On Letting (Yourself) Go

An Absolutely Necessary Didion-Inspired Goodbye to New York City

A portrait of the artist saying goodbye to all that.

At 22 — or any age, really — there is nothing more promising or terrifying than a one-way ticket to The Rest of Your Life. As I clutched mine from Houston to New York in 2006, I tried to let go of any fears or self-doubt as we approached LaGuardia, channeling that restless energy into silly, Bradshaw-esque fantasies of how a life in Manhattan could, should and would unfold and flourish over time, and how long I’d be able to survive and thrive in The Center of the Universe. I took off for New York City, both intrepidly and trepidatiously, just days after graduating from college, itching to start from scratch in a land of newness and promises, desperate to make this tiny, magical, challenging island my home. Manhattan was IT. The top. The pinnacle of success. The only way, I thought, to feel like I’d made the most of this big little life. The profundity and excitement of sheer possibility made it easy to leave everything I’d ever known behind, to not overthink the outcome, to just let myself…go.

***

But making the city feel like “home” didn’t come without a series of real-estate trials (and occasionally, errors). The first few years were a mixed-bag of sitcom-worthy apartment-hopping adventures. I spent my very first week in New York with my dad’s longtime friend in his sprawling TriBeCa loft, sleeping in an actual treehouse bunkbed while the kids were away at camp; the next three months were spent with a kooky, sixty-something playwright in her creaky, but charming East Village apartment; then, a few weeks with my Upper Eastside cousin in her luxury skyscraper; the next six months on 9th Street with a girl I met in the housing section of Craigslist who had a manic Pomeranian and a manic personality; two years in a three-bedroom, fifth-floor walk-up on 52nd with death-defying loft beds and agreeable, like-minded roommates; a year in a railroad-style Hell’s Kitchen gem with a stellar view of the Midtown skyline and a tumultuous relationship with a spiteful feline; and, up until this very moment, eight years in a rent-controlled studio with adoring doormen and enough room for all my books and records and memories, a place that finally — finally — made New York feel like home. It was easy to let go and grow out of each of those urban nests as my expectations, salaries and need for personal space evolved. But not 2F. 2F is where I’m typing this right now, the laptop keys echoing amid the emptiness, on my very last night in the city. This one was hard to let go.

***

My big-city career dreams were grandiose and modest all at once: to land a job in “words.” Writing, editing––I’d do it in any capacity if it meant getting to play with the English language in exchange for money and dental insurance. I had one job interview lined up upon arriving in New York that summer – it was with an executive editor at Abrams Books, a well-known publisher in Chelsea, and I was offered the $8/hour editorial internship on the spot. If I was going to pursue the precarious path of past and present logophiles, I’d need to let go of any notion that I’d be paid my subjective worth (for the time being, at least). After the internship, I took an editorial assistant job at the Social Services Employees Union on Broadway, writing stories for a large, close-knit family of union workers, and reporting to a Larry David-ish editor who genuinely thought you “goggled” things instead of “googling” them. That role was short-lived, and my next prodigious pursuit was accepting an offer as an assistant editor at a small children’s publisher in Midtown. That five-year journey is teeming with unbelievable and unforgettable experiences and career curveballs, but most importantly, it led to: a promotion to senior editor, four forever friends, and several face-to-face meetings with the infamous Lisa Frank. In 2012, it was time to move on from the world of activity books and beloved cartoon characters, and so a friend sent my resume and Twitter handle to an editor at MTV who was hiring a freelance copywriter. I distinctly remember him saying, “I love your tweets,” and the job was mine if I wanted it. The Best Contract Gig Ever lasted about nine months (eight months longer than expected), and it took the entire bleak winter season to find something remotely comparable. Early 2013 is when the sun started to shine again, and I became the copywriter at JetBlue — an extraordinary plot twist in my career — and for the next three and a half years, I proudly rounded out my portfolio, honed my (air)craft, met lifetime loves and traveled the world and back. And when a new opportunity appeared in 2016 — to develop the brand voice for the newest CBS streaming platform — I jumped at the chance to be back in the entertainment industry, rubbing elbows (consensually) with show-business greats. To be both frank and vague, some of those jobs were easier to let go of than others, but they all added value to my career as a professional writer––a writer who is beyond ready for her next great creative challenge.

***

Over the last twelve years, I’ve been to a hundred going-away parties — those who’ve had enough of the city sacrifices, ones who are ready to experience the world through a different lens and redefine “normalcy,” ones who can’t wait to just let it all go. I never understood it, but I respected it. People come and go so often in New York, that I feel lucky to have met and loved some of the very best — many who have stayed, even more who have gone — but I’ve learned when to hang on tight to the Forever Friends, even when they’re no longer a subway stop or Uber ride away. I’ve met the most incredible people by forcing myself to inch out of my comfort zone — at work, through family, through friends, at bars, at parties, by pure chance, and I’ve made an effort to keep the crucial ones close. I’ve also learned when to let the lousy ones go. Sometimes it feels like a relief, and sometimes it (still) feels like a missing puzzle piece. I’m an only child, and I’m single — friends are my family. And I’m sad to be leaving tiny pieces of my heart on avenues across boroughs.

