They Will Shove This In Your Face

Summary

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The Daily Stoic Podcast: "They Will Shove This In Your Face"

Host: Ryan Holiday
Guest: James Romm (historian, author of Dying Every Day: Seneca at the Court of Nero and Plato and the Tyrant)
Date: June 3, 2026

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Episode Overview

This episode centers on the insidious nature of moral compromise, especially when dealing with powerful but corrupt figures. Drawing from ancient examples such as Seneca’s fraught relationship with Emperor Nero and Plato’s dealings with Dionysius II, author Ryan Holiday explores how small concessions to questionable leaders can spiral into profound betrayals of personal integrity. Scholar James Romm joins to further unpack these historical precedents, reflecting on how the need for access and influence tempts respected figures into complicity. The dialogue connects these timeless lessons to modern leadership, ethics, and the ever-present pull between ideals and ambition.

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Key Discussion Points

1. Seneca's Moral Compromise Under Nero

• Ryan Holiday introduces the topic by recounting how Seneca, exiled and eager to return to influence, compromised his principles to advise Nero.
  • [00:00-01:40]
  • “He had to compromise from the start, Seneca had no love for emperors. But Nero was his way back from exile, his chance to be at the center of things once again, having been unjustly exiled by Claudius in 41 AD.” (Ryan Holiday, 00:11)
• Over time, the small concessions Seneca made snowballed:
  • He witnessed and participated in Nero’s moral excesses, including the murder of Nero’s mother and public humiliations.
  • Seneca’s initial pragmatism devolved into humiliation—a “precedent” for further compromise.
    • “Moral compromise is never a single act. It creates a precedent. Then another and another.” (Ryan Holiday, 01:45)

2. Historical Parallels: Plato and Tyrants

• James Romm notes that Plato found himself in a similar situation, hoping to influence Dionysius II for the better but being forced into ethically murky waters.
  • [05:12-06:33]
  • “The philosopher has ideal notions of what politics is about as a republic … and then when you hit the ground … things don’t work out so neatly for Seneca.” (James Romm, 06:33)
• Both Seneca and Plato illustrate how good men can become trapped, not instantly but “step by step” (Ryan Holiday, 01:55).

3. Philosopher as "Doer" vs. "Talker"

• Holiday and Romm discuss the temptation for philosophers and intellectuals to get involved in politics or leadership, only to lose themselves amidst practical realities.
  • “Maybe this is what leads Seneca astray too, is he wants to be in the room where it happens and loses his bearings as to when one should leave the room where it’s happening.” (Ryan Holiday, 05:12)
  • The challenge: At what point does engagement for the greater good turn into enabling or abetting wrongdoing?
  • “It’s a fine line, I guess, between wanting to be a doer and not just a talker. And then when is your ego leading you into a bad place?” (Ryan Holiday, 05:20)

4. The Slippery Slope of Moral Concessions

• A core insight is the idea that initial compromises (however small) set a precedent, inviting more egregious betrayals.
  • Holiday shares a quote from Pompey:
    • Notable Quote:
      • “Whoever makes his journey to a tyrant’s court becomes his slave, although he went there a free man.” (Pompey quoting Sophocles, Ryan Holiday, 05:55)
• Even with good intentions, proximity to power exposes individuals to gradual ethical erosion.

5. Access vs. Integrity

• “It’s this tension between access and integrity … I gotta preserve my access even though I’m slowly compromising my integrity. That’s the tension. And obviously they all failed that test at some level.” (Ryan Holiday, 08:36)
• Romm points out that in antiquity, a respected philosopher’s presence lent legitimacy to the ruler, something rare today.
  • “A philosopher who’s widely respected … has automatic access because the ruler needs that legitimacy. … We have lost that.” (James Romm, 08:53, 09:21)

6. Ego, Self-Deception, and Leaving Power

• Romm and Holiday highlight how ego and self-deception keep thinkers entangled with corrupt authorities long after they should have walked away.
  • “For Plato to have gone back to the court of Dionysius II a second time, five years after departing in a terrible debacle … That is really. It’s another stunning example of self-deception.” (James Romm, 10:17)
  • “The mental gymnastics that humans are capable of will never cease to surprise you.” (Ryan Holiday, 10:42)
• They discuss the manipulation skills of the powerful, who instinctively know how to keep trusted advisors from defecting, always “shoving the compromise in your face” to maintain control.

