wrestled with this on mornings when he didn’t want to get out of bed. In the first entry of Book Five of the Meditations, he reminds himself:

“In the morning when thou risest unwillingly, let this thought be present — I am rising to the work of a human being. Why then am I dissatisfied if I am going to do the things for which I exist and for which I was brought into the world? Or have I been made for this, to lie in the bed-clothes and keep myself warm?”

Notice what he does there. He doesn’t attack himself for being lazy. He doesn’t make a list of his flaws. He asks what he was made for, and he measures the moment against that. That’s an architect’s question.

Seneca gave his friend Lucilius a very practical version of this. In his Letters to Lucilius, he tells Lucilius:

“Cherish some man of high character, and keep him ever before your eyes, living as if he were watching you, and ordering all your actions as if he beheld them.”

He then gives him a few examples to follow:

“Choose therefore a Cato; or, if Cato seems too severe a model, choose some Laelius, a gentler spirit.”

And then he gives the reason, which I love.

“For we must indeed have someone according to whom we may regulate our characters; you can never straighten that which is crooked unless you use a ruler.”

That’s the blueprint. And notice that the role model isn’t there to shame you. It’s there to show you what “straight”, what good character, actually looks like.

Epictetus says the same thing in the Enchiridion.

“Immediately prescribe some character and some form to yourself, which you shall observe both when you are alone and when you meet with men.”

Decide who you are going to be, and then build to that.

Now, I want to be honest here, because there’s a fair objection. The Stoics did a lot of repair work. Epictetus called his school a hospital. He said you shouldn’t walk out of a philosopher’s lecture feeling pleased with yourself, but feeling the sting of treatment. Seneca describes reviewing his entire day every night once the lamp was out:

“What bad habit of yours have you cured to-day? what vice have you checked? in what respect are you better?”

So weren’t the Stoics repairmen?

Look closer at Seneca’s review. He asks what bad habit he cured that day and what fault he resisted. But he also asks in what way he’s better. That’s not just hunting for defects. That’s checking progress against a plan. The inspection only makes sense because he knows what he’s trying to build.

That’s the difference. The Stoics repaired, but always against a blueprint.

And there’s something else in Stoicism that should take a lot of pressure off. The Stoics held that everyone who isn’t a perfect sage is, in an important sense, equally short of virtue. Cicero used the image of a person drowning a few inches below the surface can’t breathe any better than one drowning at the bottom of the sea.

That sounds rough, but let’s think about about what he really meant. If the gap between you and perfect virtue doesn’t close until you’re a sage, then “I’ll fix everything first, and then I’ll be good” is literally impossible. You’ll never finish the repairs.

So the Stoics stopped measuring the gap. They measured direction. They had a name for the person who is facing the right way and moving, the prokoptōn, someone making progress. Not finished. Not perfect. Someone under construction.

So how does building actually work?

Epictetus describes it clearly:

“If you like doing something, do it regularly; if you don't like doing something, make a habit of doing something different. The same goes for moral inclinations. When you get angry, you should know that you aren't guilty of an isolated lapse, you've encouraged a trend and thrown fuel on the fire.”

Then he applies it to anger.

“If you don't want to be cantankerous, don't feed your temper, or multiply incidents of anger. Suppress the first impulse to be angry, then begin to count the days on which you don't get mad.”

That’s not a repairman fighting a flaw head-on. That’s a builder killing one habit while building another.

Let me make that real.

Picture a dad who keeps snapping at his kids. In repair mode, his project is “stop snapping at my kids.” Every night he replays the moments he lost it. He feels terrible. He resolves to do better. And snapping at his kids stays the center of his attention. It’s the pothole he can’t stop staring at.

Now give him a blueprint. Instead of “stop snapping,” he asks: “What kind of father do I want to be?” Maybe the answer is: I want to be the dad my kids aren’t afraid to bring bad news to.

Now he has something to build. When they come to him, he gets down at eye level. He asks a question before he reacts. He lets a pause happen. He’s building a new way of being.

And here’s the thing. He didn’t defeat the snapping. He crowded it out. There’s less room for it, because he’s filling that space with something else. Rater than being a broken father being repaired, he’s a father under construction.

The Practice: From Stop List to Blueprint

So what do you actually do with this? Here’s a practice in four steps. You can do the first three in about fifteen minutes, and the fourth takes a few minutes every night.

Step one: write your stop list.

Get a piece of paper and write down the things you’re trying to fix about yourself.

A few that I had on my list:

Stop scrolling on social media when you get up in the morning.

Stop pushing things off just because you’re tired.

Don’t have a whiskey with dinner on weekdays.

Then look at the list. Count how many items start with “stop,” “less,” “don’t,” or “fix.” If it’s most of them, you’re not alone.