***

To All the Boys I Barely Liked Before: thank you for all the first dates during my time in New York. Some of you even got second and third dates, a select few even got more than three, and one took up like, 16% of my time here. Give or take a rare bout of self-pity, dating in NYC has mostly been pure and utter joy because I’ve never taken the act seriously enough to be devastated by it. I’ve swiped through every app, I’ve been in Time Out New York’s Dating Issue (twice!), I’ve speed-dated, I’ve slow-dated, I’ve kissed strangers, I’ve been on blind dates, I’ve been on bland dates, I’ve documented my dates in real time, I’ve had men write about me in essays, I’ve let good ones go, and good ones have let me go, I’ve opened myself up, I’ve shut myself right back down, and I’ve felt a million butterflies, many of which I misidentified as a vodka buzz. My dating life has been plentiful and FUN and weird and wild and I’m proud of myself for all the dates I let myself go on. Too many, maybe. But just enough to know exactly what I want and need in a partner — when all the stars align, of course. (Good thing you can actually see the stars in the Pacific Northwest.)

***

The best and most important thing to transform during this lengthy time in New York is, without a doubt, my writing. After years and years of simply documenting my life on Tumblr (like an emo teenager), I finally began to take new risks, somewhere around 2012 — submitting essays, writing a screenplay, self-publishing a novella, writing comedy spec scripts, applying to creative programs, submitting funny pieces to McSweeney’s and The New Yorker, tweeting with mild abandon. I let go of the fear of rejection and put myself out there —like, really out there––hoping, at the very least, to hear that people liked what I had to say. My writerly confidence has grown a million percent in the last two years alone, just from sharing bursts of wit with the world (but don’t worry, I’m still plagued with self-doubt, like any good writer!). I moved to New York to collect stories and to share them, to be inspired by the energy, to let my city escapades serve as a muse, and boy, have they. But that energy and those escapades have also kept me from writing. I’ve let thousands of hours of writing time fall to the wayside to go out and live the stories instead. I have so much more to say, and the right words to say it, and only a fool would let that go.

***

If you’re doing it right, New York, in theory, is supposed to make you feel a little uncomfortable from time to time — not in a creepy way, but in a way that reminds you to push harder, try new things, surprise yourself, stay on your tippy toes — never settle for idleness. I’ve curated a life that has rarely stood still, but at some tragic point, I became too comfortable. Nothing in New York felt new. This, my friends, is how I knew it was okay to let go.

New York is a city of contradictions, and I love that about it. There is so much beauty in the mundanity, like the casual reflection of the Empire State Building in a filthy puddle. My relationship with Manhattan has been both extraordinary and ordinary, hopeful and discouraging, delicate and gritty, fabulous and familiar, and I couldn’t imagine spending my twenties and early thirties amid any other backdrop. Those 4,504 days and nights are not just a string of stories and adventures and amusing anecdotes, they are my life––a life I made from nothing, so that I could eventually make it anywhere.

I still can’t think of a life outside of New York City, even though I’m embarking on a new one this week. This doesn’t take away from the utter thrill and excitement of my new Seattle endeavor, it only emphasizes the sizable and unyielding belonging I feel to this city. To quote the inimitable Joan Didion, “…quite simply, I was in love with New York. I do not mean ‘love’ in any colloquial way, I mean that I was in love with the city, the way you love the first person who ever touches you and you never love anyone quite that way again.” New York has made me stronger, more creative, more confident, more empathetic than I ever thought possible. I am grateful for every glass of champagne, every rooftop, every sunset over the Hudson, every book I’ve read in Central Park, every kiss in a dark bar, every afternoon wandering museum halls, every unbelievable celebrity encounter, every friend I’ve ever laughed with, every friend I’ve cried with, every picture I’ve snapped, every time I’ve pretended to be starring in my own rom-com, every ounce of pure luck, every hour of hard work, every cherry blossom in the spring, every ‘grammable dead leaf in the fall, every twinkle of the ESB, every word I’ve written, every ephemeral moment that could only happen in New York.

***

Seattle is not New York. And I know that; they are not to be compared. They are separate chapters — different books even. There will be great apartments, great friends, great boys, great words, great jobs — or maybe there won’t. But I will give this part of my life everything I gave New York, and more.

At 34 — or any age, really — there is nothing more promising or terrifying than a one-way ticket to The Rest of Your Life. The profundity and excitement of sheer possibility makes it easy to leave everything I know behind, to not overthink the outcome, to just let myself…go.

So.

Let’s go.