Stoic Coffee Break

Beating yourself up doesn’t make you better person. Hating yourself doesn’t motivate you more. So what’s the difference between holding yourself high standards and punishing yourself for failure? In this episode we discuss the two warring voices in each of us — the inner critic and the inner coach.

“If you want to improve, be content to be thought foolish and stupid.” ― Epictetus

The Problem

When I was growing up, I used to be incredibly hard on myself. I had this belief that I had to be perfect. Much of this came from growing up Mormon. The standards that I was told that I had to follow were really, for me, unobtainable. I tried so hard to do everything right, be the perfect person, and beat myself up when I thought I had failed. You believe that if you just follow all these rules and act the way you’re supposed to, that you’ll finally be happy. My mom even told me that she was afraid to criticize me about anything because I was already so hard on myself she didn’t want to drag me down even further.

But here’s the thing: you can’t hate yourself into being a better person. Hating yourself might give you some short term motivation and energy, but it doesn’t help you be a happier, thriving person.

The standards that I had handed to me made me miserable.

Because I judged myself so harshly, I also judged others really harshly too. I had this hardline view of how others were supposed to behave. When others made mistakes, rather than being compassionate and kind, I was often as judgmental towards them as I was towards myself.

Another thing that happens when you’re that hard on yourself, is that when others give you feedback or criticism, it always feels like an attack. I felt like it was unfair. I was trying hard wasn’t I? I was doing my best!

But it wasn’t their criticism that was the problem. Because I was already judging myself so harshly, it felt like I was being picked on. Rather than seeing it as correction and feedback, I saw as judgment being piled on what I was dishing out to myself.

So where does that source of this come from?

Shame.

Shame that I wasn’t living up to those standards. Through that perfectionist lens, I saw my failures as a personal reflection of me. Not “I failed at something”, but “I am a failure as a person”. And because of that shame, I couldn’t look at my failures objectively. I looked at them as proof that I was as bad a person as I thought I was. Each mistake was just another item on my checklist as proof that I was not a good person.

In her book, The Gifts of Imperfection, Brené Brown, a well-regarded researcher on shame, puts it perfectly:

“Perfectionism is a self destructive and addictive belief system that fuels this primary thought: If I look perfect, and do everything perfectly, I can avoid or minimize the painful feelings of shame, judgment, and blame.”

Those impossible standards that we hold for ourselves keep us stuck in a spiral because we can’t ever achieve them, then use them as proof that we’re a failure. She puts is simply:

“We cannot grow when we are in shame, and we can't use shame to change ourselves or others.”

The Philosophy

So how do we move past this shaming and harsh self-criticism and become less judgmental about ourselves, without abandoning high standards?

Some people think that Stoicism is about keeping unrealistic standards for ourselves, being unbending and unyielding. Even Marcus Aurelius said, “Be tolerant of others and strict with yourself.” But when he said that, what he meant was that you shouldn’t judge others by the standards you hold for yourself. They may have a different set of values and a different idea of what is important. You shouldn’t expect others to live the way you do.

The Stoics, while they were strict with themselves and trying to live up to their principles, had a clear understanding that humans are fallible. We make mistakes. We screw things up. We’re not automatons. Therefore perfection is impossible.

One of my favorite quotes from Epictetus is:

“The ignorant blame others for their own misfortune. To blame oneself is proof of progress. But the wise see all blame as foolishness.”

But I’ll admit, when I first read this, I didn’t truly understand it. How do you not blame anyone? If something goes wrong, isn’t there someone to blame?

Over time, I started to understand: things happen. Life happens. Nothing will ever work out perfectly.

Then I read a different translation of this quote and it fully clicked:

“Small-minded people habitually reproach others for their own misfortunes. Average people reproach themselves. Those who are dedicated to a life of wisdom understand that the impulse to blame something or someone is foolishness, that there is nothing to be gained in blaming, whether it be others or oneself.”

While it may feel good to blame someone, where does that get you? Rather than worry about who is to blame, accept that it happened, try to understand it as best you can, and get back to work. Sitting in rumination and blame is just a waste of time and energy.

The Virtues

And this is where the four cardinal Stoic virtue comes in.

One of the things that I appreciate about the four virtues (wisdom, courage, justice, and temperance), is that they offer a clear way to of how to treat yourself. When you make a mistake you can use them to look at the situation.

Wisdom is the practice of discernment, to be able to see things for what they are, not the story you’re telling yourself. You remove the judgment, which allows you to see that facts clearly. This gets to the root of what really happened without all the assumptions and self-recrimination. It also allows you to see that you’re not the only person who has ever made this mistake.

