Bottled Elites

In 1921, the Pulitzer Prize jury for fiction selected Sinclair Lewis’s Main Street, but the Pulitzer Board vetoed the choice. The board, led by Columbia University president Nicholas Murray Butler, claimed that Lewis’s satire of small-town intransigence was acidic, cynical, and therefore an inappropriate choice for a prize that – at that time – was supposed to be awarded to books celebrating “the wholesome atmosphere of American life and the highest standard of American manners and manhood.”

Main Street portrayed provincial Americans as vicious and parochial, so the Board gave the prize to Edith Wharton’s The Age of Innocence, which portrayed New York’s urban elite as vicious and parochial. The irony wasn’t lost on Lewis and Wharton, who thought of themselves as participants in the same project. Both sought to honestly capture the material circumstances, social mores, and hypocrisies of Americans – different kinds of Americans, sure, but Americans all the same.

“The greatest mystery about a human being,” Lewis wrote in Main Street, “is not his reaction to sex or praise, but the manner in which he contrives to put in twenty-four hours a day.”

Increasingly, the current equivalents of Wharton’s decorous, two-faced urban elites are changing how they “put in twenty-four” by heading for Main Street. They are starting or buying small companies. They are leaving large ones¹. Though coverage of the “Great Resignation” stopped in 2022 and the narrative has turned toward “job hugging,” the exodus never really ended. Through 2024 and into 2025, roughly 3 million Americans a month quit their jobs – well above pre-pandemic norms. Gallup surveys show nearly 60% of workers describe themselves as psychologically detached. Even within glassy downtown skyscrapers, what looks like quietude is often the prelude to a resignation, and many firings are justified by total disengagement.

It’s tempting to characterize highly credentialed corporate defectors as “downwardly mobile elites,” but that misunderstands the historical context, the elite demimonde, and Main Street itself. These people aren’t sliding down; they’re moving orthogonally across a plot of personal values, away from institutionalism and consumerism (the things you can get a Pulitzer Prize for mocking) toward individualism and thrift (the things you can’t). The bottled elite—all those Slack users—are spraying out into the world with force. It’s a messy, uncontrollable process, but it’s a mistake to assume that temporary chaos will lead to lasting disorder. It won’t.

The Age of Innocence is set in the 1870s, which is more or less when elites got bottled in the first place. In the late nineteenth century, America rapidly transformed from a patchwork of self-reliant communities into a nation of bureaucracies, professional associations, and corporations. The scholar Robert H. Wiebe described this as the “organizational revolution.” The thing that got overthrown was American self-reliance. This became an institutional country with a stronger national identity rooted in national organizations and organizational hierarchies².

“The heart of the modern American system [became] organization,” Wiebe wrote in The Search for Order, 1877–1920, “an order of interlocking structures that bound men together even as it restrained them.”

That restraint, it’s worth pointing out, came with significant purchasing power. To wildly shorten a long story: post-organizational-revolution America became a rich, corporatist country—with much of that growth coming after WWII at a moment of heightened organization and national pride. Between 1947 and 1973, real median family income in the United States more than doubled, rising from roughly $29,000 to $59,000 in today’s dollars, while productivity grew at a similar pace. The average manufacturing worker in 1970 earned enough to buy a home, raise a family, and send children to college.

Things were good (for white people), but a paradigm had flipped. For most of the nineteenth century, Americans expressed themselves through production and practiced consumer restraint. For most of the twentieth, they expressed themselves through consumption and practiced professional restraint.

But as the century closed, restraint became pressure. In The Meritocracy Trap, Yalie dissident Daniel Markovits describes how the very institutions built to democratize opportunity became engines of overwork and anxiety. Elite professionals—lawyers, bankers, consultants, engineers – found themselves laboring under a system that demanded endless striving but no longer rewarded it. From 2000 to 2020, inflation-adjusted wages for doctors, lawyers, and consultants barely moved even as the workweek lengthened by nearly twenty percent. Corporate profits soared, but the share of national income going to labor fell from 66 percent in 2000 to about 58 percent in 2020. This was keenly felt by middle managers. Pressure built.

And while the pressure mounted, some folks shook the bottle. Since the 1980s, right-wing think tanks like the American Enterprise Institute have argued that capital should be taxed more lightly than labor – a project so successful it now forms the backbone of U.S. fiscal policy. The result is that the people who make organizations run – corporate lawyers, senior engineers, mid-level executives – face high marginal tax rates with few deductions while business owners and investors glide by at closer to 20 percent. The tax code is violently regressive near the top. It doesn’t just reward ownership; it punishes the other kind of success.

No wonder the cork is popping.

