Some Thoughts on What Makes New York so Great.

I have, surprisingly, become New York City's biggest apologist.

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For as long as I can remember, I’ve suffered from a chronic case of wanderlust. I romanticized travel to the point that I wanted to be on the move 24/7, and any time not spent somewhere new was spent planning the next trip to somewhere new. In late 2021, for example, when I was living in Atlanta, I bought an impromptu ticket to Barcelona that led to me spending four months vagabonding around Europe (for further reading, go here). Within two weeks of returning home for Christmas, I was itching to get on the road again, and I rented an Airbnb with a friend in Buenos Aires, Argentina for a couple of months, working remotely in the meat and wine capital of the world.

Even when I wasn’t breaking out my passport, I still wanted to be on the move domestically. The summer before that Europe trip, I visited friends in Pittsburgh, DC, Charleston, and New York over a six-week period, and a month before that, I took a road trip across the western US with my best friend from college. This longing for travel ran deeper than simple enjoyment (though, don’t get me wrong, I very much enjoyed it): it was a near-existential urge to see and do more, and more, and more. Sitting still drove me stir crazy; I felt like I was wasting my time.

In Fall 2022, that changed.

That August, I drove a U-Haul from Atlanta to Manhattan to kickstart my move to New York for business school. Business school is, by itself, a blast. And New York City is, by itself, a blast. The combination of the two was a dopamine tsunami.

I had new friends in a new city with a new restaurant/bar/club/pizza joint to try every night. Everyone looked good, dressed well, and walked 25% faster than residents of other cities. There was something to do every second of every day if I wanted to, and it was awesome.

But I was still feeling the residual pangs of wanderlust, so, after Thanksgiving 2022, I flew back to Latin America for a week to visit a friend (my roommate from the prior Argentina trip, actually) who was working remotely from Medellín, Colombia. For the first couple of days, we had a blast. We got to explore a new city, check out the best restaurants and bars in El Poblado, somewhat unsuccessfully attempt to hit on Avianca flight attendants in a nightclub called “Perro Negro,” take a sky tram across downtown, and climb the stairs to the top of the now-gentrified Comuna 13 neighborhood, Pablo Escobar’s former home. But by day five, I felt something unfamiliar: I was ready to go home before the trip ended. Unlike previous travel experiences, in which I felt like I was missing out on something when I wasn’t on the road, I now felt like I was missing out by being away from New York.

I ended up moving my flight up by a day to catch the US-Netherlands World Cup match with friends at a bar downtown (in which the US, as we’re prone to do in international football, lost).

Since then, whenever I’ve spent more than a few days away from New York, I’ve found myself longing to get back to the city as soon as possible. I mean, come on, how could you not romanticize this place?

Picture taken from my favorite Argentines’ apartment.

The thing about New York is that it’s tough to get it until you’ve lived here for a few months. I visited a few times before moving here, and while I always had a blast, it was exhausting. Everyone was in a hurry at all times, the subway was impossible to navigate, I had no idea where to go for dinner and drinks because there was an infinite number of viable options, and I probably spent most of my time at the “not-touristy” spots where everyone visiting the city ends up when they’re trying to avoid the touristy spots (have you ever heard of Mr. Purple?). Even in my first few months living here, I was overwhelmed. I marked more than a 100 bars and restaurants that I needed to try in Google Maps, I panic-researched where to go shopping to upgrade my Atlanta uniform of golf shirts, chinos, and sneakers, and I nearly died 12 times riding a Citibike around Manhattan.

But now that I’m more familiar with the city, I love New York.

Having spent 25 months in Manhattan, which, I guess, makes me a New York toddler (?), I wanted to share some thoughts on what exactly it is that makes New York City so damn enticing.

Proximity drives socialization.

