We Are All Trying This | Train To Let Go Of What's Not Yours

Summary

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The Daily Stoic - Episode Summary

Episode: We Are All Trying This | Train To Let Go Of What's Not Yours
Date: November 24, 2025
Host: Ryan Holiday

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Overview: Main Theme and Purpose

This episode of The Daily Stoic explores two central Stoic concepts:

1. The universality of personal struggle, even among those considered wise or accomplished (as exemplified by Seneca’s correspondence with Lucilius)
2. The necessity of training oneself to let go of attachment to people and things, recognizing their ephemeral nature (drawing on the teachings of Epictetus and supported by personal anecdotes).

Ryan Holiday delivers a reflection on these themes using Stoic texts and relatable, modern analogies, aiming to foster humility, appreciation, and resilience amid life's inevitable changes and losses.

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Key Discussion Points & Insights

1. Stoic Teachers Are Fellow Travelers—Not Sages on Pedestals

• Seneca’s Honesty and Humility (00:32–02:39)

  • Ryan discusses how Seneca, despite his vast knowledge and wealth, was open about his own struggles and inconsistencies.
  • When questioned by his friend Lucilius about why he offered advice without having perfected himself, Seneca admits his imperfection and frames himself as a fellow patient:
    • Quote: “I am not such a hypocrite as to offer cures when I am sick myself...I am lying in the same ward as it were, conversing with you about our common ailment and sharing remedies. So listen to me as if I were talking to myself.” (Ryan reading Seneca, 01:30–01:54)
  • Ryan ties this humility to the writings of C.S. Lewis, who described himself as "one amateur to another," emphasizing that advice lands best from those just slightly ahead on the same journey.

• The Daily Stoic’s Approach (02:40–03:02)

  • Ryan frames his own role and that of the podcast similarly:
    • Quote: “None of us are all knowing experts looking down from a pedestal. No, we, like the ancient Stoics, are fellow students half a step ahead, walking the same path, trying our best to learn and grow together.” (02:42–03:02)

2. Letting Go of What’s Not Yours – The Core Practice

• Epictetus’ Guidance and the “Already Broken” Mindset (05:28–06:41)

  • Ryan reads and unpacks a passage from Epictetus (Discourses 3.24): treat everything—possessions and relationships alike—as temporary, not truly belonging to us.
  • The Roman tradition of reminding victorious generals, “Remember, thou art mortal,” is offered as a model:
    • “When there is something we prize or something that we love, we can whisper to ourselves that it is fragile and mortal and not truly ours.” (06:18–06:31)

• The Zen Cup Analogy (07:09–07:38)

  • Ryan introduces the story of a man who says of his cherished cup, “The cup is already broken,” so that its eventual breakage causes less pain.
    • Quote: “And then, of course, when it does break, he’s not surprised. I think this is what Epictetus is saying on a couple of levels.” (07:20–07:31)
  • This mindset is essential when facing both worldly successes and personal attachments.

• Impermanence in Life’s Peaks and Relationships (07:39–09:55)

  • Ryan illustrates impermanence:

    • Successes (bestseller status, careers, youth) are temporary:
      • “Your run on the bestseller list, in my case, eventually it comes to an end. Your time in the NFL comes to an end. Your youth comes to an end. Right? All things come to an end.” (08:18–08:39)
    • People and relationships are also subject to this flux, as highlighted by Scott Galloway’s insight about the stages of a child’s life being fleeting.

  • Profound Reminder:

    • “Our precious One is not a possession. They are a gift that we have temporarily, ephemerally, that we are losing not just day to day, but also permanently, all at once as well, hopefully in a long time. But we cannot say that for certain.” (09:00–09:30)

• Living and Loving with Awareness of Loss (09:56–10:37)

  • The Stoic response isn’t despair, but heightened appreciation and kinder action while we can:
    • “We have to say to ourselves, remember, thou art mortal. We have to say to ourselves, the cup is already broken. It’s already gone. You have it now, but not forever.” (10:18–10:32)
    • The aim is to act before it’s too late, to express love and practice gratitude—knowing nothing is guaranteed.