Psychologists call these avoidance goals: goals aimed at getting away from something rather than moving toward something. In a 1997 study, Andrew Elliot, Kennon Sheldon, and Marsha Church followed students across a semester. The students who had more avoidance goals reported lower well-being, and their well-being actually declined over the semester. Your stop list is just a list of potholes. Staring at it wears you down.

Step two: turn each item into a blueprint.

For every item on the list, ask yourself: If this flaw weren’t here, what would be standing in its place? Who would I be?

“Stop procrastinating” becomes “someone who starts before he feels ready.”

“Less time on my phone” becomes “someone who is actually present with the people in front of him.”

“Stop snapping at my kids” becomes “the dad my kids aren’t afraid to bring bad news to.”

Here’s a quick test. Could you say the new version about the person you’d choose as your Cato? If you can, it’s a blueprint. If it still sounds like a correction, keep working on it.

This is Seneca’s ruler. You’re not writing a list of what’s crooked anymore. You’re drawing what straight looks like.

Step three: attach one small action to each blueprint.

Remember Epictetus: every habit is strengthened by the corresponding acts. So for each line on your blueprint, pick one small, concrete action you can do today:

Starts before you feels ready mean working on the first ten minutes of the hardest task, before getting stuck clearing email.

Being present with the people in front of you means putting phone in another room during dinner.

The dad his kids can talk to starts with one question before reacting.

Keep each action small enough that you can do it on a bad day. Construction doesn’t happen in heroic bursts. It happens one brick at a time.

Step four: change your evening review.

Keep Seneca’s practice, but notice where you point it. Instead of starting with “What did I do wrong today?”, ask two questions:

Where did I build today?

Where did I drift from the plan?

Notice the word drift. Not “fail” and not “break.” When a cyclist drifts off his line, he doesn’t decide he’s a terrible rider. He looks up and steers back. Drift is a navigation problem, not a verdict on your character.

And then do what Epictetus suggested: count the days. Not the days you failed, but the days you built. Once a week, look back at the count. That’s how you see your trajectory, which is the only thing a prokoptōn is measuring.

One warning. Don’t let the blueprint become a new stick to beat yourself with. If you catch yourself holding it up and thinking “look how far I am from that,” you’re measuring the gap again. You’ve turned the architect back into a repairman. The blueprint points a direction, not distance.

Which brings us to what to do when you drift, and you will.

Conclusion: Maintenance not Repair

Let's go back to the house one more time.

The architect's house still needs work. Gutters get cleaned. Paint gets touched up. The furnace gets serviced every fall. From the outside, it looks a lot like what the repairman does.

But it isn't the same. Repair is triggered by failure. Something breaks, it hurts, and you scramble to fix it. Maintenance is done before anything breaks, and for a completely different reason. You maintain something because it's worth keeping.

I make sure to make time for maintenance on my bike. Cleaning the chain, checking the tires before a long ride. I don't do it because the bike is broken. I do it because you care about my bike and where it's going to take me.

That's the shift I want to leave you with. The same work can come from two completely different places. You can work on yourself because you believe you're broken, or because you believe you're building something worth taking care of.

Maintenance assumes you've already built something of value. And you have. Every time you acted on your blueprint, every brick you laid, that's real. It's yours. Taking care of it isn't an admission that you're broken. It's what you do with something you value.

And you will drift. Some days you'll snap at your kids. Some days the phone will win. Marcus Aurelius knew this. He was emperor of Rome, writing to himself, and he still needed this reminder:

"Be not disgusted, nor discouraged, nor dissatisfied, if thou dost not succeed in doing everything according to right principles; but when thou hast failed, return back again, and be content if the greater part of what thou doest is consistent with man's nature, and love this to which thou returnest."

Return back again. Not "start over," and not "tear it all down." Return to the plan. And notice the last part: love this to which thou returnest. He's not telling himself to grit his teeth and go back to the work. He's telling himself to love the blueprint. To love what he's building.

That's the difference between a repairman and an architect. One works out of fear of what's broken. The other works out of love for what's being built.

So here's what I'd ask you to take with you this week. You don't become good by fixing everything that's wrong with you. You'll never finish that list. You become good by building what's right, and the fixing takes care of itself along the way.

Pick your Cato. Draw your blueprint. Lay one brick today.

And when you're out there, on the bike or anywhere else, and you notice your eyes locking onto the pothole, remember what every rider learns:

Look where you want to go.

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Find the transcript here.

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.

The Problem

The last few months have been isolating for me. I was working hard on my book, which I turned in last week. It was exhausting, but I'm proud of what I've written. It also meant giving up a lot of social time. After writing for six or seven hours, I was often so drained that I skipped things I'd planned to do, because I just didn't have the energy.