A lot of folks look back on college fondly, calling it the “best years of their life.” I think one reason for this is that everyone was young in college, and being young is cool. You were hot, you had hair, your metabolism was impeccable, and “the rest of your life” felt like an adventure waiting to play out. What’s not to like? However, another aspect of college that I think people long for after graduation is living near one’s friends. In college, if you had an hour between classes, you could hit the dining hall with friends or stop by a buddy’s dorm to play FIFA. If you didn’t have plans on a Thursday night, you could walk to the fraternity house and rally a crew to go to the local watering hole. If you were having relationship problems, family struggles, or just suffering from boredom, your friends were only a five-minute walk away.

Post-graduation, making plans is tougher. Folks tend to go to work, hit the gym, run a few errands, and go home. Maybe you catch a friend or two for brunch on the weekend, but that’s about it. It’s much, much tougher to maintain consistent face time with friends when that face time requires a 30-minute drive both ways.

New York is America’s one exception, where free time spent with friends doesn’t end at 22.

With a city navigable by foot, subway, and Citibike, where many of your friends live and work walking distance from your apartment and your office, seeing your friends regularly isn’t some Herculean task. It’s the norm. Combine close proximity with most people’s hilariously tight living conditions (most of my friends in New York make substantially more money than my friends in other parts of the US, and yet they live in 1-bedroom apartments paying higher rent than the latter’s mortgages), and people want to get out and socialize.

A few recent examples of proximity at play:

• One of my best friends from business school works a block away from me in the Meatpacking District, so if we’re both having a slow Thursday afternoon, we can step out to grab coffee and hang.

• I host a ~weekly poker night on Wednesday nights, and it’s convenient for folks to grab dinner after work somewhere nearby before walking to my place.

• One of my best friends hosted an asado on his rooftop last Sunday, and I got there via 15-minute bike ride alongside the Hudson River.

• Pretty much every weekend involves at least one impromptu conversation in the group text that goes something like this: “Anyone out in XYZ part of town? Yes? Come hang at _____ bar.”

The benefits of living in America’s one city not defined by automobile ownership are nice. However, while American car culture is much maligned because it adds friction to one’s socialization, car culture is a sign of a wealthy, prosperous nation. Americans can afford suburban homes and two cars because we do a really good job of making money, which is great! But our prosperity has also led to our increased isolation. As the modern-day philosopher DJ Khaled would say, “We’re suffering from our own success.” New York, however, is an American anomaly because wealth isn’t synonymous with suburban isolationism; it’s correlated to urban proximity. All things being equal, you pay more to live closer to the action, not further from the city. The ease with which I can see the people I care about more than justifies the premium that I pay to live here.

Your environment is an adventure.

Looking back, I think one reason I romanticized travel to the extent that I did was because I was looking for something new in places where I wasn’t. I found the mundanity of my day-to-day life to be stifling, and I wanted a little adventure. A little novelty.

New York is nothing if not a novelty-rich environment. The city is teeming with opportunity and mystery, and at any given time, you’re one conversation away from a new friend, employer, or love interest. There is a near-infinite number of venues to explore, from restaurants and bars, to museums and art galleries, to tennis and basketball courts, to eccentric streets lined with vintage shops and Georgian/Turkish/Lebanese cuisines.

You can, in the same day, walk outside on a Saturday at 12:30 PM to grab brunch with friends in the West Village and stumble out of a Brooklyn club at 4:32 AM to take an Uber home, all without ever returning to your apartment. New York is the closest thing we have to a true open-world adventure where, if you’re open to it, you can discover something novel and intriguing every single day.

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New York cultivates ambition.

New York is egregiously expensive. My rent is $2,900 a month right now, which is, considering the neighborhood I live in, ironically a steal. My rent in Atlanta in 2021, on the other hand, was approximately $950, and that $950 gave me far more space and a deck with a grill. (I don’t have a deck now, but I do have a fire escape, which is chill).

A lot of people balk at New York prices, and I get it! That first rent payment was a tough pill to swallow, and don’t get me started on broker fees. (I do think that broker fees are the worst feature of New York and should absolutely be outlawed. A broker gets a 15% commission for unlocking the door to a building and answering three questions? Really? It’s just an insane grift.) However, New York’s high prices are a feature, not a flaw. On a macro level, the city is expensive because 1) a lot of people want to live here, and 2) they are willing to pay a lot of money to do so. It’s a supply and demand thing: Manhattan’s population density is 72,918 people per square mile. Prices are going to be high.