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Notable Quotes & Memorable Moments

• Seneca’s humility:
  "I am not such a hypocrite as to offer cures when I am sick myself...I am lying in the same ward as it were, conversing with you about our common ailment and sharing remedies. So listen to me as if I were talking to myself."
  — Seneca, via Ryan Holiday (01:30–01:54)

• C.S. Lewis on Shared Struggle:
  "I write as one amateur to another, talking about difficulties I have met or lights I have gained."
  — C.S. Lewis, quoted by Ryan Holiday (02:16–02:24)

• Stoic equality:
  “None of us are all knowing experts looking down from a pedestal. No, we, like the ancient Stoics, are fellow students half a step ahead, walking the same path, trying our best to learn and grow together.”
  — Ryan Holiday (02:42–03:02)

• Fragility of attachment:
  "When there is something we prize or something that we love, we can whisper to ourselves that it is fragile and mortal and not truly ours. No matter how strong or invincible something feels, it never is."
  — Ryan Holiday (06:20–06:31)

• The “already broken” teaching:
  “The cup is already broken. ...and then, of course, when it does break, he's not surprised. I think this is what Epictetus is saying on a couple of levels.”
  — Ryan Holiday (07:20–07:38)

• Impermanence of success and people:
  "Your run on the bestseller list... eventually it comes to an end. Your time in the NFL comes to an end. ...Your youth comes to an end, right? All things come to an end."
  — Ryan Holiday (08:18–08:39)

• Cherish those you love, knowing it's temporary:
  "Our precious One is not a possession. They are a gift...we are losing not just day to day, but also permanently, all at once as well..."
  — Ryan Holiday (09:00–09:30)

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Timestamps for Important Segments

• 00:32–03:12 – Seneca’s humility, the shared struggle of teacher and learner, and C.S. Lewis’s parallel insight
• 05:28–06:41 – Passage from Epictetus on loss and detachment (“remember, thou art mortal”)
• 07:09–07:38 – Zen cup parable: “the cup is already broken”
• 07:39–09:55 – Applied impermanence: success, relationships, and Scott Galloway on the fleetingness of each stage of parenthood
• 09:56–10:37 – The practical Stoic response: practice awareness, avoid entitlement, cherish what you have while you have it

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Tone

Ryan delivers these reflections with humility, warmth, and encouragement, evoking both the comforting reassurance that no one has it all figured out and the gentle urgency of acting with love and presence before change or loss inevitably arrives.

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For listeners:

This episode is an accessible, heartfelt meditation on Stoic attitudes toward impermanence. It's especially resonant for those struggling with attachment, change, or feelings of inadequacy in living up to philosophical ideals. Ryan’s honest anecdotes and classic Stoic texts remind us that wisdom is walking together, not standing above.

Transcript

[Ryan Holiday]

Foreign.

Welcome to the Daily Stoic Podcast where each day we bring you a Stoic inspired meditation designed to help you find strength and insight and wisdom into everyday life. Each one of these episodes is Based on the 2000 year old philosophy that has guided some of history's greatest men and women. Help you learn from them, to follow in their example, and to start your day off with a little dose of courage and discipline and justice and wisdom. For more visit Dailystoic.com. We are all trying this Seneca wasn't perfect. He struggled, as all humans do, with inconsistencies between his philosophy and his actions. He was ungodly wealthy and you know, he worked for Nero. So why should we listen to him? Why did Lucilius, his friend and correspondent.

Take his advice seriously?

As it happened, the two had an exchange about this very issue. Seneca quotes Lucilius writing to him, asking, how is it that you are advising me? Have you already advised yourself? Have you gotten yourself straightened out? And Seneca replies, I am not such a hypocrite as to offer cures when I am sick myself. No, he says, I am lying in the same ward as it were, conversing with you about our common ailment and sharing remedies. So listen to me as if I were talking to myself. I am letting you into my private room, giving myself instructions while you are standing by. Seneca wasn't writing from a sage like place of superiority. No, he was writing as a fellow traveler, someone in the trenches of life wrestling with the same struggles as everyone else. CS Lewis said he wrote for the same reasons. He said, I write for the unlearned about things in which I am unlearned myself. It often happens that two schoolboys can solve difficulties in their work for one another better than the master can. The fellow pupil can help more than the master because he knows less. The difficulty we want him to explain is one he has recently met. The expert met it so long ago that he is forgotten. I write as one amateur to another, talking about difficulties I have met or lights I have gained.

This.

This is the essence of Seneca's letters, Marcus Meditations, and Epictetus discourses. It's also how I hope you read and listen to what I talk about in Daily Stoic. None of us are all knowing experts looking down from a pedestal. No, we, like the ancient Stoics, are fellow students half a step ahead, walking the same path, trying our best to.

Learn and grow together.

Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastow County I drove my car about halfway down the dirt road that we live on, thought, this isn't going to work, stopped, parked it walked the rest of the way home, borrowed my wife's car, drove into Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation, it getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields and on the unpaved roads like the one that I lived in. We got to go deep into the Hill Country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we, I mean not just my wife, but both my kids, who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course, because you never know when you'll end up on a Toyota Adventure Detour. And of course, this is stoicism, too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that. If you've got the resilience and the right companion to make it wherever the road takes you, discover your uncharted territory. Learn [e-mail] Trucks Adventure detours I'm recording this on a Monday, and Monday is our grocery store day in our family. I usually pick my kids up from school and we go over to Whole.

