A few issues back, we introduced Spencer: the modern optimized professional.

He works in consulting, finance, or SaaS (now rebranded as “AI”). Spencer tracks his sleep and his life. He walks on a treadmill desk while listening to podcasts at 2.5x speed. Spencer hits Vyvance, Zyn, and Yerba Mate to respond to Slack at 11:32pm.  

But Spencer did not emerge from the mist like an athleisure-clad swamp thing. Spencer had a father: the original performance-enhancing professional, Tripp McCall.

In 1986, Tripp was 31. Recently promoted, lightly overextended, physically fit, professionally exhausted, and proud of the fact that he learned to order (and eat) sushi properly — on the expense account.

Tripp drove to the firm in his new BMW. Clad in a tailored suit like Richard Gere in American Gigolo. He didn’t have nootropics and adderall. He had Peruvian marching powder. 

After a few years on Wall Street, where he learned to keep what you kill and how to play squash, he’s back in Richmond — teaching his Collegiate chums how to play liar’s poker.

Tripp didn’t bother tracking his sleep. He simply didn’t get much. His tech was a beeper, and his chest pain was “probably nothing.”  

Spencer’s father was a yuppie. Once mocked as a cultural caricature, but now relevant again as we see Tripp’s 1980s status anxiety as a warning flare: 

Tripp thought he was becoming free. Spencer inherited the machine. Different costume. Same anxiety. And we see the threads of Tripp’s suspenders coming back into our culture. 

American Psycho is more popular than ever. New releases, from the expertly crafted book, Yuppies, to the must-watch HBO documentary Bring Me the Beauties, tell us this era’s story with a new perspective. Meanwhile, Gen Z covets the world of Ralph Lauren. 

But maybe the way to win the game is to stop playing the game altogether. And the next form of luxury is not more refinement, more ambition, or more carefully curated abundance. It’s subtraction.

Tripp thought he was becoming free. Spencer inherited the machine. But the ultimate status move is learning how to step off of it. 

To understand Spencer, you have to study Tripp’s bookshelf, dinner reservations, and dry-cleaning bill. 

Here’s the original source code from the cultural archives of the 1980s yuppie: 

1. TIME, “Here Come the Yuppies!” — 1984
The definitive mainstream snapshot. It gives you the food, vacation, interiors, fitness, real estate, and self-serious absurdity. The “Yupification of a neighborhood” description links directly to today’s gentrification discourse — while the breakdown of interior design choices and travel destinations reads like a pre-internet Pinterest mood board. 

READ: HERE COME THE YUPPIES (TIME) →

2. The Yuppie Handbook
Less a book recommendation and more a found artifact. Riding the waves of Birmbach’s The Preppy Handbook, this cultural fossil is part satire, part instruction manual, part prophecy. An Except: 

“Like Yuppies everywhere, Michael and Jennifer’s most cherished goals are: 

DISCOVER: THE YUPPIE HANDBOOK ARTIFACT →

3. Bret Easton Ellis, Jay McInerney, and Tom Wolfe’s Bonfire of the Vanities
The definitive literary soundtrack of the era: coke, clubs, empty surfaces, spiritual alienation, beautiful apartments, moral vacancy, and young people who have everything except a center.

You know American Psycho but Bonfire of the Vanities was the original zeitgeist symbol. Tom Wolfe captures the essence of New York City in the 1980s. Beneath the “Masters of the Universe” surface, was a dark core of greed, cultural tension, and spiritual emptiness in good tailoring.  

The literary brat pack playlist: 

Putting it in context today, this new book release shows how the yuppies reshaped New York. Seeing how over 50% of Princeton’s 1986 graduating class applied to a single bank, author Dylan Gottlieb knew a major change was in the air. Four decades later, he connects the dots. 

4. Dylan Gottlieb’s Yuppies
This gives the issue intellectual heft. His book, as described in reviews and his own material, connects yuppies to the rise of finance, law, urban reinvention, and the reshaping of New York’s professional class. 

READ: YUPPIES (GOTTLIEB) →

Tripp entered this world when the deal seemed glamorous.Spencer inherited it as the glamour was replaced by dashboards. But it was a harsher bargain than either of them realized. 

The Yuppies of the 1980s helped redesign the professional workplace into an extraction machine. Bigger firms. Larger debts. More competition. 

This Aeon piece will hit hard for anyone that’s ever grinded out a spreadsheet or pitch deck at 2am in some glass building in Midtown Manhattan, Uptown Charlotte, or SoMA in the Bay. The essay examines the grueling, soul-sucking work culture at law firms, its primary focus, and similar paths like banking and consulting. 

Year by year, conditions deteriorated. White-collar workers became more like cogs in a machine than valued apprentices on the partnership path. By the end of the 1980s, it was impossible to ignore how much lawyers were suffering. 