On a personal level, however, high prices also incentivize ambition. You can feel that energy as you watch pedestrians quickly stroll across New York’s sidewalks and streets: everyone is walking somewhere with a purpose. No one wants to tell themselves, “I couldn’t cut it in New York, and I need to move somewhere cheaper.” The consensus is “Screw that, just make more money.” I think, especially early in one’s career, it’s invaluable to immerse yourself in an ambitious environment that forces you to sink or swim, because 1) your skills will improve much quicker and 2) ambitious environments cultivate opportunity.

This ambition isn’t limited to the desire for financial gain, either. There is a diversity of thought and interest in New York that stems from the diversity of its residents: you have people from all parts of the country (and world), speaking all sorts of languages and working in every industry imaginable, and the interactions between those people spark fascinating conversations. When you spend enough time in an environment like this, you feel compelled to become someone interesting, if, for nothing else, to contribute to the dialogue.

Everyone in this city is attractive.

This point isn’t totally unrelated to the last one: while high prices push people to strive to earn more money, the mean attractiveness of New Yorkers is a standard deviation higher than the rest of the country, and this heightened attractiveness brings with it a competitive dynamic. When you live in a city of 10 million people, and that population skews attractive, 1) everyone has options, and 2) you must be on your A-game to stand out.

This phenomenon goes beyond “Oh, everyone in New York is naturally attractive.” New Yorkers are in better shape than folks in other parts of the country. Walk around Dallas, Texas and New York City and tell me which population has a lower obesity rate. It’s strikingly obvious.

People here also dress really, really well. That is partly because every clothing brand has a store here, but it’s also because you are surrounded people with excellent taste and style, and that taste is contagious. If the people around you dress well, you will want to dress well. And, going back to the whole proximity thing, it’s much easier to do so when the stores you need to go to are a few blocks away.

The city itself is beautiful.

There is an architectural plight in America where the default residential building form that defines most new construction is the cookie cutter “modern” apartment building. You know, those rectangular, 80-unit homogenous monstrosities with an espresso machine and pool table in the lobby, engineered wood floors and faux-marble counters in each unit, and identical floor layouts for their 1BR, 2BR, and 3BR apartments. A combination of zoning requirements and the desire to keep construction costs low has yielded a society whose default residential building style is the architectural equivalent of missionary. That’s fine, I guess. But where is the taste? The sense of expression? The art?

One reason that European city centers are so beautiful is that they’re old, and their architecture reflects centuries of evolving styles. New York is one of America’s few old cities, with “pre-war” being the most common adjective preceding many apartment listings on Zillow and Street Easy, and the age of the city combined with its spatial limitations has created a landscape that is as aesthetically pleasing as it is expensive. Looking south from West 10^th Street, you have brownstone townhomes in the West Village and cobblestone streets in Tribeca framed by a background of the World Trade Center and its surrounding skyscrapers in the Financial District. 60-story office buildings in midtown give way to one of America’s largest urban parks in the north, and the silhouettes of the Manhattan and Brooklyn Bridges loom over the coffee shops in Seaport and Dumbo. In a world that continues to sacrifice aesthetics for efficiency, New York has proven that these two forces don’t have to be diametrically opposed.

Not only do they not have to be opposed. They shouldn’t be opposed. Spending 30 minutes strolling through Soho, alone with your thoughts, is quite the catalyst for good ideas, and glancing out of your office window at 8:45 PM to see the World Trade Center towering over a vibrant downtown Manhattan makes a grueling workday a bit more bearable.

Serendipity is the status quo.

Something I’ve noticed since moving to New York is that everyone either 1) lives here or 2) visits somewhat frequently. The internet friend —> IRL friend pipeline is alive and well in America’s most populous city, a phenomenon that isn’t replicable anywhere else, and in the last two weeks alone I’ve grabbed coffee with three online acquaintances just because “we’re both in New York, we should link!” Sure, if you’re in media, tech, or politics, you can build industry-specific networks in Los Angeles, San Francisco, or DC, but New York is a melting pot for everyone doing everything. And it’s awesome.

