What a Trip to Aspen Taught Me About the Wealthy

Posted Friday at 09:00 AM5 days

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You can smell Aspen before you see it. Not the pines or the crisp mountain air, but the signature hotel scents — bergamot, cedarwood, a whiff of oud diffused into lobbies where bellboys wear Rolexes under their white gloves. A hundred-dollar cocktail arrives at your table like an accessory, complete with a gold flake balanced on the ice. Bottega and Gucci bags outnumber the mountain-themed souvenirs. Men drape cashmere over their shoulders like they were born into it. Women glide past with Pilates legs and Botox-polished faces that carry no pores, no wrinkles, no margin for error.

It’s indulgence, yes — but indulgence is only the backdrop.

The real story here is the current running beneath it all: comparison.

Walk the cobblestone streets and you’ll see cowboy hats worn with Italian loafers, fur coats sharing patios with denim jackets, art galleries tucked between ski shops. The town is eclectic, a blend of ranch and runway, but the common thread is the sideways glance. Everyone is noticing. Everyone is cataloging.

It’s not judgment in the sneering sense. No one here is muttering about who is beneath them. It’s subtler, almost invisible. The energy is less they don’t belong and more do I?

The gaze lingers just a beat too long on someone else’s watch, bag, or boots. It’s the quick calculation of where you rank in a room where everyone is already extraordinary. The quiet hum of one-upping, not with cruelty but with insecurity.

What is it about wealth that requires constant vigilance? Getting there isn’t enough — you must stay there. Hold your ground. Keep climbing a mountain where the summit keeps shifting.

A cashmere sweater is no longer warmth, it’s armor. A luxury watch isn’t about time, it’s about status. Even the laughter at dinner tables can feel just a little too loud, as if to cover the nerves about whether you measure up.

And the strangest part? The same people who already “have it all” still seem to carry the weight of asking: Am I enough here?

Aspen simply magnifies what all of us feel in quieter ways.

In the suburbs, it’s not a Bottega bag — it’s the granite kitchen island.

It’s not a Rolex — it’s the SUV in the carpool lane.

It’s not a $100 cocktail — it’s the latte in the reusable tumbler that proves you’re eco-conscious and stylish.

At work, it’s who gets cc’d on the important emails.

At church, it’s who volunteers most visibly.

On social media, it’s who booked the “right” kind of vacation or hit the milestones in the “right” order.

Different costumes, same theater. We are all taking inventory. We are all glancing sideways.

Aspen reveals a truth most of us already know but rarely say out loud: comparison doesn’t vanish with success. It scales with it.

The middle-class mom comparing her Target sandals to another mom’s Tory Burch flats is no different from the Aspen skier comparing her Gucci puffer to someone else’s Fendi one. The stakes feel higher, but the human ache is the same.

It’s the quiet, restless question humming underneath: Am I better? Am I enough? Do I stand out here?

And maybe that’s the most decadent indulgence of all — the belief that being “on top” will finally silence that question, when in reality, it only amplifies it.

As I walked through town, it struck me that the mountain itself doesn’t notice. The aspens whisper in the same wind, the snow falls indifferently, the peaks stand tall whether a man drapes cashmere over his shoulders or a tourist buys a beanie from a souvenir shop.

The mountain doesn’t keep score. Only we do.

Maybe Aspen is less about wealth and more about the mirror it holds up to the rest of us. A reminder that comparison is the most democratic sport there is — played in penthouses and cul-de-sacs alike.

And maybe the truest freedom isn’t climbing higher, but learning, finally, to stop looking sideways.

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This post was previously published on medium.com.