Jerusalem Demsas on The Dispossessed, Gulliver’s Travels, and Of Boys and Men

Cowen inverts his own format: ‘this time we’re actually going to have a conversation with Tyler.’ Jerusalem Demsas and Tyler Cowen each read Ursula K. Le Guin’s The Dispossessed, Jonathan Swift’s Gulliver’s Travels, and Richard V. Reeves’s Of Boys and Men, then argue about them as equals — Demsas speaks more than Cowen across the conversation, and several of the episode’s sharpest claims are his, not hers.

Key ideas

1. The format is genuinely inverted. Cowen states the conceit outright at the open. This is not Cowen interviewing Demsas about her journalism; it is two readers arguing about three books, with Demsas driving as much of the exchange as Cowen.
2. Demsas and Cowen split on what Le Guin actually endorses. Demsas reads The Dispossessed as an ‘ambiguous utopia’ in which Le Guin still clearly prefers the anarchist planet, Anarres, over the capitalist one, Urras. Cowen disagrees: he thinks Le Guin is not on Anarres’s side at all, and reads the novel as showing that some version of human — for him, specifically male — nature persists underneath any institutional arrangement, communal or capitalist.
3. Cowen reads Gulliver’s Travels as a novel about slavery, not primarily satire. On his telling, every society Gulliver visits enslaves someone, except the ridiculous scientific one at Laputa and Lagado — which Cowen takes as Swift’s backhanded case for tolerating a society of cranks and dreamers over one built on caste. Demsas pushes back: Gulliver dismisses the scientists as pointless within pages, so the reading rests on a part of the book Swift himself treats as minor.
4. Both protagonists are restless travellers who come home with nothing to show for it. Shevek and Gulliver each abandon their families to travel, learn things no one else in their world knows, and return empty-handed and unhappy. Both books share a ‘you never escape your prisons’ theme — freedom from one set of institutions just reveals another, more invisible set.
5. Cowen and Demsas disagree on whether travel is worth it. Cowen argues travel does not make people happier on average — ‘people are happier at home’ — but is worth doing anyway as a distinct, valuable form of knowledge that makes reading and understanding the world afterwards richer. Demsas is sceptical, noting that Shevek’s own decisive insight in the novel comes from a friend who never left home.
6. Reeves’s central empirical claim — for men, many policy elasticities are zero — becomes the episode’s biggest disagreement. Cowen takes this (and Reeves’s book generally) as evidence that men and women are more different than he had assumed, and floats a darker reading: societies that reduce war and channel destructive male instinct elsewhere may simply leave a fixed share of men permanently worse off. Demsas rejects this as biological determinism dressed up as social science, citing the education gap’s disappearance among gay men and cross-national variation in male violence as evidence that incentives and institutions, not fixed nature, are doing the work.
7. Demsas’s sharpest critique of Reeves: he never asks what boys should be taught. Feminism, she argues, did not just remove legal barriers for women — it also transmitted concrete cultural lessons (negotiate your salary, don’t let people interrupt you). Reeves catalogues where boys fall behind but, in her reading, never asks whether boys could be coached the same way; she also finds his signature policy proposal, redshirting boys a year in kindergarten, undeveloped as to its classroom effects.

Content

A conversation with Tyler, not an interview

Cowen opens by naming the inversion directly: ‘This show is called Conversations with Tyler, but this time we’re actually going to have a conversation with Tyler.’ The three books were agreed in advance and both parties come prepared with readings, not just questions. The imbalance this produces is worth flagging for anyone approaching the transcript expecting a normal CWT interview: Demsas talks more, but Cowen — usually confined to the interviewer’s chair — volunteers extended, personal readings of all three books, several of which he says are new to him even on a sixth or seventh pass through Le Guin.

The Dispossessed: an ambiguous utopia, or no utopia at all?

Demsas opens with the standard critical label — Le Guin’s novel as an ‘ambiguous utopia’ — and argues that within that ambiguity, Le Guin still clearly prefers Anarres, the anarchist moon, to Urras, the capitalist planet it broke from two centuries earlier. Cowen disagrees flatly: ‘I don’t think she prefers the communal anarchist world.’ His reading turns on Shevek, the physicist protagonist, whom he calls ‘pretty selfish’ and ‘quite a bit like Gulliver’ — someone who leaves his family because he wants to travel and learn, and who comes back with nothing to show for it. Cowen reads Anarres’s supposedly stateless society as secretly coercive (its syndics do shoot dissidents; a central computer plans everything), and reads Urras’s inequality and permanent low-grade war as the price of the only society in the book that actually works.

The two also split on whether the novel is feminist. Cowen notes that when Shevek reaches Urras he sexually assaults a woman who had befriended him, and reads this as evidence against any ‘blank slate’ theory: nothing about growing up on the more gender-egalitarian Anarres inoculated him. Demsas counters that the assault is not evidence of fixed human nature but of Shevek absorbing Urras’s own norms within weeks of arrival — the incentives of the society he is in, not some substrate beneath both societies, produced the act. She also raises a reading Cowen had not considered: that the novel’s most damning material — the boys’ prison games on Anarres, turning tyrannical almost instantly — may be a comment on ‘male nature’ specifically, not human nature generally. Cowen accepts the distinction.

Both agree the book leans on a recurring ‘prisons’ image: Anarres has almost no physical walls, yet Shevek discovers invisible ones everywhere he goes, and neither planet escapes them. They close this thread on a lighter note comparing the novel’s near-total absence of contemporary heirs — Cowen observes that science fiction has shifted overwhelmingly toward dystopia, which he ties to a broader loss of the cultural self-confidence that once let writers imagine, unembarrassed, that reason and technology would simply make things better (his example: 1960s cartoons promising flying cars).