Those network effects extend beyond intentional meetups cultivated by geographic proximity: they include a million accidental run-ins happening every day. For example, I was invited to a dinner near Columbia’s campus a few months after I moved to New York that led to me speaking at a wealth management summit in Florida last month, all because the woman organizing the conference happened to be sitting next to me that night. This wasn’t some outlier occurrence, either. Half of my “professional network” (and a similar percentage of my current friendships) stems from accidental, serendipitous run-ins like this. If you’re willing to put in a little effort to talk to strangers and say “yes” to invitations, you’ll be surprised by who you meet.

The limits of what I imagined my life could be have expanded dramatically.

This is the most important point. I grew up in a South Georgia town with ~20,000 residents, where the primary conversation topics were Georgia football, deer season, and how the liberal agenda is destroying America.

Where I grew up, if you were fairly smart, you went to a smaller local state school. If you were really smart, you went to the University of Georgia. If you were a genius, you went to Georgia Tech. If you were me, you went to Mercer University because you really wanted to play football at the Division One level, and you weren’t big enough or fast enough to play at Georgia or Georgia Tech. My idea of “life,” as a 19-year-old, was to graduate with a business degree, get a job in Atlanta, and work my way up one of many Southeastern corporate ladders.

To be clear, there’s nothing wrong with this path, but I wasn’t even aware of other paths. How could I have been? No one from Tifton, Georgia moves to New York. In fact, the idea of moving to New York was closer to “moving to Tokyo” than it was to moving to Atlanta. As a kid, my frame of reference for what I could accomplish with my life started and ended in the Southeastern United States.

Moving to New York was a red pill moment that showed me the range of possible outcomes was wider than I could have possibly imagined. My friends are journalists, investors, oncology researchers, bankers, comedians, traders, startup founders, engineers, consultants, and designers with dreams, goals, and ambitions that range from building billion-dollar companies, to curing cancer, to writing New York Times’ best-sellers. It has been invaluable to me, both personally and professionally, to live in an ecosystem that has exposed me to so much of, well, everything.

The direction of one’s life is dictated by 1) their experiences and 2) how they respond to those experiences. Living in an environment with such a breadth and depth of experiences has reshaped how I’ve thought through my own life. For someone whose existential fear has long-been a life defined by mundane routine, living in New York has provided an unrelenting spark of novelty, inspiration, and joy that I’ve never experienced anywhere else.

I mean, yeah, the rent is still expensive, but that’s a feature, not a flaw, of living here. And I’ll gladly take that trade every time.

- Jack

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Jack's Picks

• As of last week, I can add podcast host to my resume. Through my company, Sherwood News, I’m cohosting a markets/business podcast called “Snacks Mix.” Last week’s episode covered a potential Google breakup, Tik-Tok as the new nicotine, gambling in the Middle East, and a wild feature story on a mystery billionaire’s estate tax. Check out the new pod here.

• Emily Sundberg is one of my favorite new finds in the writing world (check out her newsletter, Feed Me), and she wrote an excellent piece concerning how the ease of online publishing (she pointed out Substack specifically, but it applies to much of the internet) has created an environment where folks are “monetizing diary entries.”

• One of my favorite anonymous finance meme pages, High Yield Harry (he does actually work in private credit, so the name fits), published a good piece for young professionals on avoiding office politics and managing salary negotiations.

• There’s an absurd lawsuit going on in Vancouver right now involving a carpenter-turned-day trader who turned $88,000 (Canadian dollars, so it’s not real money, but close enough) into $415 million trading Tesla options, before, as you probably guessed, blowing it all. He’s now suing the Royal Bank of Canada for, among other things, a complete disregard of fiduciary responsibility (the trader was an RBC Private Bank client). Anyway, I wrote about the story in a column last week.