3 Lessons I Learned During My Time Undercover as a Wealthy Chicagoan
I am not a wealthy Chicagoan. I’m a second-year law student still paying off medical debt from 2019. But through a series of fortunate events and strategic use of my student status, I had the opportunity to briefly experience life from the rose-colored, Chanel-clad eyes of someone in a vastly different tax bracket, starting with a membership at one of the most exclusive social clubs in the city. Due to a health emergency and reassessment of my priorities, not to mention the crushing reality of my spring semester tuition invoice, my high-end lifestyle was destined to last no longer than the length of my winter break, but the lessons I learned will last a lifetime. Here are some insights I gathered from this beautiful-yet-fleeting moment of my life:
The barrier to entry is surprisingly low.
In order to get accepted as a member of the Union League Club of Chicago (ULCC), I had to submit an initial application, take an in-person tour of the club, have a formal interview with a member of the admissions board, submit another application, and have those applications reviewed by said board. The whole process from start to finish took under two weeks, and the questions were very straightforward: why did I want to become a member, what activities did I see myself doing, what contributions could I make to the club’s various charitable organizations, etcetera. I was repeatedly sold on the “young members committee,” which purported to be several hundred members strong, with multiple outings scheduled throughout the month (I later discovered that nearly all of these outings centered around alcohol, which was completely unappealing to me and therefore I never took advantage). Once I became a member, I had access to one of the largest private art collections in Chicago – the ULCC is sometimes referred to as the “other Art Institute” for this reason. Discounts and amenities abounded: a private gym with personal training priced at less than half the rate of the leading fitness centers, an enormous pool, multiple private pickleball courts, a library that resembles something out of Hogwarts, massively discounted hotel rooms and dining experiences, access to $30 lobster dinners once a week, a cigar bar, an onsite salon, and so much more. That’s to say nothing of the networking opportunities, which I had originally cited as my top reason for joining. The final bill for one month of access to all this? Less than $250.
Physically getting into a “rich people” environment isn’t all that difficult if you can “walk the walk and talk the talk,” as they say, especially in a city like Chicago where all the wealthiest individuals dress in deceptively expensive jeans and t-shirts. A blowout from Drybar is $50 and a quick at-home manicure is $20. Target has knockoff Burberry and Gucci brands, and if you can finagle your way through a conversation about NFTs, you’ll have everyone believing you’re just as New Money as they are.
Belonging often exists in a vacuum.
One question I repeatedly asked during my ULCC interview was whether there were programs designed to diversify the membership pool. I’m a white, blonde, 20-something, so I fit in just fine with most suburban circles, but one of the reasons I moved back to Chicago from LA was the fact that I hated living in a bubble. I didn’t want to just assign a certain percentage of my membership dues to ULCC’s partnership orgs and pat myself on the back for a societal duty fulfilled, I wanted to speak with real people and learn how I could be a better advocate and ally. Unsurprisingly, however, the overwhelming majority of members are middle-aged white men. I did expect to see one or two people from non-white backgrounds, but every single time I stepped foot in the club, the only people of color there were the staff. It felt very much like I had wandered into an 18th-century plantation, and I found myself questioning whether I even wanted to be seen there. The irony was not lost on me: I had spent so long worrying I’d stick out like a sore thumb and that the upper-class crowd would know I’m not “one of them,” but the reality is that as a member, I very much was – I’m privileged, white, wealthy-passing, and I was happy to sit in an exclusive cafe sipping a $12 chai while the only black person in the room stood silently at his post awaiting his next order. It was an environment in which I knew no one would question my belonging, but it was a wake-up call when I found myself wishing I’d fit in just a little less. I remember fixing my hair in a gold-plated mirror and thinking to myself, “oh god, I’m insufferable!”
I had a similar sinking sensation when I had the opportunity to dine at Nobu with my sister. She and I opted for the Chef Nobu Special, which is a uniquely-curated experience starting at a measly $150 per person. The price per person goes up from there, with higher tiers broaching $1,200 and consisting of rare caviar and A5 kobe beef. We were asked to give a few parameters: any allergies or restrictions, anything that particularly caught our eyes, and whether we wanted to include drink pairings with each course. Some of the courses were off-menu specialties, favorites of the chef or experimental dishes usually reserved for adventurous diners.
