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

Summary

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Podcast Summary: The Daily Stoic

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

Host: Ryan Holiday
Date: November 10, 2025

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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.

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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.

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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]

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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

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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.

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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.

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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 Failure doesn't define you, and neither does success. Of course he was disappointed. It had been a long and hard fall. He descended from West Point to second lieutenant during the Mexican American War. But now Ulysses S. Grant was selling firewood by the side of the road. He must have hoped that no one would recognize him in his heart would have sank when Simon Buckner, an old school and war buddy, did. Good God, Grant, he burst. What are you doing? But Grant decided he would not be ashamed. I am solving the problem of poverty, he replied. Grant knew what the Stoics knew that outside circumstances don't say anything about us at all. That it didn't matter, as Epictetus said, what we bear, only how we we bear it. Prant was feeding his family. He was doing honest work.

What was so bad about that?

After all, Cleanthes was a lowly water carrier in Athens and proud of it. Now, had Grant been caught stealing to support his drinking habit, that would have been different. Or if he'd accepted a Confederate commission because the pay was better. Again, that would be different. As I talked about in my episode with Ron Chernow on the Daily Stoke podcast, who wrote of his best biographies about Grant, Grant understood this so called menial work of selling firewood didn't say anything about him. What he cared about was making an honest living and providing for his family. The position didn't define him. And not only was this position temporary, but a few years later he would become general of the Union army and a few years after that President of the United States. And yet again, Grant would refuse to let those high positions define him either. As Marcus Aurelius commanded himself, we must accept it without arrogance and let it go with indifference. Like Grant, he 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. What matters is who we are. What matters is the character we live by.

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[Ryan Holiday]

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Always the same. This is today's entry in the Daily Stoic. Think by way of example on the times of Vespasian and you'll see all these things. Marrying, raising children, falling ill, dying, wars, holiday feasts, commerce, farming, flattering, pretending, suspecting, scheming, praying that others die, grumbling over one's lot, falling in love, amassing fortunes, lusting after office and power. Now that life of theirs is dead and gone. The times of Trajan again the same. Marcus Aurelius, Meditations 4:32. And then the meditation. Ernest Hemingway opens his book the Sun Also Rises with a Bible verse. One generation patheth and another generation cometh, but the earth abideth forever. The sun also rises, and the sun goeth down and resteth to the place where he arose. It was this passage his fascinating editor, Maxwell Perkins, who I urge you to read about. Perhaps Perkins would say that it contained all the wisdom of the ancient world. And what wisdom is that? One of the most striking things about history is just how long human beings have been doing what they do. Though certain attitudes and practices have come and gone, what's left are people. Living, dying, loving, fighting, crying and laughing. Breathless media reports or popular books often perpetuate the belief that we've reached the apex of humanity or that this time things are really different. The irony is that people have believed that for centuries. Strong people have to resist this notion. They know that, with few exceptions, things are the same as they've always been and always will be. You're just like the people who came before you, and you're but a brief stopover until the people just like you who will come after. The Earth abides forever, but we will come and go. And I mean, I think Meditations itself is a remarkable demonstration of this. Probably not accidentally, Right. All the things that Marcus is talking about, complaining about, worrying about, seizing on, are immensely familiar and accessible to all of us. Right? 2,000 years ago, sometime in the year, let's say, 160 AD, Marcus struggles to get out of bed and writes a passage about how he likes to huddle under the blankets and stay warm. Exactly the same, right? You think about the struggles Marcus Aurelius has with Commodus. Maybe that's what you're going through right now. You think of Seneca trying to contain Nero, telling himself, you know, I'm one of the good guys. I'm one of the adults in the room. And you think about how politically people in the Capitol, which is named after Capitoline Hill senators, right? Same position as people like Seneca had, were telling themselves about the current president. Right? The same thing over and over and over and over again. People are people, places are places. I did a meditation on this. We did this road trip, and we stopped in Tombstone, Arizona, which is the site of the gunfight at OK Corral. And what's fascinating is you walk down the streets of Tombstone. This is a place that's burned to the ground, been rebuilt to look historic for the most part. Some of the buildings actually are pretty old. But the point is, these bars, what stickers do they have in the window? The sticker is new. That wasn't a technology in 1880 or whatever, but they got these stickers in the window. What do the stickers say? You can't carry a handgun inside this establishment. Right. 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. It was about whether people could openly carry guns in town. I'm not making a Second Amendment argument here. I'm saying that people were fighting and arguing about the exact same thing. Just as the Earps had moved to Tombstone, Arizona. Why? To make their fortune, to make a name for themselves, to have a better life. The same reason that maybe you're moving to Arizona or Austin or Europe.

Right.

It doesn't matter. People are people, and they've always been doing the same things. And I think what's so beautiful and reassuring but also humbling about Stoic philosophy is these reminders that not that much has changed, that the hardware issues remain the same, the software issues remain the same, despite all the updates and attempts to fix the bugs. So we can calm down a little bit. Right? People are people, places are places. History is the same thing happening over and over and over again. Time, as Matthew McConaughey's character says in True Detective, quoting Nietzsche, time is a flat circle. It's beautiful, As I said, haunting, humbling. All these things at the same time. And it's something we can't lose track of, and it's something we have to think about constantly. And when I hold Meditations, that's what I think of. I've actually got the leather edition right here in my hands. Since I got my first copy of Meditations, I've been going through that one. I have a very worn copy, has lots of notes in it I went through. And I've been rereading it. It's on my nightstand as I've been going through and rereading it. What strikes me most is that I'm still making notes in the same spots about the same things just as other people have been doing for thousands of years. 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. Right. It's a timeless tradition we're a part of, both intentionally and unintentionally. And there's something beautiful and terrifying in that.

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.

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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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