04/28/2014 04:02 pm ET Updated Dec 06, 2017

Chicago, I'm Breaking Up With You; Before You Break Me

I bought a ticket to the world
But now I've come back again
Why do I find it hard to write the next line?
Oh, I want the truth to be said
I know this much is true
-- Spandau Ballet

Dear Chicago,

I'm breaking up with you; before you break me...

It's mostly me, but it's you too. I've been deep inside you for the last seven and half years. It's been pleasant. It's been emotional. I fucking love you, man... always will. But the time has come for us to go our separate ways. My entire adulthood has been spent in this town and regardless of what any of your shitbirds think and despite my quasi-shitty-Madonna-ish-London accent, I consider myself a Chicagoan. This city has been hard and this city has been fair.


On July 20, my wife, two kids and I are leaving Chicago, America and the western world and moving to Majuro, in the Marshall Islands (I had to Google it too). I will be a History and English teacher of High School guys. I'm very excited/super pumped, bro, about this new challenge and very grateful for everything you've done for me. I'll miss you deeply (but not your winters or racism).

I met you in Humboldt Park on January 1, 2007 and, man, I've lived and loved in some of your supreme shitholes. My first half