I Have Some Regrets

Soon, it will be time for me to leave New York. This isn't how I thought I'd say goodbye.

Lauren Conrad cries in an episode of The Hills. Image via MTV.

I hate people who say they have no regrets. They are liars. I know they’re not immune to replaying arguments in their heads while showering, finally finding the exact words that would have shut their opponent down. Why didn’t I think to say that in the moment?, they ask themselves. That is a regret! Let’s be honest with ourselves here. 

Lately, I have been haunted by my own regrets. Despite my best efforts to convince him otherwise, my fiancé, Darien, has accepted a new job. In Los Angeles. In this economy? you might ask, but he’s an ER doctor, and those happen to be in quite high demand right now. Magazine editors, on the other hand, are not so much in high demand, which means I have precious little bargaining power. So, we’re moving across the country in the middle of a pandemic in just about a month’s time. My first regret is that I ever thought I could be an “LA person” when this opportunity arose. My second is buying a new winter coat in January, convincing myself of its “cost-per-wear” potential. 

Now that I’m leaving, I am suddenly wistful for every little thing in New York. There are the obvious things I’ll miss, like the bagels and the pizza and the way the buildings gleam when the sun sets. Not to mention the accents and the traffic noises and that surreal moment when the leaves turn in fall and everything feels like a movie. For the past two weeks, I’ve been reminiscing about every magic moment I’ve had in New York over the past ten years, all while Darien begs me to stop procrastinating on apartment hunting. I tell him I’ll get to it—just after I go for a quick walk outside. Unfortunately for him, New York is showing off lately, even while its residents hide away. The cherry blossoms are blooming, lining the streets of Brooklyn in clouds of pink, and birds chirp happily in their branches, gleeful that their songs can finally be heard. I regret that it has taken me this long to truly appreciate the beauty of New York. 

Even more, I regret that I ever fooled myself into thinking I could “conquer” New York. My best career advice (thank you for asking) is: Don’t do what I did. I enrolled at NYU with the express purpose of landing a job in magazines, so I immediately nabbed an internship at Condé Nast and stayed for three years, hopping between editorial departments. I was so excited to go to work that I crammed my class schedule and managed to graduate a year early, all in an effort to land my first job in publishing. This is my fifth regret: I should have stayed in school and spent more time enjoying what college had to offer. I even skipped my own graduation, convincing my parents to let me take a week-long trip to Paris instead. If you thought this was my sixth regret, you would be wrong. Lauren Conrad was right: Always choose Paris. 

I never really let myself relax. Landing one job was never enough—I had to be the best. Just like I rushed through college, I was determined to climb the career ladder at breakneck speed. Somehow, I had gone from assistant to editorial director of Teen Vogue in three years’ time. I would like to think that I got there based on merits alone, but I now know better: it was a mix of hard work, dumb luck, and a lot of privilege. I regret that I wasn’t able to acknowledge this hard truth a lot sooner. 

My best career advice (thank you for asking) is: Don’t do what I did.

The good news is that I was never one to rest on my laurels. If I didn’t have something to prove to the world, I always had something to prove to myself. My ferocious ambition was also a bottomless pit, and no matter how hard I worked, I worried that I would be revealed as an impostor. I was too young, I thought, or not smart enough. In the halls of Condé Nast, I suddenly felt not well-dressed enough, not attractive enough, not Ivy League enough. I’ll show them, I reasoned. I poured myself into my work, starting my days at 7AM and often arriving home at 10 or 11PM. More often than not, I ate breakfast, lunch, and dinner in my own office. I even went to work on the weekends, where my only company was the security staff. The lights would automatically turn off every hour or so, and I’d have to go into the hallway and do jumping jacks to make the motion sensor turn them all back on. Darien joked that I worked longer hours than he did as a second-year medical resident, but then we actually tallied our hours and realized he was right. My seventh regret is not taking this as a warning sign, and instead wearing it as a badge of honor. 

The emotional toll of overworking was all made clear to me one night. I had just launched them, Condé’s first LGBTQ+ brand in its 125+ year history. To commemorate the occasion, One World Trade Center lit up in the colors of the rainbow. One would think that I’d be awestruck by this moment: I helped to make a mark on New York City’s skyline, on the most important building in the cityscape. Despite my success and all the friendships I’d made over the years, the only person I could find to come watch the building light up with me was one of my coworkers, who agreed to accompany me for a short time before leaving to eat dinner with her family. When I got home, Darien wasn’t speaking to me. I had forgotten to tell him about the event. He had wanted to be there to share in the moment, and I ended up going with someone who didn’t really want to be there. My eighth regret came when I woke up the next morning and realized that even with all the success I had ever dreamed of, I still felt so alone. 

For legal reasons, it is too soon to share my multitude of regrets from my too-brief tenure at Out Magazine. As anyone with even cursory knowledge of the situation might imagine, I have many. I will say this, though: I do not regret taking the job, and I’m proud of the work we did there. I hold a special place in my heart for the people who worked and still work at the company. The biggest regret I can share is that I was both arrogant and naïve enough to believe that I could “save” the publication. When the time finally came to offer myself and my salary for the chopping block—presumably to delay layoffs for my staff—I did so in a fit of laughter. The CEO looked at me with concern, and asked what was so funny. I couldn’t answer, so I kept laughing. Later that night, the laughter turned into tears. I sat against the front door of my apartment for hours, sobbing on and off again, whispering and yelling, “Oh my God.” My ninth regret is that I interpreted the brand’s inevitable failure as one of my own making. 


This brings me to my tenth regret. Ten feels like a really nice number to end on, but I could keep going. There are a few others tucked in between these bigger moments—that I wore an Apple Watch on the red carpet of the Met Gala, that I shook Donald Trump’s hand after he’d won the election, that I spent an absurd amount of money on clothing to impress my peers and my boss—but they all more or less feed this final point: I regret that I spent most of my time obsessed with fulfilling my wide-eyed, New York City dreams without realizing that they weren’t making me happy at all. The city whizzed by me in a blur as I sat in the backseat of too many cabs, my neck craned downwards as I answered emails or Slack messages on my phone. (Actually, this is my eleventh regret: downloading Slack.) My friends became acquaintances, our relationships dissolving into Instagram likes and the occasional pledge to “see each other when everything calms down!” More than once, I almost called it quits with the man I love, because he was too tired of waiting for me to care about him as much as I cared about my job. 

Ironically, by the time I had finally licked my wounds from being laid off and found myself ready to re-emerge in New York, become a better friend, go on romantic dates with my fiancé, and see the art I’d been missing for so long, New York City closed her doors. It became dangerous to go outside, to be around other people. Darien and I will be leaving for Los Angeles without being able to hug our loved ones goodbye, or eat dinner at the restaurant where we first met, or visit the museum that became our favorite date destination. Instead, I’m sitting on my couch, watching the sun rise and set on the city I took for granted for ten years. Eventually, I will do so for the very last time in a good, long while. This seems only fitting: In bidding farewell, I realize I never deserved New York after all.