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Ryan Holiday Learns Being A Stoic Is Not As Easy As It Looks

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07.05.2026

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Ryan Holiday Learns Being A Stoic Is Not As Easy As It Looks

The leading proponent of stoicism criticizes Trump and quickly finds it’s hard for him to be, well, stoic.

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Let’s just get this out of the way — I like Ryan Holiday.

In case you’re not aware of who he is, Holiday is a popular author who’s become a popular author by being famous on the internet. Unlike a lot of internet influencers, his chosen domain of expertise is somewhat unusual, however. For more than a decade, he’s been the public face of Stoicism — the ancient Roman philosophy that advocates regulating your emotions and being resilient in the face of external challenges.

Essentially, Holiday has repackaged the words of Marcus Aurelius, Seneca, Epictetus, et al. into various modern contexts, and pitched stoicism as a panacea to the anxieties of the 21st century. There are some problems with the way Holiday’s denatured stoicism to make it palatable for the masses, and let’s be honest, very profitable. Aside from selling millions of books, Holiday is huge on the lucrative corporate lecture circuit. Still, when you survey the landscape of what his fellow self-help gurus are selling, Holiday’s stoic advice, which frequently amounts to telling people to toughen up and not be a slave to their desires, has a much better chance of actually helping people than most.

Beyond that, his huge email lists and popular podcast have become an important vehicle for promoting other authors who write on a wide variety of topics that go well beyond stoicism. Holiday owns a bookstore and is constantly touting books he likes on his YouTube channel, which is also admirable.

Unfortunately, the problem with being the world’s most famous advocate of stoicism is that the world expects you to be, well, stoic. And recent events involving Holiday’s somewhat incongruous advocacy of left-wing politics have revealed that Holiday can definitely let his emotions get the better of him in a very public fashion.

Like I said, I like much of what Holiday does, and I’m not judging him too harshly for this. As a somewhat public figure, I’ve been angry on the internet myself. But what’s happened to Holiday is fairly ironic. If it involved someone else, it might be the kind of thing he himself would characterize as a teachable moment stoicism was made to address.

The proximate cause for Holiday’s bout of internet infamy began just over a week ago, when he posted a short reaction video to Ivanka Trump talking about some of the positive things she had learned from reading Marcus Aurelius’ Meditations. If you watch the video, from the very beginning Holiday is smirking and rolling his eyes, and at one point he literally sticks his tongue out and makes a big thumbs down gesture on the split screen as Ivanka is talking — even though everything she says about Aurelius is uncontroversial and anodyne.

As soon as she’s done talking Holiday renders his judgment. “Here’s the thing: She’s totally right,” he says. “That’s exactly what Marcus Aurelius said. That’s exactly what stoicism is about. She’s just not living or acting in accordance with it in any way. If you did, you’d have an intervention with your dad, whose life would be dyed with his horrible, negative, mean bullying thoughts all the time.” It devolves from there.

I think we can agree that in many very obvious respects Donald Trump has whatever the opposite of a stoic temperament is supposed to be, but how is it a matter of stoicism to necessarily make this his daughter’s problem? Especially when she’s out in public espousing........

© The Federalist