Leaving Chicago

Ten years ago, I was traveling around Argentina, working online as a freelancer. I had a great time traveling and thought I might live like a nomad for a year or two, but after a few months away I really missed doing comedy and on a whim I found a summer sublet in an apartment on Webster in Lincoln Park.

My plan was to stay for the summer, take some improv and sketch classes, and then move on to another city. I ended up staying for 10 years.

I stayed to join a community and write and put up shows and get on stage as much as possible and learn how to be a better comedian.

I think I succeeded. I’ve read the sketches I wrote in my first summer here, in the Second City writing intensive. They’re really bad. The things I write now, I think they’re pretty decent. They’re much much better than what I was writing ten years ago, and much better than what I was writing three or four years ago.

Comedy on stage didn’t work out for me the way that I hoped. That was heartbreaking. So I pivoted, before that as a word I knew. I started writing a lot and then making movies and found that I loved writing just as much, albeit in different ways.

I miss the stage sometimes. It’s a different feeling when a show goes well, a feeling that I haven’t found anywhere else. I could say that it’s like a drug, but I’ve done the drugs and they’re different.

I’ve been lucky to find great communities here in Chicago, first in comedy and then in film. Artists in Chicago are incredibly supportive and welcoming and eager to help each other out. People come from all over the country to study and learn here, to form groups and put up shows and write and rehearse and experiment and take classes and study.

I think that sometimes we take this for granted in Chicago, that there are so many people who come to a place and work really hard and devote themselves to a practice or a field or an art form. Of course there are other cities where this happens, but not very many, apart from New York and Los Angeles.

The beauty of starting in Chicago is that there’s not much industry presence and that means that it’s easy to be around people who care about the work more than anything else. The downside is that ambition means that eventually many or most of the people will move on.

I used to complain that the film community here was spread out and hard to find. That’s true to a certain extent, but after living here for a few years I’ve realized that that’s an unfair criticism. I think that in relation to the improv/theater community, it never felt quite as good.

That’s because improv always had natural meeting points — you were always going to a show to perform or see a friend and so you were always running into people. Film screenings are less frequent and production isn’t very frequent either. I only made about 1.5 things per year when I was directing video/film stuff in Chicago.

But after spending a few years in the film community, I found some really really great friends and I found myself in a place where I would often run into people when I went to a local festival or film event or just to see a movie at The Music Box. There were plenty of people to talk shop with, it just took some work to get there.

In my opinion, the best thing about Chicago in terms of artist development is the culture of showing up and working hard. I believe that this comes in part from the Midwest culture, an extremely hard-to-describe-but-ever-present culture.

In Chicago, people show up. They commit (and often over-commit) and keep their word. They work hard and don’t complain. They’re not superficial and they don’t create interpersonal conflict for the sake of drama.

When you say “let’s do a show,” people say “yeah, let’s do it. do you want to meet on Saturday to start writing? In the mean time, I’ll look at some possible theater options.”

I think it’s very easy to underrate this culture, but having lived in other cities and having talked to filmmakers and comedians in various cities around the world, I think that this kind of culture is not the norm, and that maybe 30-40% of success is determined by how people respond when you say “I’m going to do a thing.” It’s not every city where people encourage you and want to help out or join in or say “that sounds crazy but fuck it you should try it.”

Of course these are generalizations, but they tend to be true in my experience.

Anyway. I’m leaving.

It’s really hard to leave right now because right now it’s summer and Chicago is the best place to live in the summer — it’s magical in a way that only a city that experiences long dark freezing winters can be.

And it’s hard because I have great friends here. And practically speaking, it’s the easiest place for me to make a movie right now.

So why leave?

While I do have great friends here, a lot of my friends have left, and this isn’t an uncommon experience. For the artist community, a lot of people view Chicago as a stop along the way to somewhere else, with that somewhere being Los Angeles or New York. But I’ve also had a lot of friends and acquaintances, people who aren’t actors or comedians of filmmakers, move as well.

Most of my remaining close friends either have general plans to leave at some point in the next two years or a general sense that they would like to try living somewhere else.

It’s hard to form close bonds when all your friends keep leaving!

Living in Chicago has become easy for me. My days and weeks have become routine and I no longer have the feeling of excitement that I had when I first moved here. I don’t feel like there are any surprises waiting for me here.

I don’t want to be complacent. I want to experience a new culture and to see how things are in a new place. And yes, I want to pursue bigger opportunities. And travel, like really travel for a few months, without the overhead of rent and a gym membership and the burn rate that comes with being fixed somewhere.

This kind of major life change has always been exciting to me because they force me to evaluate everything I own and to question all the major premises of my life. Where should I live? How should I make a living? What kind of films should I make, and should I be making films at all? What is important to me? Why is Spain? Oú sont les Neigedens d’antan!?

So with a hunger for something new, something that I don’t yet know, I’m selling off most of my stuff, putting my books and a few important items into storage and leaving.

I don’t know where I’m going to land yet.

I’m going to travel for a bit and try living in some new cities before picking one to settle in.

These are my favorite things in Chicago:

The Music Box Theatre, on a Friday night when the house is packed and the organist is playing.

Seeing something fucked up and hilarious at The Annoyance.

The tacos.

The coffee.

The architecture.

Summer days with adventures that go on forever.

The lake shore, which I never spent enough time at.

The creative communities and creative people.

The painfully short autumn.

That every neighborhood is like its own little town with its own character and sense of place and culture.

The next-level restaurants that are actually affordable for non-wealthy people.

That I’ve never met anyone here who was trying to ‘become an influencer.’

The amazingly generous teachers I’ve had.

The fact that it’s so cheap to live here compared to other world-class cities. You can still come here and get a cheap apartment near public transit and afford to work on your thing.

And yes, I love the -50 degree days that come every few years in February.

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