Studies from the article quantify the depths of that suffering: Attorneys had the highest suicide rate of any profession. One in five were alcoholics. They got depressed at six times the rate of the general population. 

But a wider shift was happening. It wasn’t just lawyers. And it didn’t stop in the 1980s. If anything, it only got worse. 

"Today, the members of the newly diverse professional class work much harder, in far more competitive environments, with slimmer chances for advancement. From Seattle to New York, young professionals whisper that their firms have become ‘sweatshops’: factories where profits are squeezed out of their white-collar labour force.”

The professional class was sold freedom and given a wood-paneled factory. The key takeaway here is not anti-ambition or hard work. It’s the dangers of unexamined ambition. The emptiness that leads to chasing titles, adulation, and a bigger bonus at the cost of your health, family, and identity. 

This is not an exit. 

READ: WHITE COLLAR SWEATSHOPS →

As they say, “evil doesn’t die, it just reinvents itself.” 

Joking (kind of). 

So let’s compare and contrast Tripp and Spencer — a field guide to the yuppie of the 80s vs. today: 

In 1986, Tripp told his analyst “if you want friends, get a dog.” In 2026, his son Spencer considers his Doodle his best friend as he delays kids for another year. 

Tripp screamed “fuck you!” into the phone after executing a trade. Spencer dreams of making “fuck you money” while spinning up slides in Claude and taking a bite of his Cava lunch.

Tripp wore his ambition loudly. Spencer wears it quietly, and more casually. 

They both love music. Tripp got amped with Talking Heads tapes on his Walkman. Spencer matches his vibe with a pre-made Spotify playlist and jams out with his Airpods. 

Here’s some more generalized observations, not a unified theory of our professional class. Take them lightly, have some fun, and see if you can recognize these characters:

Tripp and Spencer aren’t bad guys. They’re just people trying to solve the riddle we’re all working on: how to build a good life when the goalposts keep moving. 

When you step on the white-collar treadmill it’s hard to step off, and after a long enough time you don’t know what you’re chasing and why you started in the first place. 

Justin Welsh has a great piece that reframes modern luxury — in a similar way that we did in past issues — as the ability to think clearly, sleep deeply, move slowly, and live quietly in a world designed to prevent those things. 

Welsh argues that calm is fought for by removing the wrong things, not adding more “right” things. We see this play out in modern culture. Eschewing the hyper-connected digital world and optimization for the things we should’ve been chasing all along. Some examples: 

DISCOVER: WHY MODERN LUXURY IS SUBTRACTION (JUSTIN WELSH) →

The 1980s yuppie treated food as sophistication signaling: sushi, tortellini, chef salad, espresso, white wine, “undiscovered” restaurants. TIME’s archive captures this beautifully. 

But then steakhouse lunches gave way to slop bowls. A good scotch was replaced by a green juice. Sushi and wine went from marks of sophistication to mass market grocery stores. 

Here’s the menu for Tripp and Spencer: 

Tripp, 1986: 

Spencer, 2026:

Our angle: we don’t think your choice of drink or grocery store says anything about you. And the best meal is still the one that doesn’t need to become content. We love a good club sandwich, steakhouse lunch, and think espresso is the best thing you can order at Starbucks. 

For all their striving and absurdity, the yuppies got a few things right: durable clothes, racquet sports, and a few staples that withstood the test of time. 

1. L.L. Bean Duck Boots 

A true icon that has maintained its quality, rugged durability, and Maine manufactured craftsmanship for over 100 years. 

SHOP: THE ORIGINAL BEAN BOOTS →

2. The Classic American Oxford

I’ve embraced the Oxford shirt as a uniform staple for a decade. It’s highly versatile, sporty yet refined, and an All-American classic that never goes out of style.  

The Zephyr Oxford from Gitman Bros. is breathable, quietly refined, and made by hand in Tennessee. 

SHOP: GITMAN BROS ZEPHYR OXFORD →

3. Tennis, Anyone? 

Studies crown tennis as the healthiest sport, adding up to 9.7 years to your life expectancy. It’s also a social game that doesn’t take up your entire day. I’ve loved playing tennis ever since I picked up a racquet. So I’m pleased to see the game’s resurgence and renewed interest.

Lacoste — A symbol of the 1980s yuppie is still a classic, on and off the court. 

SHOP: LACOSTE CLASSIC TENNIS SHIRTS →

Uomo Sport — A new tennis brand that reinvents the timeless aesthetic of tennis’ heritage. Made in the USA with premium Italian fabrics. 

SHOP: UOMO SPORT LUXURY TENNIS APPAREL →

The Inner Game of Tennis by W. Timothy Gallwey — This was likely on your parent’s bookshelf when you were growing up. But this classic guide to the mental side of performance has held up well over time. Well worth the $10 paperback.  

READ: THE INNER GAME OF TENNIS →

Written from the American South.