Stoic Coffee Break

Certainty and hubris have always been part of being human. It feels good to be certain, to believe that your opinion is the right one. We like leaders who sound certain and shun those that don’t. But sounding right isn’t the same thing as having the truth. What if the actual way to truth is not through being certain, but by embracing uncertainty?

“It is impossible for a man to learn what he thinks he already knows.” ― Epictetus

The Problem

We live in an age of certainty.

Open any social media app and within seconds you’ll be hit with confident declarations on politics, relationships, health, ethics, all delivered with the kind of conviction that leaves no room for doubt. Hot takes are presented and settled truth. The more confident the claim, the more it spread.

Certainty is the currency of attention.

But here’s the problem: certainty is is a trap. It’s one of the more dangerous traps that we can fall into. Not just personally, but as a society.

When we’re certain, we stop questioning. We stop listening. We lose our ability to sit with complexity and nuance. To consider that we may not be seeing the whole picture. We trade wisdom for the comfort of feeling right.

That comfort is seductive. We like certainty because it feels safe. Ambiguity triggers the same neurological response as physical danger. Your brain would rather have a wrong answer than no answer at all. Uncertainty feels like we’re in the dark. Certainty feels like turning the light on, even if what we see is distorted.

But the cost is enormous. Certainty damages relationships because if you already believe you have the truth, you can’t hear anyone who sees things differently. It damages communities because it turns disagreements into threats. And it damages your own capacity for growth. As Benjamin Franklin reminds us:

“The doorstep to the temple of wisdom is a knowledge of our own ignorance.” — Benjamin Franklin

Being able to sit in uncertainty, to acknowledge your ignorance, is where wisdom starts. Wisdom only comes to someone who is willing to be wrong.

We don’t live in a black and white world, but certainty insists that we do. This isn’t a new problem. The ancient world wrestled with it too, and in one of Athens most cautionary tales, certainty brought down one of the world’s greatest civilizations.

The Philosophy

To understand the danger of certainty, we need to got back to 5th century BCE Athens. What happened there maps almost perfectly to what we’re going through right now.

Like us, Athens was a democracy, which meant that political power belonged to whoever could best persuade the crowd. In this environment were a group of professional teachers called the Sophist.

The Sophists were the original political spin doctors. They traveled from city to city teach rhetoric, the art of persuasion. But here’s the critical distinction: the didn’t teach people to discover the truth. They taught how to win arguments. How to make the weaker case appear stronger. How to use language to emotionally manipulate people, regardless if what was being spoken was true.

In one of Plato’s dialogues, Socrates confronts the Sophist Grogias. Gorgias claims rhetoric is the greatest of all arts because it can convince anyone of anything. Socrates’ response is brutal: rhetoric without truth is flattery. It’s the difference between a doctor and pastry chef. One tells you what you need to hear. The other tells you what you want to hear.

One of the more famous Sophist, Protagoras, said, “man is the measure of all things.” In other words, the truth is relative. There is no objective truth. Only what you can convince others to believe. That idea, weaponized by skilled rhetoricians and handed to skilled politicians, was extremely dangerous. And the politicians lined up to learn it.

This was the environment that Socrates lived in, and he found it repugnant. Socrates had an entirely different starting point. When the Oracle at Delphi declared him the wisest man in Athens, he was genuinely baffled. So he went out to test it. He spoke with politicians, poets, craftsmen — anyone with a reputation for wisdom. And what he found was consistent: they all believed they knew things they didn't. They had mistaken confidence for knowledge.

His conclusion was humble: his advantage was knowing that he didn't know. To Socrates, that awareness, that gap between what we think we know and what we actually know, is the beginning of all genuine wisdom.

He even stated:

“I know that I am wise because I know that I know nothing.”

This is the practice we now call the Socratic method. Not debate. Not rhetoric. Disciplined questioning, that is designed to expose false certainty, including his own.

The Sophists hated it. Because Socrates wasn't playing the same game. He didn't care about winning. He cared about truth. And in a culture increasingly addicted to persuasion, that made him dangerous.

It eventually got him killed.

The Trial of Socrates

In 399 BCE, Socrates was put on trial for impiety and corrupting the youth of Athens. His accusers used exactly the tools the Sophists taught — emotional appeals, crowd manipulation, confident declarations. And Socrates, true to his philosophy, refused to fight fire with fire. He wouldn't flatter the jury. He wouldn't perform certainty he didn't have. He argued his case with the same disciplined honesty he'd practiced his whole life.

He was convicted and sentenced to death.

Certainty won. Truth lost.

