Stoic Coffee Break

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.

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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.

Thanks again for listening!

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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.

Courage, one of the four cardinal virtues of Stoicism, is what I consider the fuel for virtue, and really for living a good life. But what does courage actually look like? Are we born courageous or it it something we can develop? In today’s episode we’re going to dive into what Stoics taught about courage and how it’s backed up by modern science.

What Does It Actually Take to Be Courageous?

"Courage is not simply one of the virtues, but the form of every virtue at the testing point."

—C.S. Lewis

The Problem

When I started this podcast, I was scared. Not just nervous. Scared. I was convinced that at any moment, someone was going to figure out that I didn't belong — that I wasn't qualified enough, smart enough, or interesting enough to be talking about Stoic philosophy to strangers on the internet. Imposter syndrome was ever present. Every episode I recorded in those early days, I'd finish it and think, "That’s probably the one where people are going quit listening."

But here's what I've come to understand after years of doing this work — that feeling wasn't a warning. It was an invitation. An invitation to do something that takes real courage: to show up honestly, even when you don't feel ready.

Today I want to talk about courage. Not the Hollywood version — the battlefield moment, the heroic leap. Real courage. The everyday, grinding, unsexy kind that determines the actual quality of your life.

Researcher Brené Brown has spent twenty years studying this. The other day I was listening to a podcast where she was a guest, and they were talking about what it takes to be courageous. What she found in her research cuts against everything we think we know. Courage, she says, isn't a personality trait. It's not something you have or don't have. It's a collection of four learnable skills. And when I dug into her framework for the first time, I kept stopping because the Stoics had already mapped the same territory two thousand years earlier.

So that's what we're doing today. Brown's four skill sets of courage, paired with the Stoic philosophy that's been teaching the same lessons since before Rome fell. And I'll tell you where each one showed up in my own life, because if it's worth talking about, it's worth being honest about.

Let's get into it.

PHILOSOPHY & PRACTICE

SKILL SET ONE: Rumbling with Vulnerability

Brown's first skill set is what she calls "rumbling with vulnerability." She defines vulnerability as uncertainty, risk, and emotional exposure. And the rumble part matters — it means staying in the discomfort instead of tapping out. Not performing openness. Actually sitting with the hard thing.

Most of us don't do this. We armor up. We get busy, get sarcastic, get certain — anything to avoid the exposed feeling of not knowing, of being seen, of possibly being wrong or hurt or rejected.

Brown's research shows that without this foundational skill, the other three are impossible. You cannot be courageous while armored. The armor has to come off first, because vulnerability is a prerequisite for courage. You can’t be courageous if something doesn’t scare you.

The Stoics called this prosoche — self-examination. The practice of looking honestly at yourself, not to punish yourself, but to see clearly.

Socrates felt this was so important that he said, “An unexamined life is not worth living.”

He would often practice self-questioning, cross-examining his own thinking about something. Once, while on campaign with the Athenian army, he stood still on a beach for 24 hours, lost in deep thought. The other soldiers, curious about what was going on, gathered around keeping vigil. Then as the sun rose, be woke from his trance-like state, said a prayer to the day, then went on as if nothing had happened.

Epictetus pushed his students toward self-examination constantly. And Seneca in his treatise On Anger describes his own nightly practice in first person. He wrote:

“When the light has been removed and my wife has fallen silent, aware of this habit that’s now mine, I examine my entire day and go back over what I’ve done and said, hiding nothing from myself, passing nothing by.”

And then, crucially, he doesn't spiral into self-condemnation. He says:

“For why should I be afraid of any of my mistakes, when I can say: ‘Beware of doing that again, and this time I pardon you.’”

That's the practice. See it clearly. Don't hide from it. Just let it go and do better.

When I started this podcast, the vulnerability wasn't optional. I was putting my voice, my face, my actual beliefs out into the world with no idea if anyone would care. That exposure, was scary. But the harder vulnerability, the one that took more courage, was admitting to myself that I was afraid. That I felt like a fraud. Because as long as I kept that hidden, even from myself, I couldn't do anything about it.

The Stoic practice of self-examination gave me a framework for that. Not "beat yourself up at the end of the day." Look honestly. What did you avoid? What did you do from fear instead of from your values? See it. Correct it. Move on.

Doing so allowed me to see myself not as some sage that knew everything, but a fellow traveler along the road, sharing what I’ve learned. That my experiences, both my successes and my failures, could be of use to others.

Practice: Tonight, before you sleep, spend five minutes doing this. Not a gratitude list. An honest review. Where did you avoid something you knew you should face? Not to shame yourself — to see clearly. That's the beginning of courage.

SKILL SET TWO: Living into Our Values

Brené’s second skill set is living into our values, and to be precise about what those values are. She says most people have vague, aspirational values. Integrity. Honesty. Courage. But vague values don't guide behavior under pressure. She pushes people to get specific: what does integrity actually look like in a hard conversation? What does honesty cost you when it's inconvenient?

That gap between stated values and actual behavior is where courage lives or dies.

The Stoics made this the center of their entire philosophy. Virtue, excellence of character, wasn't an abstract idea or an aspiration. It was how you acted, specifically, when it was hard. Marcus writes in Meditations:

"No random actions, none not based on underlying principles."

Every action either expresses your values or betrays them. There's no neutral ground.

And Marcus knew how easy it is to betray them. He was the most powerful man on Earth. He had every excuse to let himself off the hook. He wrote the Meditations as a daily practice of bringing himself back to his values because he knew that without that discipline, the gap widens without you noticing.

One of the things I committed to early on with this podcast was honesty. Not just talking about Stoic philosophy in the abstract, but being real about where I struggle with it. That meant talking about my failures on air. Not as a performance of humility — that's its own kind of armor. But because the show is built on the premise that this work is hard and real, and pretending otherwise would be a lie. It would go against the actual virtue I’m trying to teach.

That was harder than it sounds. There's a version of a podcast host that looks like they have everything figured out. I knew my audience might be more comfortable if I projected that image. But it would have been a betrayal of what I actually believe, which is that the messy, uncertain, still-figuring-it-out life is the only honest one.

Living into your values means it costs you something. If it doesn't cost you anything, you're not really being tested.

Practice: Name two values that are genuinely yours. Not what sounds good, but what actually guides you at your best. Then find one moment from the past week where you acted against them. That's not dwelling on failure. That's useful information. That's where the work is.

SKILL SET THREE: Braving Trust

Brown's third skill set is braving trust. She breaks trust down into specific, observable behaviors — she has an acronym, BRAVING, that maps it out.

B — Boundaries: Say no when you need to; respect others' no

R — Reliability: Do what you say, consistently, without overpromising

A — Accountability: Own your mistakes, apologize, make amends

V — Vault: Keep confidences — don't share what isn't yours to share

I — Integrity: Choose courage over comfort; what's right over what's easy

N — Non-judgment: Ask for what you need without judgment; others can do the same

G — Generosity: Extend the most generous interpretation of others' intentions

But the core insight is this: trust is not a feeling. It's not something that just happens between people. It's built through consistent, specific actions over time. And it requires courage because trusting someone means accepting that you can be hurt.

Most of us either over-trust, where we hand ourselves over and get burned, or we under-trust, we armor up, and we end up isolated. Neither is courage. Courage is the willingness to be in genuine relationship, with your eyes open, knowing the risk.

The Stoics were deeply committed to this idea, even though we don't always talk about it. They believed that humans are fundamentally social, that we are made for community, for relationship, for mutual care. Marcus returns to this again and again. We are not isolated units managing our own inner states. We are connected to each other, and our obligations to that connection are part of what it means to live well. Justice (dikaiosyne) one of the four cardinal virtues, is entirely about relationships with others. You cannot be fully virtuous alone.

I took two breaks from this podcast. Both times, it was because I needed to deal with personal challenges in my life. And both times, the hardest part wasn't the break itself. It was trusting my audience to still be there when I came back.

That's a hard thing. When you build something with people over years, you feel an obligation to them. And stepping away feels like a breach of that. But here's what I had to learn: sticking around just to please others wasn’t serving them. It was serving my fear of being abandoned. Showing up when I wasn't actually present wasn't trust. It was a transaction. Real trust meant being honest about where I was and trusting that the relationship was strong enough to hold it.

It was. Both times.

Practice: Think of one relationship where trust has eroded — maybe slowly, maybe all at once. Don't start with what the other person did. Start with your own behavior. What specific thing did you do or not do that contributed to that erosion? That's your work.

SKILL SET FOUR: Learning to Rise

Brown's fourth skill set is learning to rise, and she's clear that this doesn't mean bouncing back quickly or pretending the fall didn't hurt. It means owning the full story of what happened. Not the sanitized version, not the victim version, not the "everything happens for a reason" version. The real version. What happened. How it felt. What you contributed to it. And what you're going to do differently.

That's hard. Most of us either grab onto the failure and let it define us, or we rush past it and pretend it didn't happen. Rising means doing neither. It means going through it.

Marcus Aurelius wrote what is probably the most quoted line in all of Stoic philosophy:

"The impediment to action advances action. What stands in the way becomes the way."

People print it on posters and put it on coffee mugs. But what it's actually describing is something brutal and honest — that the obstacle doesn't get removed. You go through it. The going through is the point. The going through is what builds you.

I picked this podcast back up twice. And both times, I had to reckon with the question of whether I was coming back because I had something real to say, or because I felt guilty about quitting. That distinction matters. Rising isn't just resuming. It's understanding what happened, being honest about it, and choosing to move forward from that honesty rather than from fear or ego.

The episodes I've done about my own failures, the relationships I've gotten wrong, the times I've been less than I wanted to be, those are some of the most important things I've made. Not because failure is glorious. It's not. But because the willingness to look at it honestly, to say "this is what I did and this is what it cost me and here's what I learned," that's what makes the philosophy real. That's the difference between reading about Stoicism and actually practicing it.

Practice: Pick one failure you're still carrying. Not a small inconvenience. A real one. The kind that still has weight when you think about it. Write down three things: what happened, what you contributed to it, and one specific thing it taught you. Not a silver lining. An actual lesson you can act on.

Conclusion

Brown's research and Stoicism arrive at the same place through different routes. Courage is not the absence of fear. It is not armor. It is not performing strength while feeling nothing.

It is the willingness to examine yourself honestly. To act from your actual values when it costs you something. To trust, and to be trustworthy, even knowing you can be hurt. And to fall — because you will fall — and to get back up having actually learned something instead of just surviving.

That is what this podcast has been about since the beginning. Not because I figured it all out before I started recording. But because I kept choosing, imperfectly and over and over again, to show up honestly. To rumble with the discomfort. To let the work be real.

That's the invitation this week. Not to be fearless. To be honest. Courage follows honesty. It always does.

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.

Kelly McGinnis has a long and storied career working her way up the corporate ladder to CFO and later President of Thermo Fischer, a Fortune 100 company. In this episode we discuss ideas around what it takes to be good leader, company culture, and stepping out on your own.

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

Find out more at https://stoic.coffee

Watch episodes on YouTube!

Find me on linkedIn, instagram, or threads.

Thanks again for listening!

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.