The Real Difference Between Stoics and Cynics | Cynicism Expert Inger Kuin (Pt. 2)

Podcast: The Daily Stoic
Host: Ryan Holiday
Guest: Professor Inger Kuin, University of Virginia
Air Date: November 22, 2025

Episode Overview

In this deep-dive weekend episode, Ryan Holiday interviews Professor Inger Kuin, a leading expert on ancient Cynicism and author of Diogenes: The Rebellious Life and Revolutionary Philosophy of Diogenes the Cynic. Their conversation explores the nuanced differences and overlaps between Stoicism, Cynicism, and Epicureanism, challenging popular misconceptions and revealing the enduring relevance of Diogenes’ radical outlook. Through engaging anecdotes, sharp philosophical contrasts, and thought-provoking analysis, the discussion probes how ancient schools diverged over order, social norms, freedom, and political engagement—even as their concerns often intertwined.

Key Discussion Points & Insights

1. Philosophical and Historical Connections

• Both Stoicism and Cynicism trace lineage to Socrates, with Zeno (Stoic founder) taught by Crates (a Cynic, student of Diogenes).
  • "They are in this bind, right, where they're both wanting to underplay the connection, but they can't completely deny it." — Prof. Kuin (08:49)

Differences in Worldview:

• Stoics: Believe in a divine, rational order to the universe. Human flourishing means living in accordance with this order.
• Cynics: Reject any divine organizing principle; see social conventions and institutions as arbitrary, not sacred or necessary.
  • "For the Cynics, there is no such overarching organizing principle. Right? ... The status quo, the world that we live in, is not necessarily the best of all outcomes." — Prof. Kuin (09:56)
• Stoics and Order: Endorse living in organized societies, including autocracy, because it reflects universal reason.
• Cynics and Anarchy: Social structures are not natural or necessary—anything not rooted in nature is open to radical questioning.

2. Morality, Etiquette, and Social Critique

• Cynics' View: Distinguish sharply between true moral issues (justice) and mere etiquette/convention.
• Diogenes' Provocations: Famous for questioning taboos (e.g., public masturbation), arguing they’re matters of etiquette, not ethics.
  • "Diogenes would say it's a question of etiquette, it's not a moral question. Right, right. Like, moral questions are about justice." — Prof. Kuin (13:30)
• Stoics’ Conservatism: Cautious about over-questioning social systems; fear chaos if conventional order is undermined.
  • "There's a conservatism to Stoicism ... that is not there in Diogenes." — Holiday (12:58)

3. Role of the Outsider and Critic

• Diogenes as Necessary Critic: Exist as an exception enables him to challenge society, but a world full of Diogeneses would risk anarchy.
  • "If we had a society that consisted solely of Diogeneses ... there would be a lack of coherence and constructiveness ... A society without Diogenes is extremely dangerous." — Prof. Kuin (15:04)
• Cynic Critique: Keeps social order honest by continually asking if social structures are truly justified.

4. Freedom through Detachment

• Cynic Independence: True freedom is not relying on external goods (“preparation for poverty”).
  • Diogenes famously tells Alexander the Great, “Get out of my sunlight.”
  • "Because you have boiled down life to its essence ... you are able to be happy with your handful of beans and your stale bread." — Prof. Kuin (17:24)
• Stoic Constraint: More willing to make pragmatic choices, serve in societal roles, and endorse status quo for stability.

5. Resilience, Exposure, and Power

• Diogenes as Resilience Athlete: Practiced living with discomfort to become fearless and free.
  • "He is an athlete in terms of inhabiting the human body and finding out what it's capable of." — Holiday (24:11)
• Stoicism and Cynicism Shared Values: Both advocate for preparation, resilience, detachment from luxury.
• Power Relations: Diogenes’ self-sufficiency neutralizes worldly power—his independence makes Alexander the Great powerless over him.
  • "Power only exists when you let the other person wield power over you." — Prof. Kuin (25:45)

6. Slavery, Social Hierarchies, and Critique

• Stoic Blind Spots: Stoics internalize their freedom, often fail to critique institutions like slavery, seeing them as social wallpaper.
• Cynic Radicalism: Diogenes directly calls slavery absurd, able to question what Stoics take for granted.
  • "There’s no reason why the status quo should be good. You don’t have to revere it." — Prof. Kuin (28:01)

7. Women and Exclusion

• Inclusion in Philosophy: Cynicism’s rejection of status allows participation by women (e.g., Hipparchia, Krates' wife).
  • "There’s nothing about cynicism that precludes women from participating in it." — Prof. Kuin (32:15)
• Stoicism adopts equality only gradually, as it becomes more institutionalized and elite-focused.

