For the Uncomfortably Comfortable



The Bottled
    Elite
“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.”

Across America, professional elites are rethinking how they put in twenty-four. The shift coming could change real Main Streets forever (and probably for the better).



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Task Masters
There’s been a prestige inversion for white collar workers. Profits used to follow the product and prestige followed the profits. Not anymore.

Financialization has altered the job landscape and created a dynamic where employment is a certification (not unlike a college degree) awarded to people who get in, not people who build. That’s great news for low-conviction floaters....



Make it Up in Volume
The fight over free speech matters, but the fight over paid speech will ultimately determine the direction of American culture (whether the New York cocktail party crowd likes it or not).

Why? Because there’s a natural antipathy between people who think attention should be earned and people who don’t mind just buying it. And, yes, it’s exact the sort of elite conflict that has historically started in boardrooms and ended in the street.


How to Buy Friends
You have close friends from college for a reason and it has way less to do with shared interests than you might think.

Proximity – propinquity, really – leads to friendship. Unfortunately, it happens to be the very thing the busy, high-earning Americans trade for convenience. What if we didn’t?








Prep Effects  ➺ Semiconfabulators ➺ Caddyshackles ➺ Effable Studs ➺ Polo Bearishness ➺ Socialized Headline ➺ Passive Regression ➺ Oolong Tea Party ➺ Horace Mayonnaise ➺ Weaponized Ambiance ➺ Loyalty Programmed ➺ Resting Rich Face ➺ Desktoplessness ➺ Fractal Snobbery ➺ Excessive Thrift ➺ Gen Executor ➺ Engineered Elites ➺ Leveraged Despair ➺ Professional Chicken ➺ Empirical Violence ➺ Rich Friend Gaps ➺ High-Stakes Bullshit

The Cheatsheet

Friday - Oct. 17, 2025
A thrice-weekly pre-dinner briefing for busy professionals who want to know just enough to seem like they know everything, Upper Middle’s “Cheatsheet” is the antidote to asp-y Axios apocrypha – a social briefing for people who care about status, taste, money, and how they co-mingle.

Status

Cluster Proms
Good fences make good neighbors. Good neighbors make good fencing teams.

According to a new nationwide spatial econometric study (I know, you just can't get enough of them), it's no longer enough to move to the right town with the best school; you have to move to the right cluster with the strong intra-school rivalries. Students in districts located within high-performing clusters (think: Scarsdale-Bronxville-Pelham in New York, Palo Alto-Cupertino-Los Altos in California) now score 0.35-.4 standard deviations higher in math than students in wealthy enclaves. That may not sound like much, but it's roughly equal to a month of learning per year. 

Study author Samantha Traves, a PhD candidate at McGill, discovered this phenomenon, which she's dubbed “concentrated advantage,” by flipping academic inequality scholarship on its head. Rather than focusing on how poor schools got that way – generally bad state policy and funding issues – she focused on how rich schools got rich. The driver turned out not to be policy or funding or taxes. Clusters emerged, she found, because white-collar professionals seek each other out, moving to academically and culturally homogenous areas.

Here's why it happens: Once a few adjacent districts get a good rep, high-income families start home shopping, driving up property values, boosting local budgets, and creating both a competitive market for teaching talent and inter-district competition as educators scramble to outscore and out-AP class each other. An enclave becomes an area becomes a cluster becomes a fortress (protected by children with swords).
Taste

Needing the Eggs
Since her death on October 11, a lot of words have been used to describe Diane Keaton. One that hasn’t: fellatrix. It’s the word Woody Allen – a perv and a prick – used to describe his ex, muse, and ex-muse during her AFI lifetime-achievement tribute. A shitty thing to say? Sure. A gross way for Allen to assert co-authorship of Keaton’s public image? Absolutely. Inaccurate? Seemingly not. Keaton was the rare sex symbol whose appeal was rooted less in desirability than in her own desire. She was a nice, educated woman who liked sex. 

Keaton wasn’t coy about it. “I learned I couldn't shed light on love other than to feel its comings and goings and be grateful,” she wrote in her autobiography Then Again. Her characters seemed to share that openness – from Annie Hall (“You wanna come upstairs? I’m gonna sing.”) to Looking for Mr. Goodbar (“I just want to feel something.”) to Something’s Gotta Give (“You don’t understand – I like sex!”) – she played women adept at navigating pricks. Pauline Kael once said Keaton “suggests a woman who might actually like men.” That was the core of her very specific shiksappeal; her sexuality was her own. 

