Some thoughts on New York.

1. My earliest vivid memory of New York is walking through The Gates in Central Park. It was the winter of fourth grade, halfway through my first year at a new all-boys middle school that required I add a Brooks Brothers Boys blazer and zip-up ties to my wardrobe. A new friend invited me on a weekend trip to “the city”. His parents said The Gates installation — thousands of large two-legged orange flags erected throughout the park — was a big deal. I didn’t really “get it”, but was thrilled to be there nonetheless. Near the end of our walk through the park, my friend's father chided me; I had let slip too loud that he’d been accumulating dozens of the one-per-visitor fabric memorabilia from every attendant we’d seen.

2. I have moved to New York three times in my life. The first move was preceded by three falling dominoes.

3. First: I started watching Girls. Sophomore year of high school, often in the music building during free periods via torrents traded with a friend. Before Girls I had never considered the concept of "Bushwick" or that a warehouse might be a suitable place to host a party (let alone a desirable one). I had also never, in the midst of my rigid New England prep schooling, considered that a life of stumbles and detours and general lack of direction might be so alluring. The show flipped some chemicals in my brain that I believe have never since flipped back. In junior year when my therapist asked me if I ever had suicidal thoughts, I’d say "sometimes" but then caveat, "if I ever decided to kill myself, I would first run away to see what living in New York was like. Only if that didn't work would I proceed". Which was the honest truth.

4. Second: two months before I was set to start college, my parents brought me down to the basement and informed me, between apologies, that I wouldn’t be headed to Philly that fall. For “financial reasons” I didn’t quite grok. I nodded, trying to project nonchalance. Later, through tears, I looked across my bedroom and saw a copy of the Steve Jobs biography on my bookshelf. I remembered him being suddenly ousted from Apple by the board and decided in that moment (this is true) that, like Steve, I would succeed and look back on this as "the best thing that ever happened to me". One of my biggest fears about getting older is becoming less corny. Sometimes it is a necessary way to be.

5. Third: I secured a three month internship at a budding design agency in Dumbo that focused on early-stage startup branding. I bested a couple college students for the gig. Thanks to a handing-out-business-cards kind of hustle I no longer believe I possess, I also secured the option to do design work for a Boston-area startup while living at home. The decision was easy. If you ever get the chance to move to the city whose very existence stops you from killing yourself, I recommend you go.

6. While catching up with my fourth grade “The Gates” friend, I learned he was also taking a gap year, also headed for New York, also for an internship, also in Dumbo. A small theater company, he said. Only near the end of the call did we realize we would be working in the exact same office building on Jay Street. I freaked at the coincidence, but he reacted as if it wasn’t that big a deal. As if this was just the kind of thing that I should expect to happen in this city.

7. My mother didn’t believe the company was a real company. I showed her the agency's website, the one I spent hours ogling. A wide open office layout, dogs at work, "sometimes even yoga", leather couches, mood boards pinned to the walls… all novel and beyond cool to eighteen-year-old me. "But anyone can make a website," my mother retorted. So we drove to Brooklyn and, on the fourth floor of an industrial office building, found a metal door with the Company Name printed across the front. We couldn’t go in (it was Sunday, thankfully), but seeing the door was sufficient for my mother.

8. A few days into my internship, I joined some designers for happy hour. My first time at a bar for drinks. What a life! A couple sips of beer evaporated any facade of chill and I started asking everyone what it felt like to work a dream job at such a cool company. Everyone glanced at each other and, in turns, told me they were underpaid, always rushed, and stuck with clients with bad taste who always chose the wrong direction and implemented their logos on shitty websites. Turnover was high, they said. They would probably leave in the next year or two, they agreed. I nodded as if my image of life’s possibilities wasn’t crumbling inside. The conversation quickly moved on. One designer, who had spoken a few moments earlier about the pleasures of being choked during sex, said her dream gig was to design terrible looking graphics for a local weather station. I stayed quiet the rest of the night. There was too much I didn't understand.

9. (For years, I retold these gripes to anyone who asked about the agency, thinking they were unique or indicative of the company’s potential. This was, of course, a naiveté even greater than my original).

10. I am writing this from New York though I don’t live here anymore. When someone asks why I’ve come for the month I allude to work, but that’s not true. It’s just simpler than explaining that I’m working through the answer to that question myself in an upcoming numbered essay.

11. I wasn't allowed to live in Brooklyn.

12. My first New York apartment was a six-week sublet with two bunk beds and four guys stuffed into one bedroom in SoHo. I had the top right mattress. The ladder was metal and creaked. My roommates were real adults with real jobs. One of them worked in consulting, another said he “didn’t mind” the mouse. The location was great.

13. Leading up to my time in the city my father kept repeating, "if you can make it in New York you can make it anywhere". He would know, I thought. He had made it in the city much younger than I, immigrating from Seoul to Queens in middle school. Whenever he walked over a subway grate he inhaled deeply and talked of missing the smell. He told stories of running around the city alone with a roll of quarters in his pocket for safety.