Courage helps you to look at a situation and own up to your mistakes. It’s being able to be honest with yourself so that you can take responsibility for your part. Courage means that you’re willing to step up and try and fix things when you have screwed up rather than becoming defensive or avoidant.

Justice is all about fairness. When you’re too hard on yourself, you’re not being fair with yourself. You believe that you’re not worthy because you’re a bad person and deserved to be punished. But justice says the opposite. Justice means that you treat yourself with fairness, kindness, and compassion. It doesn’t mean that you let yourself off the hook, but rather you stop holding yourself to an impossible standard. You accept that you’re human just like the rest of us.

Temperance means that you find that healthy balance between holding impossibly high standards and lowering them to the point where they are meaningless. If your standards are too high from what’s even possible, then you’ll continue down that shame spiral. If they’re too low, then they have no meaning. Standards, meaning the quality of how you do something, are aspirational. You may not always meet them, but you can always strive for them. They should push you to be better, but not so far out of reach they can’t be met.

But I need to make a distinction here: standards are how you do something. Expectations are a hoped for outcome. One you can control, one you can’t. When you fail to meet your standards, you can do something about it. When you expect something to work out a certain way, that’s outside of your control.

The Practice

So how do you move past this? What can you do be better, to hold high standards, and still be kind to yourself?

Most of us have two competing internal voices: the inner critic and the inner coach.

The inner critic operates through shame, fear, and inadequacy. It’s brutal you when you fall short. It says: you’re lazy, you’re weak, you’ll never be good enough. When you actually do perform well, it tells you: you could have done better, it was luck, or you don’t deserve it. The inner critic is effective at producing effort but terrible at producing long term wellbeing or sustainable performance.

The inner coach is clear and honest in its assessment. It’s genuine invested in your growth. It holds you to your standards because it believes in what you’re building and genuinely has your best interest at heart. It says: “Okay, you fell short of your standard. Here’s what really happened and here’s what do to do differently. Now get back to work.” When you perform well, it acknowledges it and builds on it. When you fall short, it’s honest without being cruel. The inner coach is demanding, not punishing.

In his Meditations, Marcus Aurelius often called out his failures in order to live up to his principles. It wasn’t self-flagellation. He wrote to recognize the patterns, note where he fell short, renew his commitments, then got back to work. No spiraling or drama. Just an honest assessment followed up by renewed action.

So let’s talk about what healthy self-criticism looks like because this is where most people get it wrong. There’s a difference between holding yourself accountable and being cruel to yourself. It’s a subtle but important distinction.

Healthy self-criticism looks like this:

Specific: “I didn’t prepare enough” rather than “I’m a failure”

Behavioral: focused on actions rather than identity

Forward looking: asking “what will I do differently?” rather than dwelling on what went wrong

Proportionate: the size of the self-correction matches the size of the actual failure

Brief: it processes the failure and moves on rather than ruminating

Unhealthy self-criticism is the opposite of this. It’s global (“I always do this”), identity-based (“I’m just not disciplined”), backward-looking (“I failed”), disproportionate, and ruminative.

This leads us to create a story that isn’t based on reality, but rather distorted and exaggerated. Because we’re caught in ruminating, we punish ourselves over and over and spiral out.

The Stoics would see unhealthy self-criticism as a failure of discerning impressions: accepting a distorted and exaggerated story as the truth. The Stoic practice is to examine your impressions to see if they are actually true: do you always fail? Do you really have no discipline?

The inner coach helps you see a clear-eyed version of the truth, supported by the facts. It encourages you to take corrective action rather than sitting in rumination. It would tell you the failure here is the harsh judgments you place on yourself, not the failure itself.

The Stoics had a simple practice called the Evening Review that illustrates how you can apply this in your life. Seneca described it in his letters:

“When the light has been taken away and my wife has fallen silent, aware as she is of my habit, I examine my entire day, going through what I have done and said. I conceal nothing from myself, I pass nothing by. I have nothing to fear from my errors when I can say: ‘See that you do not do this anymore. For the moment, I excuse you.’”

We can break this out into three simple questions:

What did I do well today that I want to build on?

Where did I fall short of my standards, and what specifically happened?

What will I do differently tomorrow?

The reason why this is so effective is that it’s simple, honest, and built on encouragement, not punishment.

