New York vs. San Francisco

New York vs. San Francisco

I deliberately chose San Francisco over New York, and in so doing, I deliberately repudiated being true to who you are in your 20s. Instead of choosing a place that feeds my best and worst traits, I opted to pursue a version of myself that I am not even sure exists.

Unlike New York, San Francisco certainly sleeps. My favorite cafes all close by 3 or 4pm, and good luck finding something to do - there are few places to even eat after 9pm. Despite living in a central part of the city, when walking around at night, San Francisco doesn't feel too different from San Jose (which, many are surprised to discover, is a much bigger city than San Francisco).

But a friend, visiting from New York, put it best - "I come to New York for inspiration and distraction, and I come to San Francisco for single-minded dedication."

What most people do not understand about San Francisco is that it is not a city. At least, it was never meant to be a city. The Spanish, and later the Americans, saw its merits as a defense location. But if it were not for several gold rushes (some literal and some figurative), it may not have arisen beyond what it is meant to be: a hamlet by the sea.

Yet San Francisco chooses to punch above its weight class. Or perhaps we disavow it of playing any other game. Covid and the possibilities of remote work led many coastal elites (often tech workers) to often say the words San Francisco and New York in one breath. It might seem odd that they are two cities to be compared - but Covid was not the first time that these two cities were situated in opposition to one another. Since at least the early twentieth century thought leaders have been trying to fashion San Francisco into the "New York of the Pacific".

I believe that technically minded "techno-optimists" - a specific breed of intelligent people - can be very happy in San Francisco. But to be happy here, you need to tolerate a lot of things.

You need to tolerate the fact that your cultural life is by and large an act of production rather than that of consumption. There is a difference between strolling a couple blocks after work to see an Improv show in Manhattan and hosting a makeshift Improv night with your friends in your home in Noe Valley. You also need to tolerate the fact that the diversity of your circle and of the people that you meet at parties is going to be limited to a different order of magnitude. Lastly, you need to tolerate the fact that the beauty of nature and of God's green earth will have to be a substitute for the beauty of culture and civilization that you find in any other major city on earth.

This may sound like a curse to many people, but there exists a certain subset of the population for whom this is a blessing. San Francisco, for all of its abstracting away of anything that may seem the slightest bit inconvenient, is a place where you can single-mindedly focus. You might be working on the wrong thing, and you might be totally detached from reality, but you have enough intelligent people around you that are also single-mindedly focused on their crafts. One might argue that technological development requires this kind of environment. Who knows? You might go far enough that the wrong thing may indeed bear fruits of some sort.

I am fortunate enough to be able to make a choice between the two cities. I am genuinely very happy in New York. I have more friends there, I have a stronger network there, and I might even argue that my educational background and work experience are better suited for that city.

In San Francisco, by contrast, there are honestly many times in which I feel like a second-class citizen for not being a Software Engineer that graduated from Stanford or Cal. I am not sure whether I am the aforementioned technically minded "techno-optimist" that is most at home in this city. I was never the type to take apart machines and I was never particularly excited by the latest gadgets or software updates.

Yet, I chose to live in San Francisco, and I choose San Francisco again and again whenever I visit New York. I did so because I am someone who suffers from chronically flitting from interest to interest, with nothing really to show for the collective time I spend on each passion. I knew that if I returned to the East Coast and moved to New York, I would only indulge these traits and become even more of a generalist than I am today.

At my age today, I believe that this is one of the last chances that I have to try and rewire myself into becoming a different kind of person. I want to see what happens when I become someone who becomes single-mindedly dedicated to a subset of skills. I'd like to see whether I can be truly happy by being someone that I don't think that I am - and whether I can surprise myself in the process.


I've received a lot of feedback on this piece, so I would like to respond to it here...

(1) I would agree that the strong monopolies of Big Tech have turned SF and the Bay Area as a whole into a "city of employees." I would love to see statistics to back this up, but it certainly feels as if tech has become more "corporatized" recently.

(2) New York City's "hustle culture" seems to take a different form in SF. At least within my immediate circle, my NYC friends seem far more interested in doing "side hustles" than my SF friends do. By contrast, my SF friends seem far more interested in taking care and pride in their "day jobs" than my NYC friends do.

(3) A concentration of diverse talented people, the feeling of the world at your fingertips, a balance of consumption and production, and being at a cosmopolitan metropole - to compare this to... single-minded focus? might be worth qualifying whether the two can't coexist. It makes me wonder how possible it is to resist FOMO in New York. I think I'd have a hard time.