14. My first time drunk in New York, I had the idea of watching Gravity in IMAX. I fell asleep twenty minutes in and woke up to an empty theater with the lights on. I still don't know what happens to them.

15. My first concert in New York was Paramore. A girl I met in line for a live taping of Jake & Amir's podcast had an extra ticket. I went, not knowing if it was a date and not knowing who Paramore was. I never saw either of them again.

16. If you are 19-years-old and Asian and live in New York and don't have a fake ID and want to watch the Patriots on Sundays but don’t have TV access, here’s a tip: find a bar that has other Asians and saddle up nearby them. Close enough that the bartender will assume you’re with them, but far enough that they won’t object. At some point the bartender might realize their err, but worry not. They won’t have the courage to ask.

17. My first manager at work started a week before me. Head of Marketing. On my first day I said, “did you know you’re more likely to die in a plane crash than click on a banner ad?”. I don’t know where I heard this but he declared it ”genius”. Later that day he showed me an app he used to battle rap against strangers. He lasted three weeks at the company. I was assigned a new manager on the other side of the office.

18. I ran three Twitter accounts during those first months in New York. My personal account, a Dave Portnoy fan account that was gaining momentum, and the official company Twitter account which my second boss let me run mostly unsupervised. All my tweets are still up. “5 years ago today OJ Simpson was sentenced to 33 years in prison. Also, [Company Name] joined Twitter. Happy anniversary to both of us I guess,” I sent, apparently, on December 5, 2013. My job required me to spend all day scrolling through "tech Twitter" trying to come up with a sentence or two to contribute. I learned how to tell who on the website was interesting and who was lame. This bootcamp paid off for me many times over in the years to follow.

19. Early on in the internship I wore my varsity wrestling windbreaker to work. In the elevator, a designer quipped that I was still wearing “high school gear”. I wanted to say I had just gotten this months ago, these were just my clothes. I didn’t wear it again.

20. My first time crying in New York, I was living in the Upper East Side. My bunkbed sublet had expired and I was now in dorm-style housing mostly occupied by international students. While watching 2004 Red Sox highlights on YouTube, I started sobbing. I called my mother, yelling, demanding to know why she hadn’t let me stay up to watch the games of the "the most historic comeback in all of sports". I was inexplicably hysterical. She was astoundingly patient. I guess she knew I just needed someone to talk to.

21. I wrote three journal entries during this first stint in New York. Here are excerpts from the first:

22. So im in nyc right now. 2 months into a 3 month stint. Working at [company name], which has been not as cool as i thought. Still a good experience, learning a lot. I would learn a lot anywhere though at this point in my career.

23. I remember sitting with [high school therapist] before I left for nyc and she told me that i would be extremely lonely living alone in the city and it was good i had side projects. I internally scoffed. Lonely? Do i look like a loser?

24. The first time i felt lonely was my first night in kolping [UES dorm housing]. Its like theres a hole in my chest, something gone. I skipped work today because im just exhausted. Ive had so much trouble getting out of bed this week. I think i might be a little depressed.

25. I havent talked to anybody today. Well, thats a lie. I ordered a small iced-coffee and a grilled chicken avocado panini at irving coffee roasters and then i got a starbucks refresher at starbucks. So 2 cashiers.

26. Out of self-preservation, I stopped watching my friends’ Snapchat Stories.

27. One weekend, I took a Megabus to visit my friend at Yale. In preparation of my first taste of college, I paid someone in the dorm housing to buy me a six-pack of Coors Light. I stuffed the contraband deep in my duffel bag. I suppose it was a gesture to show I was “with it”. When I later gifted the warm beers to my friend he just said, “Oh, okay, thanks. We have beers here, you know”.

28. I was offered an extension to my internship. The CEO liked my tweets. I declined.

29. I didn’t leave New York that December feeling I could make it anywhere. The saying doesn’t say: if you can’t make it in New York, what happens next? Where do you go? Philly, I guess.

30. I met up with "The Gates" friend throughout those months. We went to a Brooklyn Nets game and talked about Lorde's debut album. We ate dinner at a diner to celebrate the Red Sox World Series win. I saw the theater show he worked on. He took me to jazz. I dragged him to a Breaking Bad series finale event even though he didn't watch the show. We shuffled into a packed standing room only bar for the live viewing. People cheered like it was the Super Bowl.

31. I moved to New York two more times. The third time I stayed for six years. Until the very end, every time I toured potential apartments, deep down in a place I didn’t acknowledge, I asked myself if the space seemed cool enough for 2012 HBO characters to live in.

32. A few minutes after drafting the opening of this post, I called an Uber to pick me up from my Carroll Gardens sublet. It was one of those Ubers that is actually a yellow taxi and has screens in the back for trailers and games. The first video ad playing, as I buckled my seatbelt, announced a new augmented reality experience will allow you to relive the glory of The Gates. I got so excited by the coincidence that I took as many photos as I could. But maybe I shouldn't have been so surprised. Maybe I never learned this was just the kind of thing you should come to expect from this city.

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Thanks for reading. I promised myself when I started this Substack that I’d write five then take it from there based on the vibes. This is the third.