Lost and Affluent

Ornella Hernández
8 min readMay 19, 2020
Miami Art Week 2019

Now that communities are slowly opening back up amid the COVID-19 pandemic, how society works and plays faces a new norm. From halted career plans to loved ones falling sick to relationship struggles, I wonder about the state of my fellow millennials — a generation already confronting mounting dissatisfaction with the current state of world affairs due to their complicated ambition. In this reflection, I focus on the pre-COVID experience of a specific sector of millennials: the privileged.

“I just felt like I needed to grow up,” he divulged about kicking his drug habit while in the back of an Uber on our way to a dinner date. I was shocked, proud and all the more attracted to him for it. I decided to believe him because I needed it to be true to justify my infatuation with him. It meant he was finally assuming his responsibilities as the heir to the family business and accepting those first-born son duties — a philosophy of biblical significance that has generationally dictated family dynamics. In theory, he could have chosen to follow his own path but ultimately, he chose to “set himself up for it,” according to his younger brother. He trained for it just like a prince or princess is groomed to take over a crown. It’s what was expected of him and it’s what he wanted — to carry on his family’s legacy while making his mark on the world. Well, don’t we all?

What you just read is my romanticized interpretation of events seen through the rose-colored glasses of a girl whose actual myopic deficiencies, mixed with rising levels of dopamine due to the aforementioned attraction, figuratively blinded her from clearly seeing the man in front of her (for the better part of a year) for what he truly is: a lost boy.

Like those from Disney’s Peter Pan, lost boys enjoy the freedoms of their wild way of life that Neverland offers. Similarly, my lost boy prefers to revel in the wiles of adolescent-like behavior when he isn’t working hard at his day job, because indulging in whatever feels good — drinking, drugs, chasing women — is easier than facing the pressure of measuring up to high expectations. This goes for women too. Lost girls and boys fuel each other. They choose to numb reality by blowing off steam together via lavish lifestyles resulting from indulgent upbringings where financial security was an afterthought complemented by seemingly boundless material possessions and educational/professional opportunities.

Neverland is a lifestyle — a bubble where affluence and glamour abound, and you’re too caught up in the pleasure, debauchery, immorality and vice to think about anything other. Neverland can be found all across the globe — from Manhattan’s Upper East Side to the South of France in the summertime to Singapore to name a few places. Its residents are privileged members of elite societies in which status and money transcend race and geography.

Think pop culture favorites like Gossip Girl, Crazy Rich Asians or HBO’s Succession. Its protagonists are individuals obsessed with social currency and the personal value he or she can add to their circles of influence — Who is invited to the charity gala? Who has the Art Basel party hook-up? Who will supply the drugs? Whose yacht will be in St. Barth’s next winter? It’s a fast life. Vanity and escapism are the priorities. Living in the moment and instant gratification are what matter most. Once you’re in, it’s hard to get out. As my mother, a New York City resident for 23 years, once so aptly described the Big Apple: “It’s like a lake of vanity. You dip your foot in and before you realize it, you are slowly dragged all the way in until it feels like ‘you can never leave’” (as the final song lyric in “Hotel California” by the Eagles goes).

Let’s take Gossip Girl’s it-girl Serena Van der Woodsen, a character whose presence and beauty captivates those around her but who also lacks direction and is often guided by her impulses in a constant effort to shed her “lost girl” ways in order to become a better person. Tellingly, in the show, her favorite book is F. Scott Fitzgerald’s The Beautiful and Damned, because “I relate to it more than I should admit,” confesses Serena in Season 4 (for fellow GG lovers). Fitzgerald describes his protagonist Gloria Gilbert’s normal state of mind as “existing each day for each day’s worth,” one that can arguably be used to describe Serena’s. The screenwriters’ choice to draw such striking parallels between Gloria and Serena speaks to a greater issue I’d like to comment on: generational malaise.

Malaise is a French word meaning discomfort or weakness, used mostly in reference to physical ill-being. Here, I apply it to the condition of millennials — a generation that is increasingly self-aware, in comparison to past generations, much to its own detriment. The main differences include parents, part of the baby-boomer generation, encouraging their millennial offspring to explore life by making the most of their twenties and pursue their passions because there is no rush to settle down. Traditional family values, however, suffer as a result. Women, who are motivated to be their own person and get married once they achieve financial independence, now face a world with lower rates of marriage and higher rates of divorce; higher rates of cohabitating with partners that may not result in a serious commitment; higher birth-rates of older women and high-risk pregnancies.