7. Personal Application and Modern Parallels

• Holiday reflects on the relevance to modern business and politics (mentioning American Apparel’s collapse).
  • “James Rahm’s book … opened my eyes to some of my own moral compromises, and it changed me. I’ve thought about his book many times in the years since.” (Ryan Holiday, 02:23)
  • They note how ego-driven loyalty, fear of losing proximity, and even just the inertia of habit can prevent people from standing up or walking away—even when the waters are clearly poisoned.

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Notable Quotes & Memorable Moments

• On compromise and precedent:
  • “Moral compromise is never a single act. It creates a precedent. Then another and another.” (Ryan Holiday, 01:45)
• On the allure and danger of power:
  • “It’s a fine line … between wanting to be a doer and not just a talker. And then when is your ego leading you into a bad place?” (Ryan Holiday, 05:20)
• On proximity to tyrants:
  • “Whoever makes his journey to a tyrant’s court becomes his slave, although he went there a free man.” (Pompey quoting Sophocles, Ryan Holiday, 05:55)
• On the philosopher’s role in society:
  • “A philosopher … has automatic access because the ruler needs that legitimacy … We have lost that.” (James Romm, 09:21)
• On human self-deception:
  • “The mental gymnastics that humans are capable of will never cease to surprise you.” (Ryan Holiday, 10:42)

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Important Segment Timestamps

• Seneca’s compromises and humiliation — [00:00-03:00]
• Comparing Seneca and Plato’s ethical struggles — [05:12-06:57]
• Pompey’s warning about tyrants — [05:55]
• The tension of access and integrity — [08:36-09:24]
• Self-deception and returning to power — [10:17-12:01]
• Seneca’s imagined attempts to confront Nero — [12:01-13:27]

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Summary

This episode delivers a potent meditation on the dangers of slowly eroding one’s principles when serving the powerful. Drawing on striking ancient case studies, Ryan Holiday and James Romm paint a picture of how easy it is—even for the wise and well-intentioned—to become complicit. Their dialogue is a timely caution for anyone navigating complex organizations or political life: the cost of “being in the room” can be your integrity itself, lost not in a moment but over a thousand small steps.

Transcript

[Ryan Holiday]

Welcome to the daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world. They will shove this in your face. He had to compromise from the start, Seneca had no love for emperors. But Nero was his way back from exile, his chance to be at the center of things once again, having been unjustly exiled by Claudius in 41 AD. So Seneca swallowed some of his true feelings to advise and to teach Nero. And how did the emperor reward him for this commitment? By shoving the moral compromise in Seneca's face. Constantly. Seneca had to watch as Nero fixed the Olympics so he could award himself the prize. He had to help Nero give a speech. After Nero killed his own mother, he stood aside as members of the ruling class were forced onto the stage, humiliated in performance, even sent into the arena to fight wild beasts. It's a problem as old as time. Just ask Plato, who found himself in the same position with the tyrant in his time. Those that first ask us to bend our principles a little will ultimately return to ask for more and more. They will ultimately require us to contort ourselves into utterly unrecognizable positions. We think we're being pragmatic. In actuality, we're being humiliated. Moral compromise is never a single act. It creates a precedent. Then another and another, as James Rom shows in Dying Every Day Seneca at the Court of Nero. We have some signed copies of the Painted Porch and in Plato and the Tyrant and in his interviews on the Daily Stoic. This is how good men and women end up being trapped. Not all at once, but step by step. And actually, James Rahm's book on Seneca was a book that changed my life. I read it during the sort of Fall of American Apparel, and it opened my eyes to some of my own moral compromises, and it changed me. I've thought about his book many times in the years since. I'm fascinated by the example of Seneca. He's been on the podcast a couple times. He was actually just here in Austin not that long ago, and I asked him about precisely this and we talked about it. A deal. I'm going to bring you a chunk of that episode here for the rest of today's episode. James Romm is great. Do read Plato and the Tyrant and Dying every day and check out his fuller episodes on the Daily Stoic podcast. The Painted Porch, my bookstore here in Bastrop, Texas, has a porch on the back, and it is painted. We actually just repainted it and then we were sort of trying to fix it up a Little bit. It's been sort of an afterthought, but we try to make it a little bit nicer. And we bought some new outdoor furniture. Some chairs, a rug, some string lights, you know, just some stuff that the employees and I myself can hang out on. You know, this is the best time of year in Texas. It's cool and nice. Days are still long, but not so long. Anyways. Where did we get all the furniture? We got it from Wayfair. Outdoor seating, grills, major appliances, storage, patio lights, rugs, decor. Wayfair is your one stop shop for a home. Installation and assembly services are available for a truly seamless experience. Wayfair deals with the hard part so you don't have to. With over 20 million 5 star reviews, you can hear from real customers before you buy. Patio season is here and these deals won't last. Head over to Wayfair.com right now to get your outdoor space ready for way less. W A Y F A I R.com

