Podcast Summary: The Daily Stoic

Episode: "Failure Doesn’t Define You—Neither Does Success | Always The Same"

Host: Ryan Holiday
Date: November 10, 2025

Overview: Main Theme and Purpose

This episode explores the Stoic perspective that neither failure nor success should define a person. Ryan Holiday weaves historical anecdotes with philosophical ideas, emphasizing that external circumstances—whether lows like poverty or highs like power—are ultimately transient and do not determine one's character or worth. He further reflects on the enduring sameness of human experience, drawing from both Stoic texts and more recent cultural references to remind listeners of our place within the greater flow of history.

Key Discussion Points and Insights

1. Ulysses S. Grant: A Stoic Example of Indifference to Circumstance

• [00:05–03:09]

  • Story of Ulysses S. Grant falling on hard times after military service, selling firewood to support his family.

  • When recognized and questioned by Simon Buckner, Grant replied, "I am solving the problem of poverty," underlining his acceptance and lack of shame in honest work.

    "Grant knew what the Stoics knew: that outside circumstances don’t say anything about us at all." — Ryan Holiday [00:44]

  • Grant did not let disgrace or menial work define him, nor did he later allow great successes (General of the Union Army, President) to overinflate his sense of self.

  • Parallel to Stoic belief, as described by Epictetus and Marcus Aurelius:

    "As Marcus Aurelius commanded himself: we must accept it without arrogance and let it go with indifference." — Ryan Holiday [02:25]

2. Stoic Reflection: "Always the Same"

• [05:14–09:35]
  • Ryan reads from Marcus Aurelius’ Meditations 4:32, focusing on how human lives, across generations, are fundamentally similar in their desires, struggles, and daily routines.
    • Birth, death, love, conflict, ambition, and disappointment are recurring patterns.
  • References Ernest Hemingway’s The Sun Also Rises and its Bible epigraph:

    "One generation passeth and another generation cometh, but the earth abideth forever."

  • Observes that regardless of technological or societal change, people are engaged with the same basic concerns as their ancestors.

    "What’s left are people. Living, dying, loving, fighting, crying and laughing." — Ryan Holiday [06:50]

  • Historical cycling of arguments and ambitions:
    • Example: Gun control debates in Tombstone, Arizona in the 1880s compared to modern times.

    "Same sticker I have on the, you know, front of the painted porch, but in the 1880s, that’s what the gunfight at the O.K. Corral was about. ... People were fighting and arguing about the exact same thing." — Ryan Holiday [08:42]

3. Humbling and Comforting Wisdom of Stoicism

• [09:35–11:25]
  • The persistence of human nature is at once daunting and comforting:

    "What’s so beautiful and reassuring, but also humbling about Stoic philosophy is these reminders that not that much has changed..." — Ryan Holiday [09:36]

  • Personal reflection: Ryan notes taking the same kinds of notes in Marcus Aurelius’ Meditations as he did years before, underlining the timeless relevance.
    • Draws a line from himself to historical figures also reading and annotating Stoic works.

Notable Quotes & Memorable Moments

• On Honest Work:

  "Grant was feeding his family. He was doing honest work. What was so bad about that?"
  — Ryan Holiday [01:47]

• On Stoic Indifference:

  "We must accept it without arrogance and let it go with indifference. Like Grant, [Marcus Aurelius] saw that success and failure were meaningless. They were impostures. A rock thrown in the air gains nothing by going up, he said, and nothing by falling down."
  — Ryan Holiday [02:28]

• On the Repetition of History:

  "People are people, and they've always been doing the same things. ... Time, as Matthew McConaughey's character says in True Detective, quoting Nietzsche, time is a flat circle."
  — Ryan Holiday [09:40]

• On the Living Tradition:

  "Maybe you have Seneca on your nightstand, just as Jefferson had Seneca on his nightstand when he died. Just as, you know, Cato died holding the copy of Socrates. ... It's a timeless tradition we’re a part of, both intentionally and unintentionally."
  — Ryan Holiday [10:48]

Timestamps for Important Segments

• 00:05 — Introduction to episode theme: circumstances don’t define you
• 00:27 — Ulysses S. Grant story and Stoic lesson
• 02:10 — Relation to Marcus Aurelius’s teaching on indifference
• 05:14 — Reflection: "Always the Same," reading from Meditations
• 06:45 — Discussion of historical continuity and Hemingway quote
• 08:20 — Modern parallels: Tombstone anecdote, gun debate
• 09:36 — The philosophical comfort and humility of sameness
• 10:48 — Tradition: connecting oneself to past Stoics

Tone and Approach

Ryan Holiday’s tone is contemplative, insightful, and gently conversational. He illustrates the ancient wisdom through vivid stories, modern parallels, and self-reflection, creating an atmosphere that is both motivational and grounding—true to the spirit of Stoic philosophy.

Takeaway

This episode urges listeners to internalize the Stoic lesson that neither failure nor success is a true measure of oneself. Our lives—no matter the era—are echoes of the same human experience. What matters is the character that we foster, not the fleeting highs or lows we encounter.