The Sicilian Expedition

But the consequences of Sophist-influenced certainty weren’t limited to one man's execution. They played out at a civilizational scale in what historians consider one of the greatest strategic disasters in ancient history.

In 415 BCE, Athens voted to invade Sicily. The campaign was championed by Alcibiades, a charismatic, brilliant, Sophist-influenced general who was absolutely certain the expedition would succeed. His confidence was intoxicating. The Athenian assembly, swept up in collective certainty, voted yes despite almost no strategic justification. The one voice of caution, the general Nicias, was overruled.

The entire Athenian fleet was destroyed. Tens of thousands of soldiers lost. Athens never fully recovered. It was the beginning of the end of Athenian power.

That is what happens when persuasion beats wisdom at a civic level. When certainty is more valued than careful thought.

The Stoics

The Stoics, who came roughly a century after Socrates, inherited his epistemic humility and built it into the foundation of their philosophy.

The Stoics picked up Socrates' practice of questioning everything and formalized it. Epictetus makes clear that the first discipline is the discipline of assent. You don't just accept impressions, you interrogate them:

“You can process in your intellect and senses a wealth of thoughts and impressions simultaneously. There are impressions that you assent to, others that you reject; sometimes you suspend judgement altogether.” — Epictetus

Marcus Aurelius writes repeatedly about suspending judgment. The Stoic concept of kataleptic impression (a true, reliable perception) was important precisely because they understood how hard it is to actually know something.

Where the Sophists said truth is whatever you can convince people of, the Stoics said the first obligation of a rational person is to interrogate their own impressions before accepting them. You don't just receive an idea and run with it. You examine it. You question it. You ask whether what you're seeing is actually true, or whether you're being moved by emotion, by habit, or by someone else's rhetoric.

Marcus Aurelius, writing in his private journal, returns to this again and again. In Meditations, he writes something remarkable for the most powerful person on earth:

"If someone is able to show me that what I think or do is not right, I will happily change, for I seek the truth, by which no one was ever truly harmed. It is the person who continues in his self-deception and ignorance who is harmed." — Marcus Aurelius

Think about that. The most powerful man in the world, holding his beliefs lightly enough to be corrected. That's philosophical courage.

Seneca makes a parallel point about consuming ideas. In his Letters to Lucillius, he warns against absorbing too many opinions without digesting them or taking the time to develop you own discernment:

“It is not how many books thou hast, but how good; careful reading profiteth, while that which is full of variety delighteth.” — Seneca

It’s the ancient version of doom-scrolling through confident hot takes and mistaking exposure for understanding.

And the politicians who traded in certainty? The Stoics were clear-eyed about them too.

Thucydides, the great Athenian historian, wrote about a demagogue named Cleon with barely concealed contempt. Cleon was loud, certain, and crowd-pleasing. He argued for the extermination of the entire population of Mytilene after a revolt. The Athenians voted yes, whipped into certainty by his rhetoric. They reversed the decision the next day, barely in time to stop a massacre.

The Sophist playbook hasn't changed in 2,400 years. We see it in our own politics today. Confident framing. Simple villains. No room for complexity or nuance. The certainty itself is the product. It makes followers feel safe, chosen, and correct. Questioning it feels like betrayal.

You would think with all the advances we’ve made as humans we would have moved past this. That we would adopt a more logical and rational way of conducting ourselves. But while technology and society have advanced in many ways, human nature hasn’t. In fact, the ability to exploit human nature has gotten worse.

The Sophists were dangerous to Socrates not because they were wrong about everything, but because they didn't care about being right. They cared about being convincing. That distinction matters enormously and maps perfectly to modern media.

Demagogues, politicians, and influencers, use modern media to exploit our desire for certainty. Masses are moved not by what is actually good and virtuous, but by what they can be convince of. Those with power, wealth, and influence use this to advance their own agendas, rather than well-reasoned virtuous choices that contribute to the greater good.

And looking arrund, you don't need me to tell you where you see that today. You already know.

The Practice

So why is certainty so seductive? If it's this destructive to us personally and as a society, why do we keep reaching for it?

Because it does something powerful for us. And we need to understand what that is before we can do anything about it.

The first thing certainty gives us is identity. When a belief becomes not just something you hold but something you are, questioning it feels like self-destruction. I saw this growing up in a high-certainty religious environment. The entire framework was built around having "the truth”, with a capital T.

And that certainty wasn't just theological. It extended into everything. Your community, your family relationships, your sense of purpose and meaning — all of it rested on the foundation of being certain. Doubt wasn't just uncomfortable. It was an existential threat. Because if you were wrong about this, what else were you wrong about? Who were you without it?

