27

When I turned 26 last October, we clinked our glasses at dinner to “new adventures.” If you knew me at the time, you knew that “new adventures” was code for, “my life was just completely turned upside down and the only thing keeping me from a nervous breakdown is the thought of a giant roasted chicken with a pureed potato coming out on a platter in 15 minutes.”

A month before I turned 26 — after nearly four years in New York City — I’d accepted and started a job with Google in San Francisco. I didn’t have an apartment there, so I was living out of Airbnb rentals while I kept my apartment on the Upper East Side. I’d planned on moving back after a year, but that was complicated: I didn’t know if my job would allow me to return and work remotely; I couldn’t afford to pay for two apartments for an entire year; and I didn’t know whether or not I’d like San Francisco. Not to mention, I’d just started dating Brendan, who (conveniently) lived in New York City. I was behind on my New York rent, making biweekly trips back to the east coast, and finally “settled” into a four-month San Francisco sublet that was a twin bed in a walk-in closet. But I was hell-bent on making all of it work: [Carrie Bradshaw voice] the new job, the new relationship, the New York, the new San Francisco.

A year, four apartments, two cross-country moves and two jobs later, here we are. If you’re thinking, “Wow, I wonder if convoluting his Instagram presence like that gave him even more gray hairs,” the answer is yes — yes, it did. I moved out of my New York apartment in the spring and moved out of my twin-bed sublet in San Francisco the next day. For the month of March I was in limbo between hotels, Airbnbs and couches with two massive suitcases living under my desk. In April I moved into a wonderful apartment that I’d stay in for the remainder of my time in San Francisco. In September, I moved back to New York for a new role at Google and moved in with Brendan in Chelsea. I’ve aged ten years since I started typing that.

It was a year that forced me to ask myself hard questions and put my world on a chopping block. Every decision seemed impossible: should I take this job and upend my life? (Yes.) Should I let go of my apartment? (Yes.) Should I stay in San Francisco solely for a job? (No.) Should I commit to moving back to New York and potentially give up a career at Google? (Yes, because you’ll do your job well and it will give you options.) Is Donald Trump actually the Republican nominee, or am I just in a coma? (Find a new therapist.)

There were many moments when my self-doubt crippled me. My whole life leading up to my move to San Francisco felt like a chain of “right” decisions, and there I was with a bunch of big questions I’d just created for myself and none of them had right or wrong answers. I was one of those Millennial think-pieces that ends with a blanket statement about how this generation ruins everything because we were coddled. Or something.

A day into 27, I think my decisions were the right ones. If we were at brunch talking about it, I’d probably say, “I never do this!” before saying I’m proud of myself. But I am proud of myself. I took a big risk, worked really hard, survived the Great Logistical Nightmare of 2016, and the risk paid off. So on this birthday, I’m grateful for the tough decisions — the ones that keep you up at night, take you out of your comfort zone, and yes, give you a few more gray hairs — because those are the decisions that help make “to new adventures” more than a silly glass-clink.

This post is dedicated to my Uncle Alan, who helped me believe in my hustle. Rest in peace, UA. I love you and miss you.