8. Evolution, Institutionalization, and Elite Capture

• As Stoicism gets absorbed by Roman elites, it loses critical edge.
  • "As Stoicism becomes institutionalized ... the Stoics start to become people who have much more to lose." — Prof. Kuin (29:51)
• Outsiders (Cynics/Epicureans) keep questioning the insiders.

9. Language, Misunderstanding, and the “Cynic” Word

• The word "cynic" suffers most in modern usage—originally positive, now negative.
  • "All three words have really suffered, but perhaps cynic, the worst ... it's almost exclusively a negative word, cynic with the lowercase c." — Prof. Kuin (40:47)
• Invention of lowercase “cynic” links to Rousseau; true Cynicism is idealistic, not nihilistic.
  • "Diogenes thinks that it is possible to be a good person and to live a good life." — Prof. Kuin (44:05)

10. Anecdotes, Quotes, and Philosophical Zingers

Notable Anecdotes:

• Diogenes "begging a statue"—practicing being rejected (23:47).
• Diogenes’ response to philosophical puzzles—direct, performative rebuttals (48:13).
• The famous encounter: Alexander the Great asks Diogenes if he can do anything for him; Diogenes replies, "Yes, stand out of my sunlight."

Notable Quotes:

• "I'm practicing being rejected." — Diogenes anecdote, Holiday paraphrasing (23:57)
• "Between the Stoics and the Cynics, they have only a shirt between them." — Roman poet Juvenal, quoted by Holiday (19:09)
• "If you are no longer communicating with people who are on the outside, then you’ve lost that opportunity." — Prof. Kuin (31:14)
• "Whoever goes to the court of a tyrant becomes his slave, even if he goes there a free man." — Soft (attributed by Holiday quoting Pompey's last words, 64:45)

Notable Segment Timestamps

• 07:29–15:31: Core differences and similarities between Stoicism and Cynicism; societal order, nature, and questioning social norms.
• 15:31–18:10: Diogenes as outsider; the need for critics in society.
• 23:44–25:15: Begging a statue: resilience and exposure therapy as philosophy.
• 26:57–28:32: Slavery, justice, and radical critique.
• 32:15–34:13: Gender, class, and who gets to philosophize.
• 40:47–46:21: Modern misuse of “cynic”; how language changes philosophical reputations.
• 48:13–50:56: Socratic method vs. Diogenes’ immediacy; intellectual honesty.

Further Reading & Recommendations (54:39 and onward)

• On Diogenes: Penguin edition by Robin Hard; How to Say No (Princeton series)
• On American Cynicism: Ambrose Bierce, The Devil’s Dictionary, “Occurrence at Owl Creek Bridge,” and “Parker Adderson, Philosopher”
• On Modern Stoicism: James Stockdale, Viktor Frankl

Memorable Moments

• Holiday on Rousseau: “He’s a shitty person. ... He’s not ashamed about being a shitty person.” (42:34)
• Society’s need for questioning: “Society needs the sort of freaks and hippies and artists and weirdos who question everything … and then there’s the bucket, the handful of things that it actually turns out the reasons are pretty spurious.” — Holiday (28:32)
• On Socrates vs. Diogenes: “In a way ... there’s something kind of intellectually dishonest about the Socratic method ... There’s something refreshing about Diogenes, who just says what he means in a clever, straightforward way from the jump.” — Holiday (49:13)

Conclusion

This lively and insightful episode not only clarifies what sets Cynics and Stoics apart but highlights how essential radical critics like Diogenes are to any society. It challenges listeners to see philosophy not as an abstract exercise but as a lived, courageous commitment to truth, resilience, and freedom. If you want to test your ideas—and not just accept the world as it is—there’s no better place to start.