In 2025, roughly 5–6 percent of Harvard MBAs chose to pursue Entrepreneurship Through Acquisition – buying HVAC companies, auto repair shops, dental labs (solid, cash-flowing enterprises) rather than joining consulting firms or hedge funds. That number isn’t massive, but it’s climbing quickly. Codie Sanchez, a former private equity investor turned small-business evangelist, calls it “a golden era for business buying,” citing the demographic wave of 4.1 million Baby Boomers retiring every year and an abundance of profitable, ownerless firms.

This opportunity is the product of the organizational revolution. Main Street businesses are cheap, stable, and historically ignored by elites too busy chasing brass rings in the form of titles at big brands (many of which can’t turn a profit) to double-click on their margins. Main Street entrepreneurship solves two problems: how to make money, and how to put in twenty-four hours a day. Entrepreneurship allows elites to regain control of their lives. But there’s a wrinkle: it also makes their lives hard to talk about with other elites.

The social costs of moving from an institutional, consumerist lifestyle to an independent, frugal one are real. For decades, the question “What do you do?” has preceded most cocktail party conversations between strangers. The reason is simple: in the elite demimonde, job titles served as shorthand for identity. Now, as people step away from those titles, they are discovering how difficult it is to describe themselves in the language of actions rather than affiliation.

I’ll slip into the first person here, because I feel this keenly. Before starting Upper Middle, I held a privileged perch at a large media company bound by an NDA. I loathed the job—it felt like rearranging deck chairs on a torpedoed submarine—but the title made me sound cool at parties. After being fired for repeatedly, publicly, and relentlessly antagonizing management, I started building something I’m proud of and that, long-term, will likely pay better. Still, I’m uncomfortable talking about it because there’s no credential attached. I didn’t earn my job as editor of Upper Middle; I gave it to myself.

As someone who’s always kept fancy credentials at arm’s length, I feel humiliated when I reach for one and come up empty. The feeling persists even though there’s nothing else I’d rather be doing.

Anthropologists Arnold van Gennep and Victor Turner would call this phase “liminal” – the “betwixt and between” state when an old identity is gone but a new one hasn’t formed. The loss of a script is unsettling because social life runs on scripts. Management scholar Herminia Ibarra notes that professionals in transition test “provisional selves,” experimenting with new stories until one fits. I find this too, though experimenting in public is embarrassing.

Still, liminality has perks—big ones. Cate Hall, author of the forthcoming You Can Just Do Stuff and CEO of Astera³, calls them the “Moat of Low Status.” The discomfort of learning by doing – and failing – scares many institutional elites into staying put, shrinking competition in the spaces where there’s no other way to learn. People who are used to being good at things don’t like to be bad at them, even temporarily. That’s the delicacy of the elite – what both Wharton and Sanchez write about. It’s staying in the bottle to stay on the top shelf.

As the organizational revolution sputters out – dysfunctional government, loss of public trust, anti-corporate sentiment, anti-scientific movements, crypto, etc. – that kind of inertia makes less and less sense. The new old ways don’t work so well anymore.

One of the reasons the Pulitzer Board didn’t want to celebrate Main Street is that the elite have continued to enforce a century old cultural omertà on mocking “Real Americans.” Satirizing small-town life is far less acceptable in this country than poking upper-middle pretension. There’s nothing inherently wrong with that – privileged people ought to be able to take a fucking joke – but it does create a cultural blind spot. Many Americans, and particularly the sorts of people who identify as “Real Americans,” believe that elites are incapable of do what they do. This belief is persistent because it’s largely untested. For a very long time, elites didn’t want to compete on Main Street. Now some do. Plenty of people within that cohort who aren’t just well-educated and credentialed, but insanely hard-working, which means that the people who thought it was a good idea to shake the bottle are about to get a cork in the eye.

Whatever else you can say about the disillusioned professional class, we are trained for competition. It may not be likable to say it, but the smart money is on the MBAs⁴. 

Still, rough transition.

In 1926, five years after the Main Street debacle, the Pulitzer Board decided to award Sinclair Lewis’s Arrowsmith the Pulitzer Prize for Fiction. Lewis turned them down. In a public letter to the Pulitzer committee, he explained that he would not “accept an award that limits itself to ‘wholesome’ American life, when the life I know is sometimes unwholesome, often sordid, and always varied.” The letter was a big middle finger to the cultural establishment from a Midwestern guy who went to Yale and married a Vogue editor. Lewis was elite and independent. He saw the power in that. In Main Street, he even described it – explaining in third-person omniscient what made his heroine special.

“Whatever she might become she would never be static.”

And that’s the crux of it. You can’t stuff that kind of person – that unusual kind of American – back in the bottle. They fizz out into the world with foam and force.