Dying Every Day (Stoic Meditations)

So what do you do when life feels like too much?

Two philosophers give very different answers, and together they point to something you can actually do tonight.

Kierkegaard and Epictetus can help us see which demands belong to the situation, which ones we’ve added ourselves, and what’s still worth doing when we can’t do everything. [...]

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Think for a moment about something you want.

Not something you need.

Something you want.

Perhaps more money. More recognition. A little more comfort.

Now imagine getting it.

How long before it simply becomes normal? [...]

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We’re often told to question everything, seek the truth, and know ourselves. But how much questioning is useful? Is truth always good for us? And can we acknowledge our limitations without becoming bitter about them?

My friend Brandon Tumblin from The Strong Stoic returns for a conversation prompted by passages from Dostoevsky’s novels, using Julian Baggini’s How to Think Like a Philosopher as our starting point. We explore the difference between Stoic acceptance and the resentment of the Underground Man, whether being limited means being flawed, and why admitting we might be wrong can make room for growth.

The conversation moves from doubt and decision-making to the uncomfortable work of self-knowledge. Through The Truman Show, The Matrix, and an imagined workplace feedback exercise, we ask whether learning the truth always helps—and how much depends on our readiness to hear it.

We also consider the limits of language, the mystery of friendship, and the parts of ourselves that other people see more clearly than we do. We close by exploring how envy and certainty can push people apart, and how humility and curiosity might help us reconnect.

A question to carry with you: Where could a little less certainty make room for a better question? [...]

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When does reading help us change, and when does it become a way to postpone the next step?

In this Dying Daily meditation, Thomas à Kempis and Epictetus help us examine the distance between understanding an idea and living it. Reading can clarify what a situation asks of us. But it cannot make the choice for us. [...]

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You can end a busy day having focused intensely on things you would never have chosen as the center of your life.

The messages were answered. The small dispute got another hour. The person you meant to call has gone to bed.

Now the day’s accomplishments look different beside what they displaced.

This is a different problem from distraction. [...]

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Memento mori is a way to bring the important things back into the present. Through Montaigne and Seneca, this episode explores how remembering mortality can loosen our attachment to approval, interrupt postponement, and make room for a more deliberate life.

A simple evening practice: name what you are glad you did, notice what you regret delaying, and make one small repair.

Dying Every Day: practical philosophy for a finite life. [...]

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A message arrives with fewer words than you expected. You read it again. The brevity begins to sound like irritation; the irritation becomes a judgment about your relationship. By the time you put the phone down, you are responding to a conversation that has not happened.

We live among events and our interpretations of them. The interpretations help us navigate. They also become increasingly difficult to distinguish from what we actually observed.

Epictetus makes a demanding claim about that relationship. [...]

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Welcome back to Dying Every Day. This is Day 158.

You’ve read the advice. You’ve asked the people you trust. And you’re still looking.

Somewhere along the way, the search for information became a search for assurance. One asks the world a question. The other asks the world for a promise.

So how much do you need to know before you act? You’ll never know enough to be certain. But you can know enough to act with care. An oracle once called Socrates the wisest man alive. He spent years trying to prove it wrong. [...]

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Welcome back to Dying Every Day. This is Daying Daily.

You have been avoiding this thought.

Not consciously. Not with deliberate effort.

Simply by staying busy enough that it never quite surfaces. By treating awareness of death as something to manage—acknowledged briefly when unavoidable, then returned to its proper place at the far edge of consciousness, well away from the ordinary business of the day.

We have even developed extraordinary technology to support this avoidance.

The busyness, the noise, the endless scroll—all of it serves, among other things, to keep the biggest fact about human existence just below the level of genuine awareness. The Stoics thought this was exactly backward. [...]

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Welcome back to Dying Every Day. This is Mortal Questions.

I want to try something new here on Dying Every Day. I’m calling it Mortal Questions.

The idea is pretty simple. There are certain questions that seem to follow us through life—questions about happiness and suffering, work and love, ambition and regret, attention and death, and so on. Some have occupied philosophers for thousands of years. Others show up on an ordinary Tuesday afternoon when something goes wrong, and we suddenly realize we have no idea what to do.