That's not unique to any one religion or ideology. It's the structure of all high-certainty systems. The belief and the identity become fused, and once that happens, evidence stops mattering. You're no longer evaluating truth. You're defending yourself.

The second thing certainty gives us is belonging. In any tribe, whether religious, political, or ideological, certainty is the price of admission. Expressing doubt signals that you might not be fully committed. That you might be a threat. Communities enforce certainty not because they're malicious but because shared belief is the glue that holds them together. Questioning it publicly is a social risk most people aren't willing to take.

The third thing certainty gives us is status. Confidence reads as competence. This is well documented. People consistently rate confident speakers as more credible, even when they're wrong. The Sophists knew this 2,400 years ago. Every cable news anchor, every algorithm-optimized headline writer, every podcaster who leads with a hot take knows it. Certainty performs well. Nuance doesn't.

So how do we fight something this deeply wired into us?

The Stoic answer is practice. Deliberate, repeated, uncomfortable practice.

Practice 1

The first practice is to pause. Before you share a confident claim, repost a video, or repeat that hot take, stop. Ask one question: how do I actually know this is true? Not "does it feel true?" Not "do people I respect believe it?" But what is the actual evidence? This is the discipline of assent in daily life. It only takes a moment, but it changes everything.

Practice 2

The second practice is inversion. When you find yourself certain about something, ask: what would have to be true for the opposite position to be right? Not to change your mind necessarily, but to genuinely understand the strongest version of the counterargument. If you can't articulate it, you don't actually know what you believe.

Practice 3

The third practice is deliberate exposure to disagreement. Find one credible voice that sees your most confident belief differently. Not a strawman argument putting forth the worst version of the opposing view. Find the most serious, thoughtful person who disagrees with you. Read them. Deeply.

John Stuart Mill wrote one of my favorite quotes ever that clearly explains why this is important:

“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

This is what Socrates did. He went looking for people who might prove him wrong. He believed it was better to lose an argument learning the truth, than win and still be ignorant or wrong. That's not weakness. That's intellectual honesty.

Practice 4

The fourth practice is media literacy as a Stoic discipline. When you encounter a confident headline, treat it the way Epictetus treated impressions. Don't accept it immediately. Ask who benefits from certainty here. Ask what's being left out. Ask whether the confidence in the framing is proportionate to the actual evidence. Certainty in headlines is almost always a sales technique. You're being sold a feeling of knowing. The Stoic practice is to notice that and step back from it.

None of this is comfortable. Sitting with uncertainty, holding your beliefs lightly, genuinely entertaining the possibility that you're wrong, these things feel like weakness in a culture that rewards confident declarations.

But here's what I've learned: the people who've actually done the work, who've examined their beliefs, who've been willing to be wrong, who've rebuilt their understanding on something more honest, have a kind of groundedness that those who certain never do. Because their foundation isn't the belief itself. It's the integrity of how they arrived at it.

That's what Socrates had. That's what Marcus Aurelius was practicing in his journal. That's what the Stoics were pointing at.

Not the comfort of certainty, but the courage of honest inquiry.

Conclusion

Socrates was the wisest man in Athens not because he had the most answers, but because he was the most honest about what he didn't know.

He lived honestly in a culture that punished it. He practiced disciplined uncertainty in a world that rewarded confident performance. And it cost him everything — his reputation, his freedom, and eventually his life.

The Stoics carried that torch forward. Not as martyrs, but as practitioners. They built epistemic humility into a daily discipline. The pause before assent, the interrogation of impressions, and the willingness to be shown they were wrong. Marcus Aurelius did it on a battlefield, running an empire, and under constant pressure to project certainty that was expected of an Emperor. He still wrote, privately, that he was willing to be corrected.

That's the standard. Not perfection. Not permanent doubt about everything. But the ongoing practice of holding your beliefs honestly, lightly enough to examine them, and seriously enough to act on your best current understanding.

We live in a world that is going to keep selling you certainty. The algorithms reward it. The politicians weaponize it. The headlines traffic in it. And some part of your brain is always going to find it appealing, because uncertainty is uncomfortable and certainty feels like solid ground.

But solid ground built on false certainty is just a comfortable trap, keeping you in ignorance.

The Stoic path, the honest path, is harder. It requires you to sit with not knowing, and say "I might be wrong about this." It means that you genuinely listen to people who see it differently, and interrogate the confident claims that confirm what you already believe just as rigorously as the ones that challenge you.

This week, pick one belief you hold with certainty, and ask yourself honestly: have I ever really tested this? Have I sought out the strongest counterargument? Do I know this, or do I just believe it?

You don't have to change your mind. You just have to be honest about the difference between knowing and believing.

