Illicit Gains → Desktoplessness → Sandra Bollocks

Hey Neighbor. True story. Two colleagues take a break from Cannes Lions presentation to walk la Croisette. “We live in New York, but we only hang out in France,” says the first, an attractive woman in her late 30s. The second looks down at his horsebits. “It’s okay this way,” he says. “It’s like Before Sunset.”

The woman smiles wanly. “Let me know if you see Ethan Hawke.”

➺ Thanks to “Adtech Bob” for the anecdote above. If you’ve had a similar close encounter with the Upper Middle, please share.

➺ I’ve been experimenting with the newsletter reader Meco and I dig it. Also, I’m a big fan of today’s sponsor Quince, which actually elevates the basics instead of just talking about it.

➺ Little kids should be legally required to have yellow raincoats. It’s the best.

Upper Middle’s “Small Luxuries” Survey is our attempt to find out what “discretionary” purchases (read: indulgences) are delivering a huge ROI for members of the Oat Milk Elite. Results and dope recs will be shared with survey participants and members.

STATUS ❧ Intrusive Thinkers

What makes the paper Jackson, now an associate professor of sociology at Stanford, published in eight years ago in “The British Journal of Sociology” so compelling? It seems to have been eerily right. Upper Middle spoke with Jackson about her work. The interview has been edited for length and clarity.

In your paper, you take on Liberal Theory, which kind of like fluoride in that it’s in the drinking water. Can you explain the basic premise we’ve all imbibed and why you find it suspect?
The basic idea of liberal theory is that, as time goes on, peoples’ ascribed characteristics – race, gender, class background – become less important in determining success. To some extent, it’s the American Dream, but it’s built on the dual ideas that we’re moving toward meritocracy and that meritocracy should reduce resentments. But how do we define merit? If merit is what the market values that opens a can of worms because employers value social skills shaped by class background. If your professional parents trained you in subtle ways – they likely did – you show up marketable^[1]. What constitutes merit is debatable so meritocracy is as well.

You point out that the core economic experience of the last few decades has been relative loss – kids doing worse than parents, men watching the gender pay gap decrease, blue-collar workers having jobs shipped to China – and that this has resulted in different groups fighting over less. You say those groups are defined by how they think about merit. Why is it coming down to that? 
If I see someone doing well and I think they’ve worked hard and are deserving, I’ll say those gains are licit. But if I think they didn’t deserve it, then I might call it illicit. DEI is a good example. Someone might say: “We’re removing barriers that should never have existed.” But someone else might say: “It’s an overreaction that privileges specific groups.” Whether you call something illicit depends on beliefs about fairness, effort, and history. Conscious or not we go through a process of judgment.

It seems like we see this when Republicans hate on elite universities and Democrats rag on financial services, but this kind of thinking seems common at both extremes. Why is that?
Trump and Sanders both say we’re in zero-sum contests. They claim: “If someone’s getting something, someone else is losing something.” That’s not necessarily wrong –you either put tariffs on or you don’t – but it reorganizes how people see groups, resources, and justice. It reorganizes groups around what gains they think are licit or illicit.

Do you think that the Upper Middle, well-educated urban knowledge workers, constitute a group and, if so, what is the group’s identity and notion of what is and isn’t illicit built around?
You’re talking about people with capital – probably in the form of shares – who work. A longstanding critique of Marxism is that labor has capital. But here’s the thing: Humans are really bad at weighting future gains versus present losses. Even if you have a retirement account that’s growing, the loss of wage growth or job security hits harder. These people experience the world as labor.

In terms of what they find licit, there is an enculturation process happening in universities. What’s unique about the American context is that professionals like lawyers and doctors share that process – to a degree – with managers. In other countries, these are two groups, but mass credentialism has made these folks feel they’re part of the same project whether that’s true or not.

That makes sense, but it also seems true that gains by people involved in financialization would seem illicit compared to the gains of, say, doctors. But we don’t see doctors castigating their college buddies in private equity. Why not?
We’ve divided big tasks up into smaller and smaller tasks so people become specialized. When these people do their jobs diligently and they are hardworking and they perform their roles, we treat that as licit: They are ticking off the tasks that they're supposed to do. I think we're more and more willing to understand our roles in that sense rather than asking if the tasks are actually worth doing or even moral.