Foods, get all our groceries for the week. Although here very shortly we're going to.

Go over there to get our Thanksgiving turkey because they've got a bunch of great options. Turkeys start at 1.49a pound if you have prime with organic birds at $2.99 a pound and they only carry no antibiotic ever. Turkeys that will bring quality to your table at a great price. Whole Foods has great everyday prices on all your Thanksgiving essentials, whether you celebrate with a massive family or just a few close friends. And everything they sell has high standards to help you shop with confidence. Enjoy. So many ways to save on your.

Thanksgiving spread at Whole Foods Market. Train to let go of what's not yours. This is the November 24 entry in the Daily Stoic. We've got a nice big passage from Epictetus Discourses today. Whenever you experience the pangs of losing something, don't treat it like a part of yourself, but as a breakable glass, so when it falls, you will remember that and won't be troubled. So, too, whenever you kiss your child or sibling or friend, don't layer on top of that the experience of all the things you might wish, but hold them back and stop them. Just as those who might ride behind triumphant generals remind them that they are mortal. In the same way, remind yourself that your precious one isn't one of your possessions, just something given for now, but not forever. That's Epictetus Discourses 324 as it happens. Actually, at a Roman triumph, the majority of the public would have their eyes glued to the victorious general at the front, one of the most coveted spots during Roman times. Only a few would notice the aide in the back, right behind the commander, whispering into his ear, remember, thou art mortal. What a reminder to hear. At the peak of glory and victory in our own lives, we can train to be that whisper. When there is something we prize or something that we love, we can whisper to ourselves that it is fragile and mortal and not truly ours. No matter how strong or invincible something feels, it never is. We must remind ourselves that it can break, can die, can leave us. Loss is one of our deepest fears. Ignorance and pretending don't make things better or stronger. They just mean the loss will be all the more jarring when it occurs. There's a Zen story about Guy who has a beautiful cup. And he says to himself over and over and over again, the cup is already broken. The cup is already broken. The cup is already broken. And then, of course, when it does break, he's not surprised. I think this is what Epictetus is saying on a couple of levels. One, he's just reminding yourself that when you're triumphant, when you're successful, when you're at the top of the world, it never lasts, right? Seneca being a profound example of this. Top of the world, exile. Top of the world, exile. Top of the world. Executed, right? This is how it goes. It doesn't last. It never does. Your run on the bestseller list, in my case, eventually it comes to an end. Your time in the NFL comes to an end. Your time selling real estate in the bull market, it comes to an end. It always does. Your youth comes to an end, right? All things come to an end. And so realizing that this is just.

This thing given to you for now.

And you should enjoy it and be present for it and appreciate it, but never lose sight of the fact that it is already broken, it is already gone. It's already in the process of leaving or falling apart. Entropy is working on it in this very moment. Now, the next part of this, the harder part, is realizing that this isn't just true for status or accomplishment or momentum or whatever, possessions, but also for people. Professor Scott Galloway told me this, and I've written about it before, but he was talking about how you're constantly losing your kids, right? They're a four year old for one day, then they're four year olds in one day. As they are getting older, you are losing who they were, right? They were a baby for so long, a toddler for so long, preteen for so long, a teenager for so long in your house for so long. And most tragically, as Marcus Aurelius feels almost incomprehensibly, you don't get them forever at all, right? Just as they don't get you forever at all. And we have to remind ourselves, as Epictetus says, that our precious One is not a possession. They are a gift that we have temporarily, ephemerally, that we are losing not just day to day, but also permanently, all at once as well, hopefully in a long time. But we cannot say that for certain. And so to take them for granted, to feel entitled to them, to mistreat them, this is a profound sacrilege. And we have to avoid that. And one of the ways we do it is by reminding ourselves of that ephemerality. We have to do this. We have to do it regularly, we have to do it consistently. We have to do it as a practice. We have to say to ourselves, remember, thou art mortal. We have to say to ourselves, the cup is. It's already broken. It's already gone. You have it now, but not forever. Loss is a real fear because it's painful. Grief accompanies it and so many other painful things accompany it, but it is there. And no amount of wishing otherwise makes it not the case, Right? No amount of accomplishment or achievement makes you less mortal. You are mortal, you always have been, and so is everyone and everything you've ever been connected to. So let's live and act and treat people accordingly, and let's do it before it's too late.

Hey, it's Ryan. Thank you for listening to the Daily Stoic podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30, 30 million people have downloaded these episodes in the couple years we've been doing it. It's an honor. Please spread the word, tell people about it. And this isn't to sell anything. I Just wanted to say thank you.

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[Ryan Holiday]

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[Ryan Holiday]

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