[James Romm]

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[Ryan Holiday]

One of the things I talk about in stillness is the key is creating some space, right? Time and space for reflection, for talking things through, for thinking about yourself from a little bit of a distance. And therapy can be a great place to do that. And that's where today's sponsor comes in. BetterHelp. Because that time and space is so important for me. I don't want to drive all the way across town for therapy. I don't want to look for parking. I don't want to get stuck in traffic. I just want to be able to talk to someone on the phone or over text. And that's what you can do with BetterHelp. BetterHelp makes it super easy to get started. They match you with a therapist based on your preferences, their own clinical experience. You just do an online quiz, they match you with a therapist. You can switch therapists at any time at no cost. And BetterHelp has over a decade of matching expertise. And you can join 6 million people who have gotten help from BetterHelp. It's a platform you can trust. Just go to betterhelp.com daily stoic to get 10% off your first month of therapy with BetterHelp. Philosophers shouldn't be just writers, they should be doers. And maybe this is what leads Seneca astray too, is he wants to be in the room where it happens and loses his bearings as to when one should leave the room where it's happening.

[James Romm]

Mm, yes, I know that you have the two books there.

[Ryan Holiday]

You can see I took A few notes on this one.

[James Romm]

Yeah. They're very parallel stories.

[Ryan Holiday]

Yes. And it's a fine line, I guess, between wanting to be a doer and not just a talker. And then when is your ego leading you into a bad place?

[James Romm]

That's right. And when do things get so messy that you have to extricate yourself? Seneca tried to extricate himself, but failed.

[Ryan Holiday]

Yes.

[James Romm]

And Plato succeeded, but then had to answer all kinds of questions about what went wrong, why did he bail? And the disaster that he left behind became much worse after his departure. So, yeah, things got very sticky.

[Ryan Holiday]

Well, I have this quote that I think is sort of. It strikes me as maybe the sort of through line of both your books, but I had this on my desk. I don't know when or why I wrote it down, but Pompey's last words, where he quotes Sophocles, he says, whoever makes his journey to a tyrant's court becomes his slave, although he went there a free man. And so you think you're going to do good work for a flawed person, or that you're going to be above the industry that you're working in. Right. Because most of us aren't going to go work for actual emperors or kings. But you think you can go into that place and not get your hands dirty, but you can't.

[James Romm]

Right, Exactly. The philosopher has ideal notions of what politics is about as a republic. I mean, the republic enshrines those ideals in the highest way. And then when you hit the ground. Hit the ground splattering, as it were, things don't work out so neatly for Seneca.

[Ryan Holiday]

It's fascinating to me because obviously Nero doesn't start out as a tyrant. Right. His mother is obviously flawed. And maybe you could have said he could have seen it coming, but with Seneca, it seems much more like a frog in a pot. The heat is slowly being turned up. And then he is in that space where they say it's very hard to see something that your salary depends on you not seeing. And he can't. He can't get out. Yeah.