And often, they’re the same questions.

Every so often, I want to take one of them and spend some time thinking it through. Sometimes the questions come from listeners. I’ve set up an email address—askamortal@dyingeveryday.com—where you can send whatever you’ve been wrestling with (you can remain anonymous or not). [...]

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Welcome back to Dying Every Day. This is Day 157.

What does it take to become strong enough to carry responsibility well?

In this episode, I speak with writer, coach, and author Shane Trotter about discipline, mentorship, responsibility, and the work of character.

Much of Shane’s work centers on a simple but increasingly important idea: people need more than information. They need formation.

We talk about standards, challenge, physical training, responsibility, and the role parents, teachers, coaches, and mentors play in helping young people develop character, judgment, resilience, and purpose.

We also explore what can happen when adults remove too much difficulty from a young person’s life—and why meaningful struggle, properly understood, can be part of learning how to live well.

Shane Trotter’s Work:

Shane writes Setting the Bar on Substack, where he explores education, parenting, character, discipline, and human development through philosophy, psychology, and practical experience.

His new course, Carry the Fire, is designed to help fathers, coaches, and mentors prepare young men to become capable, responsible adults. The program emphasizes mentorship, meaningful challenge, physical training, self-mastery, reflection, and formation.

The emphasis is not simply on teaching lessons. It is on becoming the kind of person capable of carrying something forward.

Shane is also the author of Setting the Bar: Preparing Our Kids to Thrive in an Era of Distraction, Dependency, and Entitlement, a thoughtful examination of what young people need in order to flourish in an age of distraction, overprotection, and slipping standards.

If you are a parent, teacher, coach, or mentor—or simply someone interested in how character is formed—I highly recommend Shane’s work. [...]

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Welcome back to Dying Every Day. This is Daying Daily.

You have been avoiding this thought.

Not consciously. Not with deliberate effort.

Simply by staying busy enough that it never quite surfaces. By treating awareness of death as something to manage—acknowledged briefly when unavoidable, then returned to its proper place at the far edge of consciousness, well away from the ordinary business of the day.

We have even developed extraordinary technology to support this avoidance.

The busyness, the noise, the endless scroll—all of it serves, among other things, to keep the biggest fact about human existence just below the level of genuine awareness. The Stoics thought this was exactly backward. [...]

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Welcome back to Dying Every Day. This is Letters from a Mortal.

Before we begin, a word about this edition of the podcast.

Letters from a Mortal is meant to be experienced a little differently from the usual podcast episode.

The pace is slower. There is more silence.

These letters are meant to be more of a contemplation and an invitation to step away from the noise at least for a few minutes.

They are written mostly for audio, intended for a time of stillness.

There is nothing you need to memorize.

Nothing you need to accomplish. Simply notice what stays with you. [...]

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Welcome back to Dying Every Day. This is Dying Daily.

Aristotle spent years trying to answer a question that most people never stop to ask. Not what makes people successful. Not what makes them comfortable or admired or free from obvious pain. Something harder and more interesting.

What makes a human life genuinely good?

Not good in someone else’s estimation. Not good according to the prevailing standards of the culture.

Genuinely, deeply, lastingly good—the kind of good that holds up under examination, that you would choose again at the end, that constitutes something worth having been.

His answer was not what most people expect. [...]

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Welcome back to Dying Every Day. This is Day 156.

Imagine a young man with every door open.

He is talented, and he knows it. He could be a scholar—the mind is there. He could be an artist; people have told him so. He could go into business and probably do well, or travel, or fall in love, or devote himself to a cause.

Every path is available to him, and that is precisely the point: they are all still available, all still open, because he has walked down none of them. He keeps them open the way a collector keeps things in their original packaging.

To choose one would be to close the others, and he cannot bear to close anything. So he stands at the center of all his beautiful possibilities, turning slowly, admiring them, committing to nothing.

