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

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.

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.

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)

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

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.

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.