Con Artistry → Tasteful Brandhumping → Leveraged Despair

Hey Neighbor. True story. Two friends on line for goat cheese in the San Francisco Ferry Building. “I don’t think microdosing does anything,” says the first. “I think people who don’t want to think of themselves as square just want to remind everyone they do drugs.” The second nods and considers.

“I had a bad acid trip a few months back,” he says. “I thought I was a cube.”

➺ Thank you to readers/members who took our admittedly odd “Status Symbols” survey. The data was wild and fun to comb through. Learned a lot about handbags – also, cars.

➺ A respectful nod to “Suck Falesforce” (no notes) in CA for the anecdote above. If you’ve heard something undeniably Upper Middle recently please share. Be a snitch!

➺ I’ve been using Sanebox recently to manage my endless stupid emails so I asked them to give all of us a discount and they did. Recommend.

➺ About 135K readers later, Upper Middle has an artisanally coded homepage.

Upper Middle’s Q2, 2025 “A.I Invasion” Survey is our attempt to document how the oat milk elite is preparing (or not) to face the downstream effects of A.I. adoption in the workplace.is our attempt to find out how members of the oat milk elite are flaunting their social rank and how those efforts are going down with their less cringe-y peers. Data will be shared with survey participants and, as always, with members.

MONEY ❧ Deep State of Depression

“That’s what the money’s for!” – Don Draper’s backhanded dismal of a mentee’s need for validation – became an instant meme back in 2010. It was digested by smug Boomers and MBA tryhards as hometruth. But it was a lie. Money is compensatory. Validation is edifying. The fact they tend to be negatively correlated – people who pursue a purpose generally make less – underscores the self-serving stupidity of conflating the two.

The Draper meme is old and the counterargument, better known as “The Protestant Ethic,”^[1] is even older, but old doesn’t mean irrelevant. Yesterday, Elon Musk took his leave from Washington. The billionaire’s exit pursued by bearish Tesla trading was covered as a retreat, but Musk's swamp offensive was an insurgency not an occupation. By shitcanning 125,000 professionals called to public service (and certainly a few folks loafing towards sinecures), Musk blew up a pipeline. Fewer smart people willing to trade money for earned validation will seek government jobs. Talent will spill into the private sector.

Economists estimate that mass layoffs result in one additional suicide for every 4,200 men or 7,100 women purged. Those numbers tend to be higher among those with callings (studies of Britain’s NHS suggest female physicians have a 76% higher suicide than gen pop). Stories about ex-government employees are starting to surface. There will be more. This should come as a shock, not a surprise because it was a feature, not a bug of Musk’s approach, which many employers will now ape under the auspices of AI adoption. Despair is leverage.

Despite demonstrating no real savings, Musk argued the cuts were about money. Nope. They were about withholding validation – withholding meaning. Only a villain or a mad man would confuse the two..

➺ The “First Sale Rule” is a pretty obvious (and pretty funny) tariff workaround and maybe a good reason to go shop in Hong Kong. ➺ The editor of People Matters, a B2B pub for HR professionals, has entered the running for Credulous Idiot of the Year thanks to this hed: “McKinsey Rejects Layoff Claims – Attributes Headcount Drop to Performance Reviews, Not Job Cuts.” ➺ Trumps wealth, and thus his self-identity, is now wrapped up in Bitcoin. Behave accordingly.

TASTE ❧ Talking Pieces

Talking Pieces is a recurring feature highlighting Upper Middle members with great taste and nice stuff. Think that describes you? Let us know.

Name: Gab Saper
Job: Personal stylist, founder of Wardrobe Editor
Location: Greenwich Village, Manhattan
Rating of City: 9 (out of 10)

Gab Saper and her husband bought in the Village during Covid. It was strange timing, but also a rare opportunity to grab a two-bedroom coop for below listing. The 17th-floor apartment overlooks an intersection near Union Square and you can see the Hudson River if you’re standing in precisely the right spot. The Sapers took their time decorating. “We don't like to have a lot of things,” Gab says, “but the things we have speak loudly.”

➺ Jesse Welles is a weird angry genius at a moment when we need weird angry geniuses. ➺ Starbucks isn’t a coffee place. It’s a bank. (Which explains the coffee.) ➺ It’s a really good time to go to São Paulo FWIW. ➺ “The emphasis on temperature over quality suggests a semi-ironic, intentional self-bimbo-ficiation. After so much pretense, so many years of trying to prove you know what you’re talking about, it can feel good to be a ditz.” ➺ Critics aren’t loving The Phoenician Scheme, which is a really good sign TBH.

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