That's where wisdom starts.

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Michael has built a career at the intersection of data, teaching, and strategy. Always circling the same question: “How do we make better decisions amid a complex reality?” Throughout his career, he has helped people uncover the deeper structures beneath their most pressing challenges.

Michael’s perspective draws from an uncommon combination of experience. Over twenty years in consulting, data, and technology taught him to think in systems. Five years as an adjunct professor sharpened his ability to make complex ideas accessible to anyone willing to learn. Nearly twenty-five years as a poker player gave him a visceral understanding of variance, probability, and the limits of control. Those lessons echo throughout these pages.

He is the creator of The Stoic Systems Thinker, a newsletter where ancient Stoic philosophy meets modern systems thinking, and new book by the same title. At the core of his work is a belief he keeps testing: wisdom isn’t a mystical gift reserved for the few, but an emergent property of a well-designed life system. The ideas in this book have been tested in conference rooms, classrooms, and at the poker table, and they’ve shaped the way he lives his own life.

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.

Habits are a key part of our lives. We have helpful habits that help us accomplish what we set out to do. We also have some that we’d like to get rid of. But what if I told you that sometimes one good habit is all it takes to reorient our lives and make lasting changes? In this week’s episode we’ll discuss the importance of keystone habits and how you can find yours.

"All our life, so far as it has definite form, is but a mass of habits." — William James

I love to cycle. Ever since I watched the Kona Ironman competition on TV on 2003, and decided that I wanted to be that hardcore, cycling has become become a key part of not just my weekly workout routine, but a core part of my identity. While for some it may sound like torture, a 35 mile ride on a warm Saturday is my idea of an afternoon well spent.

But what this one habit brings to my life is far more than just fresh air and great legs. It influences other areas of my life in profound ways. You see, when I started training for triathlons, I was not what a triathlete should look like. I was out of shape. At 195 pounds (about 88 kilograms for you non-Americans) and only 5’7” (170 cm) tall, I was carrying a lot of extra weight. I had bad eating habits, preferring Mt. Dew over water. I could barely run a 5k in under 35 minutes. In high school I could do it in half that time.

But once I started down that path, it became the centering principle of my life. I would ride my bike to work, often taking the long way home. I changed my diet to healthier food and smaller portions. When I would go out to eat, I would divide my meals in half, setting aside the second half for home, so I wouldn’t overeat. Because I was working out more, I slept better.

And while I only competed in a single short course triathlon before focusing on just cycling, it changed the direction of my life. My gym routine, my diet, my alcohol consumption, and my sleep are all in service to helping me maintain my fitness for the bike. This in turn keeps me healthy, functional, and feeling better mentally.

This is what Charles Duhigg, the author of The Power of Habits, calls a “keystone habit”. In short, it’s a core habit that influences other behaviors. It reenforces other habits making them easier to follow. Once you find that habit, it orients the rest of your life around it.

The Philosophy

A keystone habit isn’t necessarily the most important habit from a moral sense. Cycling doesn’t make me a more virtuous person in itself. A keystone habit is the habit with the highest leverage. It creates an identity shift that makes virtuous choices easier by default, not through willpower. In my case because I consider myself a cyclist, my other choices are filtered through the question: “what would a cyclist do?” In my case: eat less dessert, skip the beer, and get a good nights sleep.

A keystone habit doesn’t have to be physical one. It can also be a cognitive one as well.

Marcus Aurelius had a keystone habit of writing in his journal. That habit grounded him in way that had an influence on everything else in his life. How he ruled, the books he read, the people he spent time with, how he treated other people. It was a high leverage habit that helped him be the kind of person he wanted to be.

Seneca had a habit each night of reflecting on his day. He would take stock of what he did well that day and what he could improve. This simple habit of taking time each day became an anchor for finding his weak spots and resolving to do better tomorrow.

Creatures of Habit

So why are good habits such an in important part of of lives?

Because we are creatures of habits. Literally. Humans develop habits so that we don’t have to think through how to do something every time we do it. Think about if you had to consciously manage each step in getting dressed? If we had to give our full attention to each button or zipper, or each time we had to tie our shoes? It would be tiring. Habits save us time and energy.

Think about the first time you learned how to tie your shoes. How much time and effort did that take? It wasn’t easy. But once you got it down, then you could do it without having to really think about it.

Bad habits come about the same way. We often pick them up without thinking about them, only to find that they are much harder to put down. I’ve had plenty of friends who picked up smoking because they hung around friends that were smokers. It was easier just to go along to get along. But years later, when trying to quit, they routinely complained about how hard it was, wishing they have never started.

