For the Comfortably Uncomfortable



Personal Time
Bandits
Corporate America was built by war heroes then rebuilt by greedy hippies. No wonder Silicon Valley went from white collar to brownshirt so fast.

For most of our history, professions were heritable in the form of tools, land, and
know-how. All the changed when Horace the tinsmith and Zebulon the wheelwright skittered toward the factories the skittered home to teach little Jeb and Marla “work ethic” rather than, you know, skills....


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Vanity Metrics
Good taste use to be a good business. Now, it’s an obstacle for big businesses looking to scale ad revenue. It’s why you’ll be reading more and more about cruises and less and less about Umbria.

Targeting data makes culture into a diagnostic rather than project, driving down – in a very real financial sense – the value of the sort of curation most lifestyle publishers were created to do.



Europe, California
As the American frontier closed, violence became entwined with ambition. Why would it be any different in the NIMBY-filled suburbs?

Sometime around 1880, Mark Twain leaned back in a Morris chair or a stupor or both and quipped: “Buy land. They’re not making any more of it.” That quote is now regurgitated birdlike by every visiting drunkle with a BA in economics. But Twain wasn’t talking about investments.







Rabbi-Curious
Yids and Micks locked out of elite industries built the modern media then used the modern media to rebuild the elite. Guess who ain’t so happy about it? The Mayflower Mafia.

Just beneath reactionary caterwauling about liberal media bias lies a Protestant cultural anxiety about the intellectual ascendance of non-Protestants in America. The real objection is to a religious – yes, religious – preference for shared truth over individual truth.





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

Thursday - Sept. 11, 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

Higher E.D.

Over the last few years, Brandon Christensen has invited dozens of students into his CU Boulder lab and made them feel extremely awkward. A PhD candidate studying luxury consumption, Christensen asked students to name their preferred brands—cars, sunglasses, laptops—then asked again after telling them they would be flaunting those goods in front of someone less affluent. The speed with which they retreated from ostentation served as his measure of “exclusivity discomfort.” He found E.D. correlated with social proximity; intimacy increased discomfort.

Like a Roth’s liver-humping Alexander Portnoy, Christensen also found that E.D. was most pronounced around vacay. Participants admitted they’d be far less likely to share, brag about, or mention a high-end European trip or safari with someone more used to flying to Spirit to Boca. They’d still go to Santorini (natch), but they’d whitewash it as a “retreat” to anyone without 50,000 American Express Rewards points. That finding suggests an alt explanation for why the PreCheck Elite splurge on experiences, not goods: We want to hide the evidence.
Taste

Getting Chintzy With It

The big swinging zizis of 19th-century French lit (Balzac, Flaubert, Maupassant) loved skewering the hobereaux, those petty nobles clinging to their titles and terriers in crumbling country piles. Fading aristocracy was a mood then, and it’s a mood now. Strip out the Sun King chandeliers and the hobereau aesthetic is basically heritage maximalism – today’s shelter-mag obsession – surfacing just as Millennials give the half-dead antiques market chest compressions. Threadbare Persian runners, Staffordshire dogs, supper clubs, and book circles are back along with other signs of managed social decline. 

And yes, it’s gorgeous – even the trailer for Emerald Fennell’s brain rot Wuthering Heights. But that’s the ruse.Maximalism is for conversationalists without conversation pieces. Put enough photos in enough gilded frames and no one will notice the chips or the state of the wallpaper. The look says permanence when the bank balance says the opposite. Still, if it finally buries beige minimalism, then, whatever the cost, ça fait plaisir.

Money


Medfuuud

Colleges are trading tuition for paywalls. This fall, two of Boston’s most exclusive institutions and Tufts2 announced free tuition for “middle-income” students. At Harvard and MIT, that means parents making under $200K. At Tufts, the cutoff is $150K and the language is blunt. In announcing the “pact,” Dean of Admissions J.T. Duck called the university’s $71,982 tuition a “sticker price,” explicitly leaving room for discounts.

That framing isn’t coming from nowhere. It’s coming from 620 Eighth Avenue, aka NYT HQ. Over the past decade, the Grey Lady survived while other prestige brands shrank because it built a smarter paywall. The paper sets a $25/month sticker price but almost nobody pays that. Tufts now faces a similar problem the Times cracked in the 2010s: How to stay elite-ish in a crowded market. One answer was high sticker prices and targeted discounts. The other was Wordle3. The new Tufts Tennis Center has much more spectator seating. Go Jumbos.




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.

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 
UPGRADE TO JOIN
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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