[James Romm]

Nero started off on a relatively good path. The first five years of his reign were later referred to as the quinquenum neuronis. The best time of the Roman Empire. It wasn't until he became a 20 or he approached his 20s and had the. Actually, no, he was well into his 20s. After five years and more gumption, more autonomy, and took the reins into his own hands more. And then things started to really crash.

[Ryan Holiday]

Yeah. And is it mental illness or is it what Power is it. That power is itself kind of a

[James Romm]

mental illness in his case, very much so. The freedom to do anything, to have whatever pleasures he wanted, to kill his mother or whoever else he wanted, have the Praetorian Guard at his beck and call. Those would drive many human beings into delusions and insanity. And in his case, he was already a little shaky to begin with, so it just sort of exaggerated his natural flaws.

[Ryan Holiday]

It's this tension between access and integrity. And integrity, yes. And I gotta preserve my access even though I'm slowly compromising my integrity. That's the tension. And obviously they all failed that test at some level.

[James Romm]

Yeah. Of course, what's missing from our society, which is present in both Greek and Roman picture, is that a philosopher who's widely respected, as both Plato and Seneca were, has automatic access because the ruler needs that legitimacy. He needs a philosopher, an esteemed philosopher at his court in order to appear to be an enlightened person.

[Ryan Holiday]

Yeah, yeah.

[James Romm]

We have lost that.

[Ryan Holiday]

Also, like, for them, politely declining is not so much an option. Right. The specter of death and real danger, you know, now it's, I don't want to lose my access. It's like, okay, so you don't get reelected and then you go make millions of dollars as a lobbyist or a consultant. Like, you're not. Actually, the downside is so much lower in today's political environment. And so it is much. It's even more about ego than this sort of calculated balance between all the different factors. I think that's the timelessness of the seduction, which is like, over here, I'm saying. And showing you this, and then over here, I'm saying something different. And the human capacity to hear which one of those we want to hear.

[James Romm]

Yeah. And for Plato to have gone back to the court of Dionysius II a second time, five years after departing in a terrible debacle the first time, and having caused a rift in the royal family that resulted in his protege Dion getting exiled. That is really. It's another stunning example of self deception.

[Ryan Holiday]

Yeah. The mental gymnastics that humans are capable of will never cease to surprise you.

[James Romm]

That's right. And Plato says that he devised a test. You know, this is really a testament to his naivete. He devised a test to see whether Dionysius was a suitable student, that he was going to tell him exactly how hard it was going to be to become a philosopher. And probably he had in mind years and years of study, starting with geometry and astronomy and higher math and going up to dialectic. And he was Going to see whether, how he would react. So he lands in Syracuse for the second time, well, the third time, but the second time under Dionysius the Younger and presents him with this scenario. And Dionysius says, oh, well, I already know all this stuff because other people have told it to me. And at that point Plato is sort of done. But the fact that after having lived with him five years earlier for months and months and seeing exactly what kind of person he was, you know, a drunk, a libertine, an unstable emotional figure, that he still thought, well, you know, maybe he'll pass the test and I'll have a true student on my hands.

[Ryan Holiday]

Yeah, I imagine Seneca, you know, he's somewhere in one of his villas and the messenger rushes in, you know, we have news that, you know, Nero's tried to kill his mother and Seneca's grabbing his toga, you know, and rushing over to the palace. I'm going to tell him this time, you know, this has to end. You can't do this. Like, I'm really going to confront him. This is it, you know, it's like we're going to have the come to Jesus conversation, which maybe he literally could have, he could have used that expression, Jesus having overlapped with Seneca, but you know, we're going to have it. And he's walking there, I'm going to confront him, I'm laying on the line, I'm giving him the ultimatum. And then by the end of it, you know, Nero has talked himself out of it, right? And then soon enough he does kill his mother and does crosses the next red line. And crosses the next red line. And the real skill of the Neros, of the, of the tyrants of the trumps, et cetera, is their ability to, to read those people and to know what they have to say to them and what their levers are and how to manipulate them, that at some level they see through them and they, they know how to get them in their pocket.

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