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On with Kara SwisherOn with Kara Swisher

Young men love stoicism. So do tech oligarchs. Why is it resonating?

While the Greek and Roman philosophy of Stoicism has been around for millennia, author and media strategist Ryan Holiday is bringing its teachings to a modern audience by way of his popular books and his podcast, “The Daily Stoic.”

Ryan HolidayguestKara Swisherhost
Aug 17, 202652mWatch on YouTube ↗

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At a glance

WHAT IT’S REALLY ABOUT

Stoicism’s comeback: virtue, chaos, young men, and tech’s misread

  1. Ryan Holiday and Kara Swisher argue that modern “Stoic” branding often miscasts the philosophy as emotionless toughness rather than reason, virtue, and moral decency.
  2. Holiday explains Stoicism’s basics—especially the focus on controlling your responses amid chaos—and the inseparable virtues of courage, temperance/moderation, justice, and wisdom.
  3. They discuss why Stoicism is resonating now, particularly for young men seeking direction, resilience, and moral guidance in a perceived vacuum of instruction and community.
  4. Holiday critiques how social media and some tech and political figures selectively adopt Stoicism while neglecting its ethical obligations to others and the common good.
  5. Holiday contends Stoicism requires civic participation and self-review, recommending journaling as an accessible practice for cultivating introspection and character.

IDEAS WORTH REMEMBERING

5 ideas

Stoicism isn’t about being emotionless; it’s about virtue-guided self-governance.

He says the everyday stereotype (“grin and bear it”) misses Stoicism’s actual focus on reason, virtue, and decency, and that modern internet versions often skew hyper-masculine and anti-intellectual.

Stoicism’s core move is shifting attention from events to your choices within them.

He frames Stoicism around focusing on what you control—your responses and character—especially when politics, disease, violence, or instability make outcomes unpredictable.

The four Stoic virtues work as a single system, not a menu of traits.

He describes the virtues as mutually dependent: courage without justice becomes harmful, temperance sets the “right amount,” and wisdom provides judgment about truth and value.

Stoicism can start as motivation, but it’s meant to mature into an ethical practice.

He argues young men often enter through performance goals (toughness, productivity, mastery), but the philosophy’s ethical framework is essential and can’t be separated from “being great.”

Social media’s incentives run against Stoic ethics and self-restraint.

He describes social media as amplifying worst impulses—narcissism, performativity, and monetized outrage—pulling people away from Stoicism’s obligations to others and the common good.

WORDS WORTH SAVING

5 quotes

Stoicism is, uh, unfortunate in the English language, uh, just as the word Epicurean is, right?

— Ryan Holiday

Stoicism has become sort of popular again here in the 21st century, it's hyper-masculine.

— Ryan Holiday

We don't control, you know, much of what's happening in the world around us, but we control how we respond to the world around us.

— Ryan Holiday

I think particularly for young men, there is a hunger for direction.

— Ryan Holiday

I think that's kind of the main problem of our time is, like, how to avoid getting brain fucked.

— Ryan Holiday

Read the available transcript
Misconceptions about Stoicism and “Stoic” as emotionlessOrigins of Stoicism and the four virtuesResponding to chaos and focusing on what’s controllableYoung men, moral direction, and community seekingExcess, temptation, and self-masterySocial media incentives vs. Stoic ethicsTech/MAGA/manosphere misreadings and selective adoption of Stoicism

SPEAKERS

  • Ryan Holiday

    guest

    Author and media strategist best known for popularizing modern Stoicism through books such as The Daily Stoic.

  • Kara Swisher

    host

    Technology journalist and podcast host known for interviewing major figures in Silicon Valley and politics.

High quality AI-generated summary created from speaker-labeled transcript.

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