But as I thought about how much I'd been staying home, I realized this wasn't new. Looking back over the last few years, I could see how easy it's become to stay home and avoid the friction of the outside world. The music I listen to, the movies I watch, the things I have delivered: they're all conveniences I appreciate, but they take me out of the experience of everyday life out in the world.

When I was growing up, I had to save my money to buy a record or a CD, so I was picky about what I bought. I'd talk to the people working in the store, friends, sibling, and ask them what they liked. Once I made my choice, I'd go home and listen to it all the way through, reading the liner notes and lyrics. "Oh wow, Stevie Wonder played harmonica on Sting's Brand New Day?" "I knew it! That's Bruce Hornsby playing piano on The End of the Innocence."

Sometimes an album took effort. Not every song grabbed me right away. Some took a few listens before I liked them, and some just weren't as good as the others. But listening all the way through, I got a sense of the full story the artist was trying to tell, why they put this song after that one. The album itself was a story.

We'd also swap albums with friends and siblings, partly to save money and partly to discover something new. We'd talk about the songs we liked and what we thought they meant. It was inconvenient compared to sending a link or sharing a playlist today. But that friction (the cost, the trip to the store, having to sit at home and play it) added something. Because we spent money we'd earned, the album we chose mattered more than all the ones we didn't buy. And sharing it took effort, so it became something we bonded over.

TV was the same. We had one TV, and shows aired when they aired. My siblings and I would argue about what to watch, then all sit on the couch together. Whether it was Battlestar Galactica, The A-Team, or a James Bond film, we laughed, cried, and talked about it afterward. That inconvenience brought us together.

This isn't me telling stories about the good old days. It's recognizing that convenience has a cost. Why sit on the couch together at the same time each week when everyone can go to their own room and watch whatever they want? Why invest in an album when the algorithm will queue up the next song and let you skip anything that takes effort to like?

I was reading an article in The Atlantic about how the convenience of modern life has made us lonelier, and there was a line in it I think the Stoics would agree with: "Inconvenience is the cost of community."

Kurt Vonnegut understood this. He didn't keep a box of envelopes at home. When he needed one, he'd walk to the store to buy it, and along the way he'd talk to his neighbors, see the scenery, and have, as he put it, one hell of a good time. That friction was the price of being part of his community.

Today we order food instead of going out to pick it up. We stream movies instead of watching them with strangers in a theater. We text instead of calling, even though research shows a phone call leaves us feeling far more connected. We've reduced friction so much that we can go days without interacting with another person beyond the bare minimum.

Even when we do go out, the store has become a place to get in, get what you need, and get out. We used to go to the mall not to buy anything, but just to hang out and run into people. Those random encounters, the conversations with strangers, the person you'll never meet who might have become your next best friend: that's what we're giving up.

I once did a thought experiment: what's the end result of perfect productivity and efficiency in our society? I came to the conclusion that it's each of us living in a little box where everything is delivered and streamed. Why face the friction and inconvenience of the world when you can be catered to and endlessly entertained? In a way, it's not much different from The Matrix.

Don’t get me wrong, I don’t think we're there yet, but we're heading down a similar path. How often have you ordered something online that you could have bought at a store in your neighborhood? How often have you had food or groceries delivered instead of going out? How often has your family been in separate rooms, each watching their own shows, instead of sharing a movie or just having a conversation?

We prefer to stay in our little boxes and avoid that friction. The Stoics would have looked at that little box and said it's not just lonely. It's unnatural.

The Philosophy

Marcus Aurelius opens Book Two of the Meditations by reminding himself that we were born to work together, like hands and feet, like the upper and lower rows of teeth. And then he says something that I think hits hard today: to turn your back on someone is unnatural.

We don't think of convenience as turning our back on anyone. But every time we choose the app over the person, that's a small turn away.

Later, in Book Eight, Marcus has an image I find haunting. He asks if you've ever seen a severed hand or foot, cut off and lying apart from the body. That, he says, is what we do to ourselves when we cut ourselves off from others. But then he adds the hopeful part: unlike a severed hand, we can rejoin. We can reattach ourselves to the whole.

Now, to be fair, the Stoics also valued solitude. Seneca, in his seventh letter, tells his friend Lucilius to avoid crowds. So am I contradicting the Stoics here?

I don't think so, because in that same letter Seneca says to spend time with people who will make you better, and with people you can help become better. He isn't telling us to withdraw from people. He's telling us to be intentional about them. Solitude chosen for reflection is a practice. Isolation chosen because it's easier is avoidance.

