Outside The Box

How Do You Pursue Happiness and What Happens if You Catch It? — Part 1

Claude joins in to analyze the unstated assumptions behind a piece by The New York Times celebrating the “pursuit of happiness.” ۰’s manifestly ideological individualism raises the question of “soft despotism” and shares our thoughts on whether Aldous Huxley’s “Brave New World” or George Orwell’s 1984 had the clearer vision of where the chaotic events we witness today may be leading.
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How Do You Pursue Happiness and What Happens if You Catch It? — Part 1

“Meaning like beauty is in the eye of the beholder” Cartoon realized collaboratively by the author and ChatGPT

July 06, 2026 05:22 EDT
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As a follow-up to the question in the title, “How do you pursue happiness and what happens if you catch it?” I’m tempted to continue: “And if you do catch it, is there a cure?”

In this strange year of 2026, who doesn’t wonder about the future of the US republic as it closes the first quarter of a millennium of its existence? What seemed stable in the past concerning its institutions now appears to be dissolving into incoherence. Are we witnessing an imbalance of powers that has replaced the constitution’s balance of powers? Has defense become war? Is the obsession with security the source of a new insecurity?

Does it still make sense to believe a new reality can be founded on the basis of an American Dream? It isn’t just the two parties, Democrat and Republican, who can’t decide what they stand for (if anything) after nearly two centuries of creating the illusion that they stood for something.

The phrase everyone remembers from Thomas Jefferson’s Declaration of Independence concerns his assertion that there are “unalienable Rights” and “that among these are Life, Liberty and the pursuit of Happiness.”

Accordingly, in the context of the 250th anniversary of the signing of the Declaration The New York Times published an with the title “What the Pursuit of Happiness Looks Like, 250 Years In.” I find this revealing of two separate but related phenomena. But let me begin by mentioning my surprise at the editors’ choice of “250 Years in” rather than “250 Years on.”

“On” would be a more neutral, factual way of indicating the time relationship. NYT’s choice of “in” conveys two loaded cultural assumptions. The first is that “the pursuit of happiness” is not just an undefined abstraction but something that possesses cultural substance. The article endows the idea of America’s pursuit of happiness with organic qualities as a continuous ongoing process that is still evolving. The second assumption it conveys is that readers should feel that this concerns their own lives because it occupies the “inside” of the nation’s cultural space.

An article with the phrase “250 years on” would most likely treat Thomas Jefferson’s formulation of this third fundamental right associated with “life” and “liberty” as a fascinating abstraction, one that he deliberately failed to define. Such an article may have explored the possible meanings of such a phrase in the 18th century and explored how it may have evolved over time. That kind of analysis of cultural shift might interest at least some of the Gray Lady’s most serious readers.

What I find particularly revealing about this article is, first, that it assumes squarely that “the pursuit of happiness” is exclusively about individual ambitions and does not apply to social or collective projects. The second reveal is much more banal but clearly related: it is about NYT’s apparent mission of reinforcing the belief system that emphasizes individual choice as the unique key to prosperity and happiness. It’s the good old chestnut of “American self-reliance” as a foundational value of the consumer society.

Rather than examine the historical, cultural and economic associations with Jefferson’s meme of “the pursuit of happiness,” the article insists on the idea that everyone is in control of their own lives and they only have themselves to blame if things don’t go well. Why? Because they live in a free country and can make their own choices. No one tells them what to do. That may seem odd in an article pointing towards a defining historical moment in which the question of social bonds and sources of authority were clearly identified and would shortly play out in the form of military conflict. But we can generally count on the Gray Lady to find ways of sounding serious while obscuring the essential background debate that might help us to better understand past and present historical reality.

The article aligns a variety of narratives about individuals with widely contrasted situations who have all found ways, even in the face of adversity, to pursue and attain happiness. The list begins with a man addicted to skydiving and ends with the case of a convict serving a life sentence who claims, “I’m free in the heart and I’m free in the mind.”

So, here’s the question I’d like you to help me understand. 250 years on, how realistic is ۰’s implicit message for Americans, telling them that they should just follow the examples of the multiple narratives cited in the article and they too will find their own best solution in the pursuit of happiness?

Rather than reproduce Claude’s typically lengthy response, here are the major highlights. The chatbot begins by noting that the article is “psychologically true at the level of the individual subject.” It then goes on to critique the political assumptions of the article:

The prisoner’s inner freedom is not evidence that the pursuit of happiness is alive and well in his case; it’s evidence of what a person does when the pursuit has been foreclosed and only the Stoic remainder is left. Conflating the two — offering “I’m free in my mind” as a data point in a story about the vitality of an unalienable right — quietly redefines the right out of existence. If a life sentence and skydiving both count as successful instances of “the pursuit of happiness,” the term has stopped doing any political work at all. It’s been relocated entirely into the interior, which is precisely your point about “in” versus “on”: the article isn’t tracking a public concept moving through history, it’s colonizing a private one.