Your eating habits were probably shaped by the household you grew up in. As a child you really didn’t have a choice in what food was available in your house. But those choices influenced you and created habits that you probably carried into adulthood.

Until we become aware of our habits and interrogate them, we can run on autopilot. If the habit is helpful it can lead to great results and happier life. The habits that don’t serve us, can keep us stuck, holding us back from reaching our highest potential.

Excellence is a Habit

There’s a quote that is often misattributed to Aristotle, which goes:

“We are what we repeatedly do. Excellence, then, is not an act but a habit.”

And I admit that I have misattributed as well on this podcast. It’s actually from Will Durant, the author of The Story of Philosophy, as a commentary on Aristotle’s Nicomachean Ethics. When researching quotes for this episode, I found the whole passage from the book and it’s well worth reading the whole thing:

“Excellence is an art won by training and habituation: we do not act rightly because we have virtue or excellence, but we rather have these because we have acted rightly; "these virtues are formed in man by his doing the actions"; we are what we repeatedly do. Excellence, then, is not an act but a habit.” — Will Durant (commentary on Aristotle in inner quotes)

Think about that. We don’t act because we have virtue or excellence. We act and then develop virtue and excellence. Most people have it backwards. They think you need to be motivated to do the right thing. Aristotle claimed it’s the other way around.

Musonius Rufus

One of the most under appreciated Stoics is Gaius Musonius Rufus, a prominent Stoic philosopher in the 1st century AD, and mentor to Epictetus. Like many of the great philosophers of his day, we don’t know a lot about him because we have very little of his writings. But the writings and references we have about him are of a disciplined and principled man, who taught more about ethics than logic or physics. He was also a farmer who believed that physical labor was essential to building good character.

Musonius believed that the greatest impediment to living a moral life were prejudices we carry from childhood. He saw philosophy as the mental art of healing, and that our actions are indicators of our mental well-being. He taught that right action was more important than discussion. As he put it:

“Practice is more important than theory... because it more effectively leads humans to action than theory does.” — Musonius Rufus

For him, it didn’t matter what you knew, or what you said, but what you did.

Your Habits Control You

One of the key aspects of Stoicism is the dichotomy of control. This is where we clear understanding of what we can control and what we can’t. Habits are a way that we give up some control to make things easier. We end up with behaviors that we’re often barely aware of that control many aspects of our lives. Since we’re driven by habits, it’s important that we choose the habits that drive our lives.

Musonius Rufus recognized that we often err not because we don’t understand the right action, but that we act out of habit:

“So in the majority of other things, we address circumstances not in accordance with the right assumptions, but mostly by following wretched habit.” — Musonius Rufus

Even 2000 years ago, he saw that our habits were incredibly influential on the actions that we take. Bad habits can overcome good intentions.

We might have keystone habits that are detrimental to our lives. People who are addicted to drugs or alcohol have turned something that might have helped them cope in the short-term into something that controls their live. They have a negative keystone habit because everything in their lives revolves around it.

We can also have negative mental keystone habits. Have you ever been around someone that complains all the time? They are not fun to be around. They find something in everything to complain about. Or if you’ve been around someone who is constantly playing the victim. Everything is out to get them and make their lives miserable.

In each case, they’ve let this become the organizing principle of their lives. A good keystone habit is something that gives you the leverage to make a greater impact on all areas of your life.

The Practice

So how do you find your keystone habit?

There are really two kinds of keystone habits. The first is what I have with cycling — a physical habit that becomes an identity. You don't just do the thing, you become someone who does the thing. Once you're "a cyclist," your diet, your sleep, the time at the gym, are not separate disciplines you have to white-knuckle through anymore. They're just what a cyclist does. The identity does the work that willpower used to have to do.

The second kind is a practice that becomes a lens. For me, that's this podcast. Recording an episode every week doesn't just produce content. It changes what I read, because I'm always on the lookout for ideas for the next episode. It keeps me journaling, because half my ideas start as a scribbled note. It's made me pay closer attention to my own reactions, because I need real examples, not just theory. The podcast isn't one habit sitting next to my other habits. It's the thing that organizes them.

Neither of these worked because I decided to "be more disciplined." That's the trap most people fall into. They treat the keystone habit like one more item on the self-improvement list. Musonius would call that following wretched habit toward pleasure instead of virtue. What actually worked is that both of these were fully within my control. I can't control becoming disciplined. I can control whether I get on the bike Saturday morning.

Here's how you find yours.

First: list your habits. Write them all down, no editing, both good and bad. Just get them on paper.

Second: look for the one that touches the others. See where they’re connected. For each habit, ask what else it makes easier, or harder. You're looking for the one habit that shows up in three or more of those answers. That's your candidate.