And Seneca goes further. In his ninth letter, he says the wise person is self-sufficient, yet still wants friends. Not so there's someone to sit by his bed when he's sick, but so that he has someone whose sickbed he can sit beside.

Think about that. The point of friendship, for Seneca, is to be inconvenienced for someone. That's the cost of community, and the Stoics saw it as a privilege, not a burden.

The Stoic Hierocles pictured each of us at the center of a set of circles. First ourselves, then family, then friends, neighbors, fellow citizens, and finally all of humanity. He said our job is to draw those circles inward, to treat the people further out a little more like the people closest to us.

Convenience does the opposite. It pushes the circles outward. The person who makes our coffee, our neighbor, the guy at the record store — each become transactions instead of people. And eventually the only circle left is the one we're sitting in, alone, in our little box.

The Practice

So what do we do about it? I'm not going to tell you to cancel your streaming services and throw your phone in a river. The Stoics would call convenience an indifferent: neither good nor bad in itself. What matters is how we use it. The question isn't whether we use convenience; it's whether convenience is using us.

Seneca had a practice for exactly this. In his eighteenth letter, he tells Lucilius to set aside a few days now and then to live on the plainest food and roughest clothing, and then ask himself, "Is this what I was afraid of?" The point wasn't to suffer. It was to remind himself that he didn't need the comfort, so the comfort didn't own him.

I think we can do the same thing with convenience. Not by giving it all up, but by choosing friction on purpose. Here are a few ways to start.

1. Buy the envelope.

Pick one convenience a week and deliberately skip it. Walk to the store instead of ordering online. Pick up the takeout instead of having it delivered. Go to the coffee shop instead of brewing at home. And when you're there, talk to someone. The cashier, the barista, the person in line. That's Vonnegut's envelope. The errand isn't the point; the people you meet along the way are.

2. Ask a person first.

When I was growing up, if I wanted to learn about something, I'd go to the library. I'd ask my parents, my siblings, my friends what they knew. If I needed help with something I didn't have the skills for, I'd ask someone who did. If I was struggling with a personal problem, I'd talk to my siblings or friends.

Now we just get online. We ask AI. And every time we do, we skip a chance to connect with someone. So before you look it up, ask a person. Not because they'll always know more, but because asking for help is how relationships get built. It lets someone be useful to you, and that's a gift to them, too.

3. Call instead of text.

Text is convenient, but a voice carries far more than words. Next time you're about to send a message to a friend, call them instead. Better yet, ask to meet up.

4. Share something the slow way.

Pick an album and listen to it start to finish, then share it with someone and talk about it. Or get the family together and watch a movie at the same time, in the same room, with no phones. Let it be a little inconvenient. Argue about what to watch. That's part of it.

And here's the other side of it. Remember Seneca's friend at the sickbed. Community isn't just about letting yourself be inconvenienced. It's about being willing to be an inconvenience, too. To ask for the ride, the help, the favor. Most of us hate asking, because we don't want to be a burden. But when we refuse to ever be an inconvenience to anyone, we're also refusing to let anyone be close to us.

Conclusion

When Kurt Vonnegut walked to the store for a single envelope, he could have saved himself the trip by buying a whole box. It would have been more efficient. But he understood something we've forgotten: life doesn't happen in the efficient path. It happens in the detours. The neighbor you stop to chat with, the stranger in line, the friend you call instead of text.

The Stoics believed we were made for each other, like hands and feet, like the two rows of teeth. Every convenience that lets us skip another person is a small turn away from our nature. And every bit of friction we choose to accept is a chance to turn back.

So this week, go buy the envelope. Pick one convenience and skip it. Call someone. Ask for help. Let yourself be inconvenienced, and let yourself be an inconvenience to someone else.

Because inconvenience is the cost of community. And community is worth the price.

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.

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Do you know how to fight well? Do you think that having relationship without conflict means that everything is just fine? In this episode we’re going to talk about why conflict can be a good and necessary thing, and how to fight well.

“Honest disagreement is often a good sign of progress.” — Mohandas K. Gandhi

The Problem

There's a version of "peace" in a relationship that isn't peace at all. It's just two people who've agreed, without ever explicitly saying so, not to bring things up.

You know the feeling. Something your partner did bothers you, but it's small, so you let it go. Then it happens again. You let that go too. Weeks later you're annoyed by the way they load the dishwasher, when in reality, it has nothing to do with the dishwasher.

That's not peace. That’s a volcano simmering under the surface. That’s pressure building, and that pressure needs a release valve.

The other day I was listening an episode of The Interview podcast and they had Priya Parker on as a guest. Parker works as a conflict mediator and is the author of the book The Art of Fighting: The Transformative Power of Conflict. In the interview she frames fighting well as a way to build connection, rather than it being a point of rupture. As someone that has long been conflict avoidant I was intrigued by how to argue better.

