Response Crafting

Chicago, San Francisco and New York: why we love one and don’t like the other two

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Chicago is happy and happy to be happy. Easy-going and easily eager (fair-weather fans and lovable losers, anyone??) and if you express any other emotions, Chicago fields it by fetching you beer. Or bacon. Or burgers. Or boats. Or sports.

Let’s be honest: Chicago is pretty much a golden retriever.

I liked Chicago. I was never crazy for it – never got gaga over it – but I could never bring myself to hate Chicago in the same way you can’t really hate a golden retriever. Even if you could, his simple-minded pleasantness would make him immune to it.

Don’t get me wrong, Chicago is smart enough. Hard-working, too, and plenty trainable. It’s just that at the end of the day, he’s no more complex than a roll in the park and a belly rub. (And what kind of person are you, really, if you don’t like those?)

People always say that the best part about Chicago is that it’s “right in between west coast and east coast – not just geographically, but politically, personality… pace.” They’re right. It is a little bit of everything.

But that also means it’s also not too much of any one thing. i.e., anything. 

You throw the ball and go on walks and all of this is fine and well… until one day you realize maybe you aren’t getting enough out of a city that stares at you, tongue out and tail wagging, for absolutely no reason. For four years straight.

And it occurs to you to go elsewhere.

(And it ain’t you, Chicago. It ain’t you. Don’t you worry your pretty little head – you were good to me. And before you know it, you’ll have brand new friends and have forgotten all about that one girl you once knew who, crazy enough, didn’t eat bacon.)

San Francisco:

San Francisco is definitely not a golden retriever. San Francisco may be available but never even pretends to know you, let alone try to be your friend.

What I like about San Francisco – what anybody likes about it (and it seems that it’s the tourists who are especially vocal) –  is what I see as its “intoxicating subtle roughness.” It’s like a hand-woven rug or the first sip of whiskey.

San Francisco is feminine; San Francisco is cool to the touch. San Francisco is, perhaps, a bit reptilian – beautiful without the easy answer of softness or gloss. And we like it.

It’s the creativity; it’s the promise of creation. It’s existing with one foot on the edges of subculture and the other immersed in true markets (finance, tech.) Nobody likes grit and grossness, per say, in and of itself. Rather, we like that grittiness is white space; a reprieve from the Play-Doh casting of other places.

And because it’s more than Play-Doh – or golden retrievers – San Francisco inspires much stronger feelings all around.

People who hate San Francisco:

If you Google “I hate Chicago” you get little more than a Bro Bible article wherein a Chicago native writes, in a self-deprecating but-still Chicago bro way, about the “worst” ways Chicago is annoying… like – get this – how Chicagoans actually eat at Grand Luxe Cafe and restaurant row and “try to fill emptiness by proclaiming FOOD as their passion.” (Ugh, I totally hear you. So annoying!) #goldenretriever.

Google “I hate San Francisco,” though, and you’ll get 600+ word rants on how truly deplorable this city is. A real cesspool of human depravity. The lowest of low. Worst of the worst. (It is, one person even threatened, “my least favorite big city”! Whoa, Pacha. Stand back. Anything but that!)

All the SF critics kinda cite the same reasons: dirtiness; poor transportation (public transit, parking, walking the hills.) They say that “people” (read: “girls”) are “flaky;” that people are “entitled elitists.” It’s too cold, it’s too expensive; not kid-friendly and nobody dresses up. It’s not only dirty, but also “filthy” (I found several people who cited both.) And on top of that, it’s full of lib’rals.

One person told me that what they hate about San Francisco is that “everyone has ideas.” Hearing this I was like “wuht? How are ideas a threat?” But others agree: tech bros “think they’re saving the world with their crackpot schemes aka ‘start-ups.'” Some people use the cop out: “it’s the hipsters.”

But if you take the opposites of that criticism, you can begin to shape an understanding of what the SF critics do like and look for in a city. You get things like: “Clean. Easy and reliable parking. Friendly, dependable people. Clean. Low cost of living. Republicans. Clean. Conventionality rather than new ideas or world change. Kid-friendly… Clean.”

Guys. That’s a suburb. You’ve pretty much gotchoself a golden retriever.

New York

I’ve never lived in New York and have only visited like two or three times. I liked it – though what do I know, being a tourist? But I liked it enough to feel I can say so. It’s got the economic (read: fissscal) diversity without any of that “social” shit: the idealistic or socialist or burning-man-istic bullshit. You either make money – in the ordinary ways – or you don’t. And you either work hard, or you don’t. End of story.

You don’t just work hard, play hard. You go hard. You get ready when you go out and you stay out until the early hours. Even dating is a competitive sport. Hell, even walking around is a competitive sport.

New York’s got the polish, but it’s also got a bit of the pretentiousness – and the impatience. They can be pretty and put-together when they like you, but they’re also not afraid to tell it like it is if you’re in their way.

Aren’t there sharks that eat their own siblings as embryos? That might be what New York is. Or maybe a swan – pretty, but then goes around killing people for seemingly no reason.

Don’t get me wrong – I like winning. And I like NY plenty. And maybe I could move there; I’d just have to prepare myself for zero-sum games first.

What it all means

I have heard that you either love San Francisco or you love New York. And when you love one, you hate the other.

And I started thinking about this in the context of Chicago, too – sweet kid brother Chicago (if New York is the hard-knocks older brother and San Francisco is the free-wheeling sister.)

And, more importantly, what it meant for personalities, because if cities are reflections of ourselves, then what sort of “self” does each city have?

Studies have been done on the personality spread of the United States, and they have found that there are three dominant types.

Americans living in the north-central Great Plains and the South tend to be “conventional and friendly;” those who reside in the Western and Eastern seaboards can be described as “relaxed and creative,” while New England and Mid-Atlantic dwellers are prone to being “temperamental and uninhibited.”


The study broke the states down by the big five personality traits: Openness, Conscientiousness, Extroversion, Agreeableness and Neuroticism.

The Midwest is more extroverted, more agreeable and less neurotic, but also more conscientious and less open. Both of the coasts are more introverted and less agreeable than the Midwest; less conscientious and with above average to high openness (west cost being the higher of the two.) Also, east coast is a lot more neurotic.

All of us as individuals fall somewhere on the spectrum of each of those. And it just might stand to reason that the cities we like – even love – mirror our preferences.

You can take a test to help you decide here. Doing so might explain why you hate the cities you do. It might even save you a move to a city you subsequently deem “too dirty.” Or, rather, one that seems more “idealistic” than “ideal.”


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