Third: test it against the dichotomy of control. Is this an action, or is it a mood you're waiting on to arrive? "Ride 20 minutes before work" passes the test. "Be the kind of person who exercises" doesn't. If your candidate fails this test, keep digging. You haven't found the real keystone yet, you've found a wish.

Once you've got it, don't overbuild it. Start looking at ways that you can strengthen that habit. See how you can make it a little more central to your life. Use that leverage to impact the rest of your life.

Conclusion

A good keystone habit is an organizing force of your life. It marshals your energy into something that weaves its way into other areas of your life. Often the side benefits may surprise you.

When I got divorced, I found that cycling was therapeutic. My time on the bike was relaxing, even when I was pushing hard up a hill. It was a space that was all my own where I could let my mind wander on things that were troubling me. It was my zen place. Even today, when I’m feeling stressed or anxious, chewing up some miles in the saddle it a powerful way to reset my mood.

Here's the thing about a keystone habit — it isn’t really about the habit.

The bike doesn't care if I ride it. The microphone doesn't care if I record. What they give me is a door — one small, controllable action that, done consistently, reorganizes everything behind it. Musonius said we act ourselves into virtue, not the other way around. A keystone habit is just that idea made practical. You don't wait to become disciplined. You do the one thing, and the discipline follows.

So don't go looking for the perfect habit. Go looking for the one door you can actually open tomorrow morning. Everything else will start walking through it on its 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.

When was the last time that you read a book. A serious book. Something stretched your mind? Something that you had to stop and go back and reread a sentence or paragraph to make sure you understood it? Maybe even learned some new words? New ideas? In this episode, let’s talk about why you should read deeper — not just so you can check another book off your list, but as a tool to help you deal with the complexities of life.

“Friends, the school of a philosopher is a hospital. When you leave, you should have suffered, not enjoyed yourself.” — Epictetus

The Problem

Last year, only 60% of Americans read at least one book. Almost 57% of Americans placed a bet. That's not a statistic I'm making up to be dramatic. It's from a piece in The Atlantic by Rose Horowitch called "The End of Reading Is Here." She's not calling us illiterate. She's calling us something worse, in a way — post-literate. Still surrounded by words. Words everywhere. Just losing the capacity, and the appetite, to sit with the hard ones.

The top selling books today are simpler and less complex, with young adult novels taking the lead, even among adults. Libraries are following this trend getting easier to read books for patrons. In 1958 the English translation of Doctor Zhivago was the best selling book. Boris Pastenak wrote in long complex sentences, demanding your attention. Last years top novel? Sunrise on the Reaping, the latest in the Hunger Games series. Nothing wrong with that book, but nobody's calling it a wrestling match.

I want to be clear about something before I go further: this isn't me being a snob about it. This isn't "kids these days" or "nobody reads anymore, sad." This is me pointing out something specific — we are choosing, at scale, to stop training the one muscle that everything else in a thinking life depends on. And I don't think that's a coincidence that it's happening at the exact moment we need that muscle most.

Difficult reading, as Maryanne Wolf, a cognitive neuroscientist at UCLA points out, strengthens the cognitive abilities of comprehension and synthesis—the ability to read something and integrate it into real life situations.

And here's why it matters. When you stop reading hard things, you don't just read less. You lose practice at friction. At hitting a sentence you don't understand and going back over it instead of scrolling past it. At holding two conflicting ideas in your head at once instead of picking a side in the first four words. You start expecting to be handed the conclusion. Told what to feel. And when real life doesn't hand you the conclusion, when it just hands you the mess and expects you to work it out, you're out of practice for the one skill that job requires.

Why is Reading Hard?

Reading and writing is not something that comes naturally to us as humans. Our brains don’t naturally have a space set aside for processing the written word. This is a skill that we have developed as humans. Writing allowed us to preserve ideas that otherwise would have been handed down orally, and changed in each telling.

But in that development we’ve also developed logic, grammar, rationality, mathematics, emotional complexity. In order to put something down on paper, the author has to think through their arguments and clearly articulate what they are actually trying to say, so they can best communicate their ideas to the reader.

On the reader’s side, it means that the arguments and ideas don’t disappear as they do when a conversation or video ends. It’s still there on the page, allowing you to go back and dive deeper, consider other possibilities, find rebuttals, and poke holes the flaws you might find.

Reading doesn’t just give you information. The act of reading literally changes the way that you think. Reading helps you construct mental models in a way that no other medium can.

Reading also places you in the mind of other people. It’s like you experience the world as another person. You read their thoughts and observations. You understand a completely different perspective on that world that you otherwise couldn’t. If you only stick to books that are easy, or ones that speak to your worldview, then you never understand how others experience the world.