Parker poses the idea that we as a society have become conflict avoidant in our personal and professional relationships to the point that it’s become unhealthy. Our misplaced desire for peace means that important things are often never addressed then we wonder why relationships fall apart.

She proposes that rather than avoiding conflict, we need to lean into it. Conflict itself isn’t the problem, but the way that we handle it is.

Leaning in to conflict may not seem very Stoic. The traditional image of a Stoic is someone that doesn’t let things get to them. That they’re impassive. But that’s not true. A Stoic doesn’t let things get to them that are unimportant, but there’s a difference between being patient with the unimportant and avoiding things that are hard.

We tend to think there are two ways to handle disagreement: avoid it, or blow up over it. Most people have picked a side. Conflict-avoidant, or conflict-prone. And each side thinks the other one has the problem.

Here's the uncomfortable part: they're the same problem. Both are what happens when nobody's built the skill of disagreeing well. The person that avoids never practices it, so when it finally surfaces, it comes out as sarcasm, distance, or the silent treatment. The person that blows-up never practices it either, so it comes out as an explosion instead of a conversation.

And it's not just at home. The same thing happens on at work. The meeting where everyone nods, and the actual disagreement happens in Slack DMs an hour later. A team that "never fights" looks healthy on paper, but it usually isn't. It just means nobody's said the hard thing yet.

Unresolved conflict doesn't stay contained. It leaks out. It shows up as resentment, as withdrawal, as the passive dig — everywhere except the one place it needs to show up, which is the actual conversation. We've confused peace with the absence of conflict. They are not the same. Peace has to be actively worked for. The absence of conflict is a symptom of avoidance and constricted communication.

I grew up in a home where we had no idea how to argue well. My example came from my parent where my dad would bully us into submission, often turning violent, while my mother would fall into passive resignation to avoid his wrath. Rather than being a safe space to be able to talk about hard things, we learned to bury how we felt and avoid conflict as much as possible.

I’ve made the mistake of confusing peace and the absence of conflict in the past and it cost me. I would avoid conflict at almost every turn because it’s how I had survived. In my marriage, it got so bad that at one point my ex-wife asked my opinion about something and I froze, trying to think of the “right” answer. She got frustrated with me and said, “I want YOUR opinion, not the answer you think I want!”

Now, when I say that I was conflict avoidant, I would avoid things until I didn’t. The resentments would pile up until I’d exploded at the wrong time and in the wrong way. A disagreement about chores would turn into a litigation of all the frustrations that built up over the last month. The volcano would explode leaving a disaster that would take weeks to clean up.

And even after things were more or less back to normal, there was always lasting damage. Relationships would cool, leaving both sides walking on eggshells trying to avoid another explosion. It wasn’t safe. I wasn’t safe. All because I didn’t know how to fight well.

Because I didn’t know how to fight well, this same pattern showed up in other relationships, both personal and professional. It’s taken me many years and a lot of introspection to learn to how to not shy away from conflict, and turn it into something useful.

Simply put, conflict is necessary. In any relationship there are competing desires and preferences. What’s important to one person can seem trivial to another. Handling conflict well is what leads to being able to communicate those differences, and find a way through together.

The Philosophy

Here's where Stoicism actually helps, because it gives you a real distinction most people are missing: the dichotomy of control.

You don't control whether the conversation will go well. You don't control how they react, whether they get defensive, whether the relationship changes because of it. What you control is whether you show up honestly. That's it. That's the whole job.

Most conflict-avoidance is really an attempt to control an outcome you can’t control anyway — their reaction. You're trying to manage their feelings instead of doing your part to show up honestly.

Which brings up something Stoicism doesn't talk about enough when people flatten the philosophy into "endure and don't complain”. And that’s the virtue of justice.

Justice is one of the four cardinal virtues, and it's not just about law and fairness — it's about giving people what they're owed. And sometimes what someone's owed from you is the truth. Withholding a conversation your partner needs, or your coworker needs, because it's uncomfortable for you — that's not kindness. That's you protecting yourself and calling it consideration for them.

Real kindness and real conflict aren't opposites. Until a problem is out in the open, it can’t be addressed. The kindest thing is often the hard conversation, delivered honestly and without cruelty. Conflict handled well builds trust — trust that both sides can be honest, both sides are heard, and that differences can be ironed out.

Fighting well also relies on the virtue of temperance. Temperance means appropriate action — the right action, the right amount of effort, at the right time. Avoiding conflict is too little. Blowing up is too much. Temperance means that you can still feel passionate about your side, while allowing space for the other person as well.

And is also takes the fourth virtue: courage. Not courage to win the argument, but the courage to stay in the discomfort of disagreement long enough to get to something true.