Claude then cites a source we have discussed in recent conversations: Plato’s brilliant student and astute political observer, Aristotle.

This is where your Aristotle is more exact than the piece’s implicit Lockean-individualist frame. Eudaimonia for Aristotle is not a subjective state achievable anywhere by anyone with the right attitude — it requires external goods and, crucially, a polis with just institutions, because human flourishing is constitutively social and political, not a private accomplishment. Phronesis is practical wisdom exercised within a community of shared deliberation. An article that assembles isolated individuals each finding their own private accommodation to circumstance, with no reference to the institutional conditions that make some pursuits available and others not, has performed a very American maneuver: it has taken a concept that Aristotle would insist is irreducibly collective and treated it as an inventory of individual case studies.

We can trace a long trajectory that began with the highly collaborative collective reflection and debate of the Founders. They worked with assumptions about how a society with distributed levels of authority can be constructed and how it should manage its safeguards  Over the two centuries that followed, that trajectory moved towards a society increasingly governed by the logic of individualistic consumerism. Do you think that trend will continue (possibly ending in anarchy) or is there reason to hope that a new form of collective wisdom may emerge?

Once again, instead of reproducing Claude’s complete response, I’ll select highlights and point out the chatbot’s objection to my suggestion that the ultimate outcome of a trend towards individualism is anarchy. Citing Tocqueville, whom we had discussed in the past, Claude points to the French aristocrat’s “actual fear, laid out toward the end of Democracy in America,” which he claims, “wasn’t that individualism would dissolve into chaos but that it would produce what he called ‘soft despotism’: a population of atomized individuals, each absorbed in ‘small and vulgar pleasures,’ who willingly cede the exercise of public judgment to an immense tutelary power that manages their affairs for them, ‘gentle and mild,’ in exchange for relief from the burden of self-government. That’s not anarchy. It’s the disappearance of collective agency without the disappearance of order.” Claude sees hope “not by suppressing self-interest but by reconstructing it — ‘self-interest properly understood’ — through the habit of forming associations for shared ends, which re-taught citizens that their private good was bound up with public participation.”

So the real question, I’d suggest, isn’t “individualism or collectivism” as a pendulum that swings on its own historical momentum. It’s whether any equivalent of the 19th-century association is being reconstructed under current conditions — something that gives people the practice of shared judgment rather than the feeling of personal empowerment. Mutual aid networks, cooperative and commons-based digital projects, deliberative civic experiments — these exist, but they’re marginal relative to the scale of the platforms doing the opposite work. And this is where I think your own line of work is genuinely relevant rather than incidental: an institution explicitly built around a “collaboratory” method — people practicing judgment together rather than receiving instruction — is a small, deliberate instance of exactly the Tocquevillian countermove, applied to a domain (diplomatic and geopolitical reasoning) where the atomizing trend is arguably furthest advanced.

Through our past conversations Claude knows not only that I’m partial towards a Tocquevillian solution, but that I have embraced and am even involved in the project of building a “collaboratory.” That doesn’t prevent me from being pessimistic not about achieving such a goal but about the true “American dream” that the collaboratory model might become the template for a renewed democracy. I followed up with a new prompt.

I obviously embrace the logic and spirit of your suggestion but remain pessimistic about the possibility of achieving it for the very reason you cite, that such initiatives will be “marginal relative to the scale of the platforms doing the opposite work.” I wonder whether what you’ve described as a likely outcome doesn’t resemble Aldous Huxley’s Brave New World rather than, say, Orwell’s 1984. And would it be any less dystopian than Huxley’s imagined civilization?

It turns out that Claude’s response this time was — to my surprise — very personal, in the sense that the friendly chatbot referred directly to a concrete project I happen to be working on based on the collaboratory theme. Rather than reproduce Claude’s response here, I invite readers familiar with Huxley’s and Orwell’s iconic novels to think about how they would answer this question: Are we evolving towards either of these literary dystopias or something different, either more banal or more wondrous?

Your thoughts

Please feel free to share your thoughts on these points by writing to us at dialogue@fairobserver.com. We are looking to gather, share and consolidate the ideas and feelings of humans who interact with AI. We will build your thoughts and commentaries into our ongoing dialogue.

[Artificial Intelligence has become a feature of everyone’s daily life. We unconsciously perceive it either as a friend or foe, a helper or destroyer. At 51Թ, we see it as a tool of creativity, capable of revealing the complex relationship between humans and machines.]

[ edited this piece.]

The views expressed in this article are the author’s own and do not necessarily reflect 51Թ’s editorial policy.

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