On home: San Francisco vs. Chicago

My current, soon to be former, house was built in 1908, a few years after an earthquake leveled San Francisco. Big bay windows look out onto 18th street, a crazy stretch where you often see naked men strutting about — decorative puppet socks their only article of clothing.

Most mornings I walk down 18th to the corporate bus stop, stepping over heaps of broken glass from shattered car windows, squished dog turds and sometimes a few people, passed out on the sidewalk.

Then I stand at the bus stop and wait for the fleet of corporate shuttles, big white and WIFI enabled, to take me to work. And it seems so normal because in tech-SF this is normal. It takes leaving the Bay Area to realize that it is nothing but normal.

But my little walk is a microcosm of San Francisco, a city as dirty as it is beautiful, a city so incredibly wealthily yet on-the-surface poor. In some towns, gritty is gritty, here gritty is character. And it’s a city, whether you like it or not, that stirs some sort of reaction in everyone.

I’ve been here over a year and can’t help but to reflect and compare life here to life elsewhere.


Since 2007 I’ve never lived anywhere for more than a year. Seven moves in seven years. Often I wonder if I’ll ever be able to stay put. Every year as the end of my lease nears; the urge for a new place hits me.

And I think part of the reason I’ve always moved is that I hadn’t, up to this point, found a place that truly felt like a home.

Home is a feeling as much as a place.

Apartments in college were not homes, they’re places you live. People cycle in and cycle out. My high-rise studio in Chicago never felt like home. I never liked having a doorman track my coming and goings, or having to ride an elevator twenty-five stories with the 30-something single women who talked to their dogs like they were their boyfriends.

My current house, despite its quirks, feels more like home than anywhere else I’ve lived as an adult. And it’s a large part of why my past year and a half in SF has been so enjoyable. I feel comfortable here, relaxed.

And it’s unfortunate that, due to a owner move-in, I have to leave.

Not that my current house is perfect.

A few months back, I returned from dinner. I walked into the kitchen, flipped on the light switch and a giant rat scurried across the floor and under the stove. A rat, not a mouse.

“I can’t believe you pay $1500 a month to live in such a dump,” my mom had said when I told her the story. “If I were you, I would move right away.”

“To where?” I responded.

And in SF, that is not an easy question to answer.


Sometimes I under think big decisions and overthink smalls ones. Back in senior year of high school, I only applied to one college.

“What if you don’t get in?” My parents had asked.

I had a number of snarky responses. I really didn’t give the choice much thought. UIUC is a big state school. A school of that size is what you make of it. I would make it work. While my peers went on countless campus visits and agonized over their choices, I simply chilled.

When the idea to move to SF entered my mind last November, I acted on the impulse, pulled the strings and just five weeks later was living in SF, in a neighborhood I had never heard of before, living with a bunch of people I had never met.

A recipe for misery is to think about yourself a lot. The same applies to moving — if you don’t think much about it, you can’t really be stressed about it.

And sometimes I don’t understand myself, because I’m the type of person who will worry that I forgot to close the garage door. I’ll be biking to work, a quarter of the way there, and turn around to check if the door is closed. And it feels so silly to be at ease with major life shifts but stress about closing a stupid garage door.


Attachment to a city is strongly correlated to strength of relationships you have in that place. If you take a step back and examine Chicago (or even the University of Illinois) without any emotional attachment, they’re pretty bad.

Chicago is segregated, corrupt, violent, geographically bland and either too hot or too cold. But I’ll be the first to tell you that Chicago is an incredible place to live, especially if you grew up there.

If you examine San Francisco, you’d ask “who would be crazy enough to live in a city where the dumpiest of studios start at $2000 per month?” But again, I’d be the first to tell you that it’s worth every penny.

A relationship with a city has similarities to relationship with a person. A city soon becomes so much more than just a place; it becomes a mash up of memories and experiences.

And I love both Chicago and San Francisco, for very different reasons.

Chicago is a city for people who enjoy cities. It has world-class restaurants, sports teams and cultural institutions all wrapped up in a relatively high-density and affordable package. It’s big, often-overlooked, and catches people by surprise.

San Francisco is for people who think “being interesting” is more important than “being cool”. Because here, interesting is cool. And I often see people, like the purple haired woman singing while hula hooping in the park, who simultaneously care so little and so much about what people think of them. It’s a bit of a paradox when so many independent people can seem so conformist. Like I mentioned before, it is hard not to have a strong reaction to SF and personally, I love it.

I often find myself talking with people in SF and thinking “you did what?”. They’ll tell me about the time they lived on a boat for 5 years, their solo backpacking trip through Africa or how their obscure hobby is building replica mid-evil weaponry out of cardboard. There are a lot of strange people out here, in a very good way.

People in SF, or at least the people I interact with, are different from those in Chicago.


We can’t choose where we’re from but in an increasingly connected world it is much easier to choose where we live.

When you live somewhere, unless it completely sucks, it is hard not to become attached to it in some way. Because where you live says a lot about who you are. It’s why someone from Kansas City could say KC is the best city in the world and no one could convince him or her otherwise. Because for him or her, it probably is the best.

And that’s why; if you tell me that your city is the best city in the world I won’t argue back. It’s pointless.

Because if it feels like home, then it is the best city for you.

Home is a powerful force, just look at Lebron James’ return to Cleveland, but after a while the pull fades.

I moved to California with a two-year plan. “Chicago 2016”, I’d tell people. Now I’m not so sure what will happen. The longer I live in SF, the more attached I become.

The more it feels like home.

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