As we become a more oral and visual world, thanks to social media, we lose something. Social media, while at times can be instructional, is meant to be entertaining and hook your attention, not to deeply educate you. It’s too short for the reader (or watcher) to really engage in the material, to challenge their own thinking. It’s simplified down to soundbites and that’s not a way to educate yourself. If it doesn’t catch your attention, you skim past it looking for something to amuse rather than inform.

Videos are a more passive form of engagement, requiring less imagination and reasoning. In a study by University of California San Francisco, they found that reading actually increases the size of the cortex in the brain. Those that spent more time reading performed better on cognitive tests. Those that spent more time watching videos actually had regions of the brain decrease and performed worse on the same cognitive tests.

This weakens our ability to handle the complexities of the world, other people, and even ourselves. We reduce things down to simple narratives and assumptions. Things become more black and white, eliminating the shades of gray and nuance that are part of the complex world we live in.

The Thinking Class

A few months ago, I listened to an interview with Brené Brown where she noticed an interesting disconnect. She talked about how in her work that she meets with leaders from all kinds of companies, including some of the top tech firms. Every leader she talks to tells the people under them to learn to code, learn data science, get the technical skill that'll survive the future. Yet, when pressed on the books that they read that actually shaped them the most, they all mentioned books on philosophy, critical thinking, literature, psychology, history, even art. None of them pointed to a technical book.

That's not hypocrisy. That's a class system, and it's an honest one, whether anyone means it that way or not. One class gets trained to execute, the other gets to keep the skill of deciding what's worth executing in the first place.

And the interesting things is that a YouGov study on reading in America backs this up. They found that that just 19% of Americans read 82% of the books.

So the question is, which class do you want to be in?

If you’re not expanding your mind, if you’re not challenging yourself to consider alternate viewpoints and new ideas, then you’re making that choice.

When we meet challenges in our lives we can either lower the bar, or increase our capacity. Lowering the bar is easier. Increasing your capacity is harder. But which one has a higher likelihood of being successful?

Attention

What this comes down to is not only are we losing our ability to think about complex things, we’re losing our ability to pay attention. SAT and ACT scores have been falling each year as students struggle with long reading passages, even as the test creators have been shortening the passages for reading comprehension.

College students, even in Ivy League schools, regularly complain about having to read long books for their classes. Not just because they are difficult, but because they struggle with the capacity to finish reading them. Teachers are being instructed to use shorter passages from the books, basically dumbing down the curriculum.

Margaret Rennix, Harvard’s assistant director for humanities and social-sciences support, even talked about how some students see reading as a burdensome way to acquire knowledge.

Think about that. Isn’t that what higher education is about? Increasing your capacity and skills? Challenging yourself so that you’re better, smarter, more creative than when you started?

If we as a society aren’t even just keeping up, but are actively lowering the bar, how do we expect to continue advancing, not just technologically, or as a society, but as human beings?

As Neil Postman wrote in his book, Amusing Ourselves to Death:

"When a population becomes distracted by trivia, when cultural life is redefined as a perpetual round of entertainments... a nation finds itself at risk; a culture-death is a clear possibility." — Neil Postman

The Philosophy

Here's the thing the Stoics understood about the mind two thousand years before anyone ran an fMRI study on it: attention isn't a background feature. It's the kernel of the operating system.

They had a word for it, prosoche, which is usually translated as attention, but it’s really closer to vigilance — a trained, sustained watchfulness over your own mind. They treated it as the foundational discipline. Not a nice-to-have next to the "real" Stoic work. It’s the foundation everything else stands on. Because before you can sort what's in your control from what isn't, before you can choose a response instead of reacting, you have to actually be there long enough to see the choice in front of you. No attention, no discipline. No discipline, no Stoicism.

Epictetus points this out directly:

"When you relax your attention for a while, do not fancy you will recover it whenever you please; but remember this, that because of your fault of today your affairs must necessarily be in a worse condition in future occasions." — Epictetus

So when I say we're losing the ability to sit with a hard sentence, I'm not being precious about literature. I'm saying we're losing the raw material the whole practice runs on. You cannot examine an impression you scrolled past.

Seneca saw his own century's version of this. Not video, not doomscrolling. For him it was people bouncing from scroll to scroll, author to author, never landing anywhere long enough to actually digest it. He wrote to his friend Lucilius:

"You must linger among a limited number of master-thinkers, and digest their works, if you would derive ideas which shall win firm hold in your mind." — Seneca

Linger. Digest. Firm hold. He's not telling Lucilius to read more. He's telling him to read deeper, on fewer things, or end up, in his word, "unsteady." Swap "authors and books of every sort" for "tabs and feeds and fifteen-second clips" and he's describing your Tuesday.