It is difficult to be at ease with the current state of world affairs — one that is marked by rising inequality, unaffordable college tuition (U.S.), political polarization exacerbated by the internet, social media and the climate and public health crises. Millennials, overall, feel disenchanted by whatever work we produce as it risks redundancy, irrelevance and/or failure. This malaise can lead us into a sort of mental paralysis that makes us question our life purpose and self-worth. This existential crisis of consciousness is coupled with constant pressure to enhance ourselves professionally. We are discontent with only one diploma or working for the same boss for long periods of time, while we stress the importance of earning a certain salary and achieving fame. If we do accept a job, it’s because it pays the rent and looks good on a résumé. Saving that money is another matter. We are always yearning for more — whatever “more” is. As the business landscape becomes increasingly lucrative and technologically-driven, we may be enticed by larger rewards. But we are no longer content to simply compete against the success of past generations, we want to surpass them. Why? We are around-the-clock connected to and attuned to social, political and economic issues. And that has led us into a state of chronic dissatisfaction.

Tying this back to my cohort of select millennials who prefer to be in Neverland, their generational malaise and the resulting sense of feeling lost is manifested very uniquely. Their penchant for decadence can be likened to that of the generation that reached adulthood during World War I — the Lost Generation. Their world that was marked by war resulted in a disillusionment and an unwillingness to settle for an ordinary life, chronicled by famous American authors and poets. Hence, the seemingly reckless and frivolous behavior of some Fitzgerald characters or those of his contemporary, Ernest Hemingway. Just like Serena van der Woodsen’s favorite book, mine also happens to be from this time period and for similar reasons: Hemingway’s The Sun Also Rises. Reading this tale as a 16-year-old Manhattan private-school girl, perhaps I interpreted it as a warning and have since been haunted by the character Robert Cohn’s words: “I can’t stand it to think my life is going so fast and I’m not really living it.” In the book, the OG Lost Generation felt their lives had no purpose or substance. As a result, they constantly traveled, partied and indulged in escapism tactics to diminish any feelings of impotency, akin to elite societies today who can afford to do the same with little consequence and for longer periods of time in their lives. In one of the novel’s scenes, Cohn expresses his fast life woes to fellow expatriate Jake Barnes who wisely concludes the conversation by stating that, “you can’t get away from yourself by moving from one place to another. There’s nothing to that.” He’s tried, he admits, but he learned from experience that insecurities or unhappiness cannot be fulfilled simply by changing locations.

Let’s illustrate this sentiment of “moving from one place to another” using another quotidian activity: going out. In my experience of city-life, on a night out in the town, I typically begin the evening at one club or bar and then bounce around to various other libation-stocked establishments before ending up at an after-party at someone’s apartment in the wee hours of the morning. The plan usually is described along the lines of: “We’ll meet up here and then join X here and then either go here or there depending on if it’s good or not and then…” Only God knows what “and then” will lead to and what adventures will take place on any given night out. However, there is something about these nocturnal plans that has never quite sat well with me, a feeling reminiscent of sheep herding. Sometimes I truly feel like I am one of the sheep or cattle following around the evening’s self-designated leader to the next destination. And these decisions to migrate from lounge to after-party to another after-party can happen at a moment’s notice so it’s best to keep up if one wants to continue the party. And it’s very easy to get left behind and be left to fend for oneself. As my friend once explained, “girls have to wear sneakers or comfortable shoes just to keep up and not pull a Cinderella. It’s all about being at the next thing.”

However problematic this analogy and however trendy your platform sneakers, the idea that “you can’t get away from yourself” or reality no matter how many cities you move to, parties you go to or crowds you mingle with, rings true. So why do we even try? A lost boy or girl with a work hard, play hard mentality may believe he or she deserves “fun” as a reward for any work put into their professional endeavors. Maybe peer pressure regarding expectations plays a role, or they follow along simply out of boredom and a lack of sense of consequence. Or perhaps it is a habit that is just too hard to break. Most ambitious millennials share an eagerness to make our names known and be remembered, perhaps intensified by a rising need for external validation as a result of social media. However, what may differentiate how the general millennial generation (and increasingly Gen-Z) manifests its need for self-adulation from that of the elite population is mainly due to the latter’s distinct viewpoint: the elite never accepts ‘no’ for an answer and success means always finding a way to get your way. Whether you choose to live up to your family’s vision for you or choose to prove your worth in the world separate from a last name or legacy, failure is a relative term when you know you may have a ‘plan b’ or inheritance to fall back on. That’s not an excuse, however, to be mediocre. As a result, success is directly attributed to how you deal with any internal and/or external pressure of measuring up to those high expectations, whatever those may be for you.

In regards to my lost boy at the beginning of this reflection, we did not end up becoming boyfriend/girlfriend, and his “growing up,” professionally speaking, was interrupted by COVID-19. However, his desire for personal redemption, a common theme among fellow lost boys and girls, remains strong.

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