I have to admit that this was, bar none, the best meal I have ever had in my life. The food was so good that our server had tattoos of some of the dishes, and apparently rapper Drake shouts out Nobu in one of his songs. I can’t blame him – the experience from start to finish was impeccable. I even saved the receipt so I could remember how lucky I was – and am. But I was frustrated to see that the majority of diners didn’t seem as giddy as we were to be there. My sister and I had been looking forward to this dinner for months and had saved up every penny we possibly could. When we arrived, we could barely contain our excitement, and my sister fretted that she wasn’t dressed elegantly enough. Looking around, though, we saw multiple tables of men wearing backwards baseball caps, jeans, and t-shirts with stretched-out necklines. A mother-daughter pair seated near us had clearly picked this place as a last-minute option after a day of running errands. Many people were on their phones the entire meal, barely looking at the $80 wagyu gyoza in front of them. We admired the care and thoughtfulness that was clearly imbued within each hand-crafted dish and took our time to appreciate everything in front of us. But to so many other diners, this was just Thursday.
At first, we were appalled – how could anyone be so blind as to take for granted this once-in-a-lifetime opportunity? But then we realized that luxury isn’t a tourist industry; it doesn’t exist for struggling grad students like us who pull couches apart looking for loose change, it exists for C-Suites and dealmakers whose way of life is perpetually elevated. No one was looking at us in an accusatory way or hovering over us to ensure we didn’t dine and dash. No matter how much we insisted that this was a truly special occasion, and one we probably would never be able to afford again, the reality was that we were in the same room as everyone else, enjoying the same food, paying the same market prices. We belonged there because we were there. Somehow, this truth offered nothing but discomfort.
There’s no way to project to the rest of the room that you’re genuinely interested in the preservation of sanctity when it comes to experiencing luxury. When you’re in a glass house, the prisms of reflective light will bathe your face in rainbows regardless of whether you enjoy the sun. When it comes to wealthy circles, at least the ones I temporarily entered, money was social currency as well as actual currency. If you could afford to even consider dining at a Michelin-starred restaurant, then you were welcomed there. I’d like to point out that people of color are treated with far more scrutiny and skepticism than their white counterparts in these spaces, but there are far better sources and stories about that by people who have actually experienced it. My personal experience, with all my privilege, can be summed up thusly: wherever you go, there you are, even if you don’t feel like you deserve it.
Money can’t buy you class.
There exists a notion that wealth is usually intertwined with etiquette. “Old money,” for example, conjures images of large intergenerational estates where families take great care to maintain an illusion of propriety and education. Ladies cross their ankles, not their legs. Men wear ties and remove their hats indoors. “Please” and “thank you” punctuate each sentence, and everyone takes pride in having excellent manners.
What a joke.
Many people blame the influx of Californians to Chicago as the source of abundant shamelessness and impoliteness in traditionally exclusive spaces, and as an ex-Californian I can understand that sentiment, but my experience revealed a much uglier truth: because extreme privilege often shields people from consequences, egregious displays of wealth sometimes beget egregious displays of rudeness. I witnessed a middle-aged, impeccably-dressed woman in the ULCC cafe spread her belongings across several tables and chairs, prop up her iPad and phone like a NASA control center around her, and proceed to watch TikToks for over an hour with the sound turned up. Another woman stood in the middle of the room at a highboy table, drink in hand at 2:30pm, and openly scolded her business partner about a highly confidential financial agreement. On more than one occasion, I heard the phrase “don’t clean that up, it’s the staff’s job to do that for you.” The 18-year double-cask whiskey on the rocks is too cold. That person experiencing homelessness has the gall to stand within 30 feet of this building. The $260 bluefin tuna is too salty. Beach too sandy; water too wet.
Be that a lack of gratitude or self-awareness, the impact it left on me will forever remain negative. I think back to the sanctity of scarcity and the value I project onto others’ wealth. I could never tell someone how to spend their money, but I found that the culture around wealth can be so isolating and downright boring. How can it be that something so highly sought-after is so disappointing? Is that a reality that everyone faces when they reach a certain level of success? Or are there still precious experiences in the world reserved for those who can not only enjoy them, not only appreciate them, but desire to share them?
In the $32 Uber ride back to my studio apartment with the broken sink and temperamental radiator, I let down my hair and pulled off my fake eyelashes. Inside that apartment awaited the lounge pants I’ve had since 8th grade and a t-shirt with a mysterious stain that has defied dozens of aggressive spin cycles. It’ll be packaged ramen and generic-brand Walgreens hauls for the foreseeable future, but it was worth it to find this peace: The gift of low expectations pays dividends in the form of pleasant surprises. Perhaps the fur-lined lap of luxury is a nice place to lay my head, but I now know that middle-class mediocrity is my sanctuary.