Final question. You published this paper in 2018. Looking around now—how does it feel to have been right?
It’s not a happy paper. And I don’t know that we feel vindicated or that we know we’re right just yet. But I think we’re right.

➺ We evolved to know (and care) who will be good at hunting – and it’s a totally useless skill. ➺ “Unless doomers act in ways consistent with their doomer views, it’s fair to assume that they don’t really believe what they’re saying.” ➺ Is integrity back? ➺ “There is a sort of chronic energy deficit that many of us experience. We alternate between apathy, anxiety, and daydreaming.”

TASTE ❧ Sandra Bollocks

Materialists, Celine Song’s follow-up to the critically tongue-bathed Past Lives, is an unromantic uncomedy about “value” in relationships and assortative marriage (people ringing up within their class), which is on an exponential upswing thanks to social signaling on the apps. The twist in the screwball setup – Dakota Johnson plays a cynical matchmaker^[2] – is that Song, a former matchmaker herself, seems to think assortative marriage is good, actually. It’s a notion worth entertaining, but a super odd subject for entertainment.

There are essentially two ways of considering value and class in relationships. The first is that people pair off to maximize joint well-being. That doesn’t sound romantic, but it is. The second is that people pair off with partners who mix money and intimacy in the same ways they do. That sounds romantic, but it isn’t. How we mix capital and care is inevitably rooted in socio-economic experience.

In essence, Materialists is a rejection of Two Weeks Notice or You’ve Got Mail, in which couples cross class lines because they’re good for each other. It’s more neatly aligned with The Philadelphia Story^[3], a Wharton-y movie about the preservation of country club society that came out 85 years ago and has a similar setup, payoff, and voyeuristic appeal – “The prettiest sight in this fine, pretty world is the privileged class enjoying its privileges,” quips Jimmy Stewart. He’s right, but also a buzzkill. It’s okay to need a sip of champagne.

➺ Smart takes are a luxury good. ➺ The coloring book of the year just dropped. Give it a Pulitzer. ➺ Biceps are the new tennis bracelet. ➺ The coolest book to have just kinda laying around (for a certain kind of person). ➺ Why argue?

MONEY ❧ Desktopless

The worst thing about 2025 – aside from all the other things – is that July 5, the least productive day of the year (40% of workers take it off), falls on a Saturday. But there’s productivity and productivity. For people with Director or VP titles, hired to think and given no time to do it, a slow summer day is often more productive.

Not having to worry about a boss off masticating tripe of the literal or Walter Isaacson variety on the beach in Cannes or engaging with Craig from Ops on the Q3 roadmap means means being able to work without having to perform work. It’s a regularly scheduled reminder that while performing work sucks, what the thinkbois call “deep work” doesn’t. (And a good reason not to take time off in July or early August.)

Many members of the professional managerial class have joined or been dragooned into cults of collaboration. Yes, collaboration can be great, but its principal virtue is that it produces deliverables that seem like productivity. When the opportunity to collaborate is eliminated, an opportunity for something else emerges.^[4] Not all changes need to be tracked.

➺ It’s the mortgages, stupid. ➺ Outlook data suggest 40% of workers are online by 6AM. ➺ The Labubu bet is Gamestop for morons (and it’s working). ➺ Who is actually buying up homes? Mom and pop investors. ➺ And Europe will get 10% more expensive. Time to go to Croatia?

[2] The idea of being a matchmaker for rich people makes sense on paper, but rich people are the only discreet segment of the population small enough that no introductions are required.

[3] Celine Song released a list of movies that inspired Materialists and The Philadelphia Story isn’t at the top of it, which is pretty wild. But there is a huge stylistic difference around voices. Cary Grant and Jimmy Stewart do cartoonish class dialects in that film. In Materialists Dakota Johnson talks like Dakota Johnson, who talks like she went to a fancy finishing school and majored in murmuring. It’s incredibly odd and completely undermines the idea that the movie is keenly observant about anything.

[4] The only thing I really miss about working in a corporate setting is that feeling of coming in early and having the place to yourself. Drinking a coffee and sipping your little thoughts. I loved that, which, I suppose, is why I don’t work in a corporate setting any more.