Here's where people get it backwards: they hear "read hard books" and assume it's about sounding smart. It's not. It's about training the exact muscle Stoic practice needs to function at all — staying with something uncomfortable long enough to actually think, instead of reaching for the next hit of easy resolution. Lose that muscle, and you haven't just gotten less well-read, you've lost the capacity for the thing you're actually here trying to practice.

The Practice

So what do you actually do with this. Three things, and none of them require a syllabus.

First: pick one book, and finish it before you start another. This is Seneca's actual prescription, not a metaphor. Most of us have four books going at once and finish none of them, which means we never get past the first, easy layer of any of them. Pick one hard book. No new book starts until that one's done. That's the whole rule.

Second: give it twenty minutes before you're allowed to quit. I noticed when doing theater that Shakespeare was always a challenge for me at first. But about fifteen, twenty minutes in, something shifts. The rhythm starts to land. The jokes start landing where they're supposed to. It's the same thing that happens learning a language. Most people quit a hard book a few pages in, right before the part where it would've started working on them.

Third: build your capacity for attention, your prosoche: take a difficult paragraph from a book you’re reading and really read it. Then read it again. Then, out loud or on paper, explain what it's actually arguing, not what it's about. "This is about grief" is a summary. "He's arguing that grief is the tax we pay for having loved something specific, not something in general" is the argument. That gap between noticing the topic and naming the claim is where the attention actually gets built. Do that once a day and in a month you'll notice you're doing it automatically with things that aren't books. Conversations. Arguments online. Your own thoughts.

None of this is about becoming a more impressive person at dinner parties. It's building the capacity that lets you tell the difference between what's really happening and what you're being told is happening. Conclusion

When I was a child my mother read to me and my siblings every night. Not just when it was convenient. Not when she felt like it. Every night. Even if it was late, we’d read a short book. We had weekly trips to the library which were just as exciting as going to the playground. We even had a Christmas tradition of reading a chapter a night of The Best Christmas Pageant Ever each December.

I passed along that reading habit to my own kids, reading such treasures as Goodnight Opus, The Stinky Cheeseman, and Cowboy and Octopus before tucking them into bed each night. Taking them to the library or Powell’s books each weekend. If they wanted a book, I’d get it for them.

Reading has always been a constant in my life. I always had an extra book in my backpack throughout school, and regularly hit up the used book store when I was in college. When I moved to Amsterdam, I sold and gave away hundreds of books, which I now kind of regret, as I’m slowly rebuilding my library after moving back to Portland.

So I would implore you read some hard books. Not just about philosophy, but other ideas. For me some hard books that changed my worldview include James Carse’s Finite and Infinite Games, Carlo Rovelli’s the Arrow of Time, and Douglas Hofstader’s Gödel, Escher, Bach. The first two aren’t that long but are can shift your perspective in a chapter. The latter, I’ll admit is thick and takes work to get through, but the mental payoff is worth it.

And the thing is, we don’t just have to spend all our time reading books on philosophy, history, or science.  Reading can be educational and entertaining. There are plenty of other books that are complex and challenging that are also entertaining. Personally, I love reading complex science fiction. Works from Asimov, Neil Stephenson, Ursula Le Guin, and Andy Weir have have complex plots, and novel ideas that have changed the way I think. Each one created a world that I conjured in my own imagination, with the help of the author, experiencing things that I never would have considered on my own.

Lastly, reading is fun. You don’t have to read only complex books. You can read something just because it delights you. I remember reading The Hitchhiker’s Guide the Galaxy and laughing my ass off. Every now and then I pick up a Christopher Moore book because I find them ridiculously entertaining. But try to have some veggies with your dessert.

The point is, reading is a muscle that will weaken over time, so make sure you get your reps in.

But read those hard books to so that you can be part of the thinking class, not the part that follows them. Prosoche, vigilance of mind, is how you buy your way into the first group. Not money. Not credentials. Just the willingness to sit with something difficult long enough to actually see it.

As Epictetus put it:

“We should discipline ourselves in small things, and from there progress to things of greater value.” —Epictetus

So, which one are you training for? I know which camp I’m in. See you at the library.

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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Jon Brooks is the host of the Stoic Handbook podcast and Substack page. In this episode we talk about the dangers of over-managing your emotions and finding ways to be a good Stoic while not shutting yourself off emotionally.

You can find out more about Jon and his work at stoichandbook.co

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

Find out more at https://stoic.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.