Conclusion

We’re all going to make mistakes and have failures. It’s part of being human. But every time you let the inner critic take control, you’re doubling the failure — the original event, and the self-punishment afterwards. It’s kicking yourself when you’re already down. The inner coach on the other hand is a wise mentor, there to help you learn from mistakes and turn them into fuel for future growth.

To be clear, this is not letting yourself off the hook. It’s not an excuse or a way to lower your standards. It’s about honest assessment to gain a more realistic view why you failed and how you can take corrective action. The inner coach is encouraging yet demanding and wants you to hold to your standards. But it sees the standards as an aspiration, not as the iron rule.

The next time your inner critic takes the wheel and starts driving you towards the cliff of self-punishment, take a breath and remember, you’re making a judgment, telling a story about what the situation means — and you have the power to change that story.

Call up your inner coach and walk through the situation. Think about how a good friend would talk you through it with a clear eye, kindness, and encouragement. And be that friend to yourself.

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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Jason Stacy is a performance coach and author of The Pressure Code. He works with high performers including world tennis champion Aryan Sabalenka. In this episode we talk about how coming from living on the streets to being a top performance coach. We also discuss his formula of energy, emotions, and environment, and how the right combination of those leads to reaching your highest potential. You can find out more about Jason and his work at thepressurecode.com

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.

So much of our lives are governed by rules that we aren’t even really aware of. Many of them we never even really question because we just assume that’s the way things are. But what if by questioning those rules, we can live with more agency, leading to a life we choose?

“The object of life is not to be on the side of the majority, but to escape finding oneself in the ranks of the insane. “ — Marcus Aurelius

The Problem

I grew up in Salt Lake City, in the Mormon Church. And when I say my life was prescribed, I mean prescribed. Mission. Marriage. Career. Family. In that order, on that schedule. It wasn't a suggestion — it was presented to me as the truth. Not "this is one way to live." This is the way. This is reality.

I followed the path that I thought I as supposed to. I played the part as best I could but always felt like I was just repeating the lines someone else wrote for me. I didn’t feel like I was being authentically me, just the me that everyone else expected I should be.

When I would question things or have experiences that contradicted what I was taught, I was told that I just needed to have more faith. That it was my fault that my belief wasn’t strong enough. So I doubled down, trying to fit myself into a system that didn’t work for me. I tightened the mask, hoping that this time it might finally fit.

What’s interesting in looking back on my time in the church was that tended I gravitated to others that didn’t wear the mask. I envied those that bucked the system and followed their own path. Being around them I found that I could be more of my authentic self. I didn’t have to pretend to be someone that I wasn’t.

And here's the thing about growing up inside something that total — you don't experience it as a rule. You experience it as just how things are. You don't question the water you're swimming in.

The last few years I was in the church, I would attend church infrequently. It was exhausting trying to fit myself into a way of living that was so ill-fitting. I was at odds with the doctrine. Told that obedience to the leadership was more important than anything else. I got tried of “you just have to have more faith” as the answer to questions they couldn’t answer.

I finally reached the point where I asked: is this actually true, or is this just what I was taught?

The day I finally left, I didn't just leave a church. I left a rulebook I'd mistaken for reality itself. It literally felt like a giant weight had been lifted off my shoulders. I felt free.

Once I left, I still had a long journey. Leaving the church, I lost a big part of my identity. I lost a community. I lost a certainty in how I was supposed to be in the world. It took years for me to find my footing and create a life by my choice, not the script that was handed to me.

But here’s something important that I learned, and it’s something that most people will never understand. You are allowed to do exactly what you want in life and be the person you want to be. But it also comes with some caveats:

1. Everyone else is allowed to do the same.

2. You are responsible for your choices and actions.

3. You don’t get to choose the consequences of your actions.

Maybe you didn't grow up Mormon. Maybe you didn't grow up religious at all. But I'd bet you're living inside a version of the same thing right now. A career path you never chose so much as inherited. A way of dressing, or dating, or succeeding, or how you’re supposed to act as a man or a woman, a way of being that you copied because everyone around you was doing it and it looked like law.

Here's the uncomfortable question: how much of what you're doing right now is because it's true — or because it's expected?

We treat these two very different things like they're the same. There's what's actually true — gravity, death, the fact that actions have consequences you don't control. And there's what's agreed upon — how a man is supposed to act, what a "respectable" life looks like, how long you're allowed to be sad before people get uncomfortable. One of those doesn't care what you think. The other is just a bunch of people's habits, dressed up to look like law.

But here’s the thing: when you’re younger you think that adults have it all figured out and that when you grow up, you’ll have it figured out too. But the real truth is this: we’re all just making it up. Most of the “rules” are just conventions. They’re habits that we’ve agreed to as a society. It’s just a game that we’re all playing.

That's the trap. Not that the game exists — because it always will. The trap is forgetting you're allowed to notice you're playing it.

The Philosophy

Epictetus has a way of putting this that cuts through the noise:

"Remember that you are an actor in a play, the character of which is determined by the author... whatever character he gives you, act it naturally. For this is your duty, to act well the part that is given to you; but to select the part, belongs to another." — Epictetus, Enchiridion 17

You don't pick your role. You didn't choose your family, the time you live in, your body, most of your circumstances. That part's not negotiable. That's fate. That's nature.

But here's what people quietly assume, but Epictetus never said: that the script is fixed too. It isn't. How you play the role — that's entirely yours. And most of what we call "the rules" isn't the role. It's just the version of the script the people around us happen to be using.

Why do we follow this script, even when it doesn't fit? Marcus Aurelius gets at the mechanism:

"It is in our power to have no opinion about a thing, and not to be disturbed in our soul; for things themselves have no natural power to form our judgements." — Marcus Aurelius, Meditations, Book 6

The rule doesn't have power over you. Your agreement to it does. Take the agreement back, and the rule is just a suggestion somebody made up.

This isn't just old philosophy. Brené Brown found the same thing studying belonging. She draws the line like this:

"Belonging is being accepted for you. Fitting in is being accepted for being like everyone else. If I get to be me, I belong. If I have to be like you, I fit in." — Brené Brown, Braving the Wilderness

And she says it even sharper in one line:

“the greatest barrier to belonging is fitting in.”  — Brené Brown

Most of what we call "the rules of life" is just scaffolding for fitting-in dressed up as necessity. It isn't.

Now — before this turns into an excuse to blow everything up, remember: you get to choose how you play your role. You do not get to choose what happens when other people react to it. That's still not yours. Dropping a convention doesn't mean the world applauds or changes for you. It might mean people are confused, annoyed, or gone. That's the actual price of the ticket — and it's worth paying, but only if you go in with eyes open.

Practice

Okay. So how do you actually tell the difference between a real rule and a made-up one?

Step one: the nature-or-convention check.

Take something you're currently obeying without question. Ask it one question: does reality enforce this, or does a group of people enforce this?

Gravity doesn't need anyone's cooperation. It just is. "You should have your career figured out by 30" needs everyone around you to agree to it — and enough of them do that it feels like law. It isn't. It's consensus.

Run a few things through it. Death is nature. Grief having a "proper" timeline is convention. Cause and effect is nature. What counts as a "respectable" job is convention. You'll be surprised how much of your daily anxiety is you enforcing a rule that nobody's actually holding a gun to your head about.

Step two: name the fear underneath it.

Once you've spotted a convention you've been treating like gravity, ask: what do I actually think happens if I break this? Say it out loud. Specify it. Not "bad things" but "My mother will be disappointed." "People will think I've failed." "I'll lose my place in the group."

Usually what's underneath isn't catastrophe. It's disapproval. That's real, it costs something — but it's not the same category of thing as danger. Naming it strips the myth off it.

Step three: one deliberate move.

Pick one small, low-stakes convention this week and break it on purpose. Not to be reckless — to notice. Notice that the world doesn't end. Notice that some people react. That reaction belongs to them. It always did.

This isn't about becoming a contrarian for its own sake. It's about finding out, in a small way, which parts of your life are foundational and authentic, and which parts you've just never tested.

Conclusion

Here's what this isn't: it's not permission to burn everything down and call it freedom. You're still in the play. You still have a role — family, work, responsibilities, people who depend on you. None of that goes away. What changes is why you're playing it.

There's a difference between reciting lines someone handed you because you never thought to ask if they were true, and standing in the same spot, saying the same words, because you've actually chosen them. From the outside those two things can look identical. From the inside, they're the whole difference between a life you choose and a performance.

What is this is really about is seeing the game for what it is. It’s understanding the difference between reality and the “rules” that society quietly enforces. Those rules can be bent or even broken.

But remember, you can’t control the consequences. You don't get to control how people respond when you make that shift. Some will be confused. Some will be hurt. Some will leave. That was never yours to manage, and it never is. That's the price, and it's worth paying, because the alternative is spending your one life optimizing for a game you never actually agreed to play.

So this week, find a rule. Ask if it's real. And if it's not…maybe it’s time to break it.

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

Find out more at https://stoic.coffee

Watch episodes on YouTube!

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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.

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!

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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.