Gulliver’s Travels: satire, or a novel about slavery?

Demsas found the book more readable than expected but is unsure how much a satire this specific can survive four centuries of lost context; she prefers Swift’s short, unambiguous satirical essays (A Modest Proposal) to the novel’s length. Cowen offers his own developed reading instead, arrived at only on his sixth or seventh pass: that Gulliver’s Travels is, underneath the satire, a novel about slavery. Every society Gulliver visits enslaves someone — the Lilliputians enslave him; the Brobdingnagians put him to work as an entertainer; the Houyhnhnms enslave the Yahoos and threaten to enslave or kill Gulliver himself. Only the ridiculous scientific society at Laputa and Lagado — full of impractical projects, unreadable machine-generated books, and what Cowen half-jokingly calls proto-venture-capitalists — has no slavery at all. His reading: Swift is not endorsing the scientists, but suggesting that a society of cranks chasing dreams beats one built on caste.

Demsas is not persuaded: Gulliver spends barely any time with the scientists and dismisses their endeavours as directionless within pages, which she thinks undercuts a reading resting so much weight on that one episode. The two agree, though, that Gulliver himself is hard to read as either simply smart or simply likeable — he survives by doing nothing (waiting, not provoking, exercising patience with captors), yet every time he has agency he chooses another voyage, abandoning a wife and children he ultimately finds too human, too un-horse-like, to bear. They also connect Swift’s ‘faction’ obsession — the Lilliputian war over which end of an egg to crack — directly to 2023: Cowen calls it ‘very 2023, or at least 2021’ and reads Swift as arguing faction is permanent and inevitable, not a modern pathology, a reading Demsas accepts. Cowen adds biographical colour from Swift’s letters to Stella (his likely lover) and his own Irish background — Swift, who called Britain’s treatment of Ireland outright slavery, emerges as sceptical of moral progress but not without hope for it.

Two travellers who come home empty-handed

Cowen draws the two protagonists together explicitly: both Shevek and Gulliver are the only people in their worlds who know things nobody else knows, both abandon family to get that knowledge, and both come home with nothing usable — Shevek’s scientific breakthrough is never shown working in the novel; Gulliver returns disgusted by his own wife. Cowen extends the parallel to the authors themselves: both Swift and Le Guin’s fictional stand-in were, in different ways, abandoned by a parent early in childhood, and both books are obsessed with the question of who the ‘we’ really is.

Does travel make you happier — or just wiser?

The travel discussion becomes one of the episode’s more pointed disagreements. Cowen’s position: ‘Not on average. Some people, it clearly makes happier… but on average, people are happier at home. I strongly believe this.’ He argues most of travel’s value is anticipation and memory rather than the experience itself, yet still urges people to travel because it changes what you can understand afterwards — his example is a 2019 trip to Kyiv that made subsequent reporting on the war legible to him in a way it otherwise would not have been. Demsas questions the premise on two fronts: first, that most people travel badly, staying within their existing social circle and learning little; second, that Shevek’s decisive insight in the novel comes not from his own travel but from a friend who stayed home and simply watched their society fail from the inside. She also floats a more cynical read of the cultural push to travel — that people report themselves happier from travelling partly because they have discharged a social obligation, not because the travel itself delivered anything.

Of Boys and Men: biology, institutions, or both?

Cowen states his headline takeaway from Reeves plainly: ‘it’s simply that for men, a lot of elasticities are zero’ — his example is a free-college programme in Kalamazoo, Michigan, that moved women’s enrolment sharply and men’s not at all. He reads this, combined with the rest of the book, as evidence that men and women are more different, at the margin, than he had previously thought, and connects it back to Le Guin: Urras, the war-prone, male-dominated capitalist planet, is also the only one that ‘works’ in the novel, which leads him to float that a society that reduces war may simply leave a subset of men — those less suited to peace — permanently behind, and that this may be the more honest cost of moral progress than Reeves’s comparatively anodyne policy fixes (paid paternal leave, more male teachers, redshirting boys a year in kindergarten).

Demsas rejects the biological framing directly. She points to research Reeves himself flags but underplays — the education gap closes for gay men — and to cross-national variation in male violence as evidence that institutions and incentives, not a fixed male nature, explain most of the pattern; ‘incentives matter a lot.’ Her deeper objection is that Reeves never applies to boys the lesson feminism has spent decades teaching girls: that underperformance can be cultural, and culture can be coached. Women are routinely told to negotiate salaries and not let themselves be interrupted — concrete, transmissible lessons. Reeves catalogues boys falling behind in reading and classroom engagement but, on her reading, never asks whether boys could be taught the equivalent. She also finds his flagship policy idea, redshirting boys a year, thin: the book does not examine what a classroom of 14-year-old boys alongside 13-year-old girls would actually do to either group’s outcomes.

Moral progress, feminisation, and looking outward

Closing, Cowen offers a provocative synthesis: that moral progress may in large part be the ‘feminisation’ Mill anticipated — as women gained a greater (if still unequal) share of influence, societies became less inclined to fight, a change birth control has likely made permanent. Demsas resists any single-cause or totalising account: she ties moral progress to economic development more than to gender alone, arguing that egalitarian ideas persist because societies organised around them out-compete those that are not. Both then note, more lightly, an asymmetry in policy borrowing: Singapore and New Zealand policymakers routinely ask what other countries do; America rarely does, whether at the federal or the state level, and Demsas suggests the underlying cause may be structural — America has only two neighbours, unlike the tightly packed nation-states that make cross-border comparison a reflex elsewhere.

See also

• Jerusalem Demsas — guest; formerly of Vox, now a staff writer at The Atlantic
• Tyler Cowen — host