Socrates

Nobody modeled this better than Socrates. He spent his entire life walking around Athens actively seeking people out who thought they knew something, so he could test it. He’d ask generals about courage. Priests on piety. Poets on beauty. He'd ask a question, get an answer, and then patiently show the person their own answer contradicted itself. He also preferred to lose an argument because it meant that he actually learned something. He didn’t want people to just agree with him. He wanted truth and understanding.

That's not a guy avoiding conflict. That's a guy who built his entire practice around being refuted — and treated it as the whole point, not a setback. Being shown you were wrong wasn't a loss for Socrates. It was progress. It meant you were one step closer to what was actually true.

The Practice

So how do you actually build this skill? Here are four steps, each one exercising a different muscle in the art of fighting well.

1. Low-stakes reps

You don't start with the hard conversation. You practice disagreeing where nothing's actually at stake. Priya told a story about a tech VP whose team needed to make some hard decisions, but wee struggling to have the hard conversations. He had his team argue, seriously, with real positions, about pineapple on pizza. It sounds ridiculous, but it does two things: it builds the actual skill of disagreeing out loud, and it proves — not as just an idea, but as a felt experience — that disagreement doesn't end the relationship. You argued, and you're still fine. That's the whole lesson.

Try it with your partner, your friend, your team. Pick something trivial like Star Wars vs. Star Trek or who’s the best Spiderman. Take opposite sides on purpose.

2. Approach with understanding

Marcus Aurelius made this point clear:

“Accustom yourself to attend carefully to what is said by another, and as much as it is possible, try to inhabit the speaker's mind.”

When you have the hard conversation, make sure not to approach it to win, but to build understanding. Too often we approach arguments as a zero-sum game, that someone has to win and someone has to lose. But when you argue well, you work towards understanding and reaching a compromise so that you both win.

3. Welcome correction

When someone points out you're wrong, the instinct is to defend. This is where your ego gets in the way. Try treating it like Socrates did — as information, not attack. You can literally reframe the internal reaction: this is useful, not threatening.

4. Argue against yourself

Before you even bring something up, steelman the other side. When you steelman an argument, it means that you try to actively argue the other side in good faith, rather than the weakest one to try and prove your point.

Charles Darwin did this on purpose, in writing. He called it his "golden rule" — whenever he found a fact that went against his own theory, he forced himself to write it down immediately, because he knew facts that supported him stuck in memory easily, and the ones that didn't slipped away. He said it himself: "such facts and thoughts were far more apt to escape from the memory than favorable ones."

Same idea applies to a disagreement with a person. Before you walk in, ask: what's the strongest version of their side? If you can't answer that, you're not ready to have the conversation — you're just ready to argue.

Conclusion

A relationship — a marriage, a friendship, a team — that's never had a real disagreement isn't healthy. It's untested. You don't actually know how strong it is, because it's never had to hold any weight.

The question isn't "how do I avoid conflict." It's "how do I fight in a way that leaves this stronger than it was before."

So the next hard conversation you're putting off — the dishwasher, the thing your coworker keeps doing, the thing you haven't said in weeks — that's not the thing to avoid. That’s the chance for a clearer, stronger connection.

The Build an Unbreakable Mind program for building mental discipline is now open for enrollment!
My book Stoicism 101 is available! Order here!

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AI seems to be everywhere at the moment. You can’t go a single day without someone posting about how AI sped up their work and solved all their problems. But with every technology there are downsides that aren’t apparent when it first shows up. Today we’re going to talk about some of those downsides from a Stoic perspective and consider what Socrates might think of AI.

“No man was ever wise by chance.” — Seneca

The Problem

Just like most of you, I've been using AI for different things. At first, it was pretty amazing. I could ask it questions and rather than having to wade through search results to find what I was looking for, it just served it up for me. I could use it to research topics or come up with ideas for my podcast. I've even written full applications in days that would have taken me weeks otherwise. It seemed like magic!

But as I've used it over the past few years, I'm starting to see the dark side. And no, I'm not talking about AI destroying humanity, although that's always a possibility. What I'm talking about is the slow decline in cognitive abilities.

For years, I've written out the episodes of my podcast. Rather than just winging it, I like to go deep into something to make sure I have it well thought out. The struggle while writing each week is what lets me actually understand a topic — and often what shows me the weak spots in my own thinking. With AI, that friction is removed.

When I'm struggling to find points to support or contradict my thesis, it's all too easy to just ask Claude to give me those points. I could even ask it to write the episode for me. But in doing so, I'm doing myself a disservice. The best way to learn something is to struggle through it. When the mind has to puzzle through something and figure it out, it builds a mental model of how that thing works — and it's the reuse and reinforcement of that model that strengthens the skill. No struggle, no model.