Keaton will be remembered as a great actress because she was a great actress and as an iconoclast because she was an iconoclast. But it's also worth mentioning what she wasn't: ashamed. Beneath the neurotic stammering and the suit jackets was a singular confidence and comfort that everyone wanted one way or another. That’s what Annie Hall was about, and it’s why Woody kept popping up wherever Diane went.
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Money


Luxcotting
The Fed’s October Beige Book, quilted together by the 12 districts, paints a pointillistic picture of a bifurcated economy. Nationally, spending has “inched down,” yet retail sales and tourism in Boston, New York, and San Francisco have been buoyed by luxury segments. In Atlanta, the high-end home market is “resilient” though demand for starter homes is sliding. Outside Chicago, spending on landscaping is “healthy" though fast casual restaurants are feeling a pinch. Beige story short: semi-rich high earners (wassup homie) are spending enough to obscure a middle-class recession. The “Trump Economy” rests mostly on the shoulders of people who didn’t vote for him.

There’s precedent for coastal American elites having this kind of leverage over a government hostile to their best interests (Trump II’s policies make it clear Don is fine King George-ing the ’burbs). In 1768, Boston’s merchant class signed the Non-Importation Agreements, pledging to halt purchases of British goods. Their boycott was deliberate, measured4 reaction to the Townshend Duties of 1767, which taxed imported glass, paper, paint, lead, and tea. Those new duties didn’t crush commerce, but they set a dangerous precedent: taxation without representation. Within two years, London exporters, losing revenue, pressed Parliament to repeal most of the duties.

Today’s professional class sits in a similar position: antagonized by a government hostile to the institutions and cities that define them. A quiet economic abstention would be powerful, but… will we do it? It’s hard not to be skeptical. We don’t seem ready to throw our Chase Sapphire cards into the Hudson just yet. But maybe it gets there.




STATUS REPORTS

Upper Middle’s “Status Reports” use survey data to decode how social, cultural, and financial capital shape both our choices and our sense of self. Each report draws on correlations to expose impulse-driving biases and the subtle ways we’ve been socialized—for better and for worse. In understanding people like us, we understand ourselves.

GUILTY PLEASURESThe Upper Middle “Very Guilty Pleasures” examines how elites think about the their least elite habits and behaviors – and why we can’t help but hate ourselves. 764—39/23 
Doc—45456



EASE MAXXING

The Upper Middle “Self-Presentation Survey” examined how we present ourselves in social settings – particularly among perceived peers. Specifically, it dove deep on soft signaling.
764—39/23
Doc—45456


RARIFIED WILDS

The Upper Middle “Outdoorsy Survey” examined how we engage with, conceptualize, and fetishize nature. The survey data suggests that Nalgene-carrying weekend trippers clustered in metroplexes valorize “pure” nature, but can’t necessarily afford it.
764—39/23
Doc—45456



ANTSY NEIGHBORS

Our “Where Next Survey” explored how we think about moving: not just where we might go, but how we consider what those choices say about our class position, taste, and willingness to compromise. The results indicate that we’re house-proud and restless,
764—39/23
Doc—45456



Zero-Martini Lunches 
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A live conversation series with authors and scholars on the forces shaping this privileged American life, “Zero-Martini Lunches” are Chatham House Rules forums where big ideas get batted around while everyone eats sad desk salads. The one Zoom meeting you’ll actually look forward to attending.

 
Ruth Braunstein
AndreaCampbell
Eunji Kim
Megan Greenwell
Michael Grynbaum
Leigh Clare La Berge
Augustine Sedgwick
Michelle Jackson
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The Editor

An award-winning & losing journalist, Andrew Burmon has served as the Editor of Inverse, Fatherly, and SPY. He is the co-author of Fatherhood (Harper Horizon) and the product of elite schools, New England ennui, psychopharmacology, Catholic/ Jewish guilt, too many books, smart women, and his own bad decisions. As an infant, he pulled the silver spoon from his mouth, stuck it in his eye, and cried.





                   




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