We know this young man. Many of us have been him. And we live in the age that has perfected him: the age of the open tab, the unchosen life, the endless scroll of options, none of which we select.

We have made a virtue of keeping our options open. [...]

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Welcome back to Dying Every Day. This is Dying Daily.

The philosopher and the athlete are working on the same problem. The athlete knows that wanting to be fast is not the same as being fast.

Between the desire and the capacity lies the only thing that actually closes the gap—the practice, repeated daily, in conditions that are sometimes ideal and more often not. No serious athlete waits to feel motivated.

Motivation is a consequence of practice, not its precondition.

You train. The capacity develops. The desire follows.

The philosopher has the same problem and the same solution.

“First say to yourself what you would be, and then do what you have to do.” — Epictetus, Discourses

Epictetus taught philosophy the way a coach teaches sport.

The point is not the argument. The point is performance, and it happens under the actual conditions of your life. [...]

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Welcome back to Dying Every Day. This is Dying Daily.

Picture a man tied to the mast of his own ship.

He gave the order himself. Bind me here, he told his crew, and whatever I say, however I beg, do not untie me until we’re past. Then he had them fill their own ears with beeswax so they couldn’t hear a thing, but he left his own ears open.

And then the ship sails into the most dangerous stretch of water in the world, where the Sirens sing—a song so beautiful that every sailor who’s ever heard it has steered straight for the rocks to get closer, and died there, surrounded by the bones of everyone who came before. The man at the mast hears it. And it’s worse than he imagined. He strains against the ropes. He screams at his crew to turn the ship, to let him go; he has to get closer—and they can’t hear him, and the ropes hold, and slowly the singing fades behind them, and he survives.

That’s Odysseus. And if you’re anywhere near a movie theatre, you might be aware of Christopher Nolan’s Odyssey in theaters (I saw it a few days ago). For this Dying Daily episode, a shorter and more casual version of the podcast, I want to talk about why the Stoics were interested in this story. [...]

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Welcome back to Dying Every Day. This is Dying Daily.

Picture a man tied to the mast of his own ship.

He gave the order himself. Bind me here, he told his crew, and whatever I say, however I beg, do not untie me until we’re past. Then he had them fill their own ears with beeswax so they couldn’t hear a thing, but he left his own ears open.

And then the ship sails into the most dangerous stretch of water in the world, where the Sirens sing—a song so beautiful that every sailor who’s ever heard it has steered straight for the rocks to get closer, and died there, surrounded by the bones of everyone who came before. The man at the mast hears it. And it’s worse than he imagined. He strains against the ropes. He screams at his crew to turn the ship, to let him go; he has to get closer—and they can’t hear him, and the ropes hold, and slowly the singing fades behind them, and he survives.

That’s Odysseus. And if you’re anywhere near a movie theatre, you might be aware of Christopher Nolan’s Odyssey in theaters (I saw it a few days ago). For this Dying Daily episode, a shorter and more casual version of the podcast, I want to talk about why the Stoics were interested in this story. [...]

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Welcome back to Dying Every Day. This is Day 155.

This week's episode is something a little different. Over the past few months, I've been building an audio course called "Resist and Persist: The Stoic Art of Self-Discipline." And I wanted you to hear the introduction. Mostly because the argument it makes stands on its own, and I think it's the most useful thing I've written this year: that if you've failed at self-discipline and everyone listening to this has, it's probably not a character flaw. It was a sequencing error. You were working on the right problem in the wrong order. [...]

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Welcome back to Dying Every Day. This is Day 154.

“Don’t demand that things happen as you wish, but wish that they happen as they do happen, and you will go on well.”

— Epictetus, Enchiridion

Waiting reveals what the soul believes it deserves.

The delayed reply. The stalled decision. The slow line.

The season of life that will not resolve on your preferred schedule.

Impatience is rarely just about time. More often, it is about control. The mind wants reality to move at the pace of its wishes. When it does not, irritation rises—not only because the thing is delayed but also because the self feels crossed.

Epictetus gives one of the sternest and most liberating pieces of Stoic advice: “Stop demanding that things happen as you wish.” [...]

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