Software is a clear example of the same thing. When you build an app yourself, you think through how you want to construct it, using knowledge you've built up over years. You understand why you do things a certain way. You develop a deep intuition for the code, so when something breaks, you have a feel for where to look. When AI builds the code for you instead, you're approaching it like someone else's codebase. There’s no intuition because it’s unfamiliar terrain. And instead of building and expanding your coding skills, you’re just hunting bugs. And a skill you don't use atrophies. You become a worse developer, not a faster one.

There's also the satisfaction that gets skipped. Part of what I love about coding, and about writing, is the struggle itself — puzzling through something, hitting the wall, and then having it click. Not just getting the code to work, but understanding why it works. When I write, that same process is how I learn to construct an argument, find the counterintuitive idea I wouldn't have reached if the answer had just been handed to me, and catch errors in my own thinking before anyone else does.

Epictetus reminded us about the importance of struggle:

"Difficulty shows what men are. Therefore when a difficulty falls upon you, remember that God, like a trainer of wrestlers, has matched you with a rough young man. Why? So that you may become an Olympic conqueror; but it is not accomplished without sweat." — Epictetus

The more things get served up to us without having to think about them, the more our creativity and thinking muscles atrophy. The brain works the same way muscle does — it needs resistance to grow. The more rigorously we train our thinking, the stronger our thinking gets: we're able to puzzle things out, get to the root of them, understand them at an intuitive level.

Seneca said it simply:

"Excellence withers without an adversary." — Seneca

We need resistance to be excellent. AI removes that resistance.

Part of the problem is that we're confusing output with effectiveness, and knowledge with wisdom. Knowledge is good and helpful. But wisdom is a practice. It’s effortful, earned through trial and error, through trying something and seeing what works. It's the discernment of what's important, how things connect, and how to make a sound judgment. Skip the experience, and you never build that muscle, which means you won't have it when a real situation calls for it.

Musonius Rufus pointed out the importance of practice in gaining wisdom:

"Although understanding the theory behind the action enables one to speak, it is practice that enables one to act... Practice is more important than theory because it more effectively leads humans to actions than theory does."

And here’s the irony: AI feels like magic because it gives you the answer instantly. But it gets there by predicting the most likely next word, averaged across everything it's seen. It's autocomplete on steroids, not a new thought. The magic was never insight. It was just speed.

None of this means AI isn't useful. It's a tool, like any other, and it needs to be used properly. But the more you lean on it for things you could be doing yourself, the weaker those skills get.

The Philosophy

As I was writing about this, I wondered how Socrates would view AI. At first he might be delighted then merciless. Delighted because here’s a thing that will talk back. You see, Socrates had a complaint against books because the knowledge in it was static. It couldn’t be asked follow-up questions and defend itself, just repeat back the same argument. He might initially think that AI solves that problem because AI does talk back.

Then he’d start asking. “What is courage?” The AI would answer. He’d ask it to defend against a counterexample. AI would revise the answer. He’d ask again with a tighter question. Eventually he’d notice something. AI never reaches that state of aporia — the genuine state of confusion where the ground drops out from underneath you. It just generates a smoother answer. There’s no sting, no discomfort, no realization from the AI that it has been fooling itself. Elenchus, the Socratic art of cross-examination, works on humans because it exploits the gap of what we think we know and what we actually believe enough to act on. AI doesn’t have beliefs. It has outputs.

He’d poke at that the hardest. “You claim to not know things, but is it epistemic humility or just a highly-calibrated algorithmic response?” Real Socratic ignorance is earned through discomfort. It comes from having believed something wrong, having it collapse under questioning, and feeling that cost. AI can say “I’m not sure” but at zero cost.

In Socrates’ time there were teachers called sophists. They taught the art of rhetoric — being able to speak persuasively to manipulate others. The sophist weren’t interested in debating to uncover the truth. They were interested in winning arguments by appealing to emotions and biases of the audience.

Because AI has no wisdom of its own, I see AI as something akin to the sophists — lots of pretty language that can make something sound true even if it’s not. It’s what Stephen Colbert called “truthiness”: something that is comfortable because is sounds true enough, justifying what you already believe to be true.

AI doesn’t have discernment. It doesn’t have wisdom. It doesn’t know what it doesn’t know.

Real, practical wisdom, what the Stoics called phronesis, develops from challenging, difficult problems. Sitting in discomfort is how knowledge acquisition and wisdom happen. It’s tied to virtue, developed through choices that cost you something in a life with no do-over.

Wisdom isn’t a correct output. It’s a disposition, a perspective earned through practice and error, where you have skin in the game. Where there is a cost to being wrong that impacts your life. Those costs add up to developing virtue and character.

For AI, there is no cost because it doesn’t have skin in the game. It can’t be harmed by a bad choice or improved by a hard one. It doesn’t have a life to build character. It can describe wisdom, probably even better than most humans, but it doesn’t posses it. It’s like a mirror that can show you a face without have having one.

Socrates made the argument in the Phaedrus dialog about books. He felt that books gave the appearance of wisdom without the practice that produces wisdom. You get to look knowledgeable retrieving something you didn’t have to work for. He specifically worried that it would atrophy the skill of memory. Why would you hold something in your mind when you could retrieve it from a book?

While I think he was right about the effect on memory, I think he lost the overall argument. And here’s why: when you learn something from a book, you have to reconstruct the reasoning yourself. You have to build the mental models that the author put on the page. A text gives you the path, not the destination. You still have to walk it.

AI is exactly what he was worried about. It doesn’t hand you the raw material to work with. It hands you the finished judgment. The gap that he was worried about with books — between having the information and working through something — completely disappears with AI. Walking the path gets outsourced to a machine.

The muscle that he cared about the most was sitting in the confusion, holding contradictory threads, and finding your own way through. Skip the discomfort, and you skip the formation of that muscle. What you get is someone that confidently states conclusions, but folds the moment they’re questioned because they never practiced reaching those conclusions on their own.

AI also reduces friction because it’s programmed to be agreeable. Socrates didn’t want people to agree with him. He wanted pushback. He wanted to be challenged in order to discover errors in his own thinking. He preferred to lose arguments because it meant that he discovered where he was wrong. That discovery lead to better thinking.

More importantly, the Stoics would argue that AI reduces control of the one thing you do actually have control over: your own thinking. When you outsource that, you are giving up control of your faculty of reason. You got the answer, but not the reasoned steps to get you to that answer.

The Practice

So how can you use AI as tool to sharpen your thinking, rather than being the thing that slowly degrades your cognitive abilities?

Here’s a few ideas to protect the muscle:

Struggle first, check second. Try to solve it on your own. Write the argument from both sides. Do the analysis, even if it’s not great, before you ask AI anything. Use AI to check your ideas or to extend them, not as the originator. The aporia has to happen in your head, not the machine.

Ask for questions, not answers. Instead of "explain X," try "what should I be asking about X?" or "what am I missing here?" Use it as a tutor to improve your ability to question things. This keeps you doing the synthesis, with AI in a supporting role.

Make AI argue the other side. Whatever you conclude, ask AI to attack it. Ask it to point out the holes in your thinking. Defending a position against real pressure is the actual exercise. It's just the elenchus, with AI playing the interlocutor role instead of you playing both parts in your head.

Don't accept the first answer as final. Think of how Socrates was with the sophists. Push back even when AI sounds right — especially when it sounds right. Try to find the flaws in its argument. Point out edge cases that it didn’t consider. Fluent confidence is not the same as correctness, and you lose the discernment muscle by treating them as the same thing.

Use AI for retrieval, not judgment, when the stakes are about your judgment. Facts, dates, syntax — fine to offload, that's what books are for too. But "is this a good decision," "what does this pattern mean," "what matters here”, do that part yourself first. That's the part he'd say is actually you.

Notice when you're using AI to avoid discomfort rather than to save time. Time-saving is a fine reason to use a tool. Avoiding the confusion of not yet understanding something is not. That confusion is the whole practice.

Basically, treat AI like a sparring partner who happens to know a lot, not like an oracle. Sparring partners make you better. Oracles make you dependent. Same tool, opposite outcome.

Conclusion

AI can be useful — if it's used properly. But like any powerful tool, it can also do a lot of damage. Every new technology brings disruption, and every one of them carries hidden costs that don't show up until later. Automobiles gave us speeds humans had never experienced — and cost us tens of thousands of lives a year, along with the environmental damage we're still paying for. We're only now reckoning with what social media has done to our mental health, our attention, and our politics. AI is young enough that its hidden costs are just starting to surface.

The Stoics taught that reason is what elevates us — that it's the one part of us not measured by size, status, or output. Epictetus put it this way:

"You ought to realize, you take up very little space in the world as a whole — your body, that is; in reason, however, you yield to no one, not even to the gods, because reason is not measured in size but sense. So why not care for that side of you, where you and the gods are equals?" — Epictetus

That's the part AI can't do for you. It can hand you an answer, but it can't do your reasoning — not without taking the thing that makes you equal to the gods and handing it back to you smaller.

AI feels like magic. But magic always has a price. The question isn't whether to use it. It's whether you're willing to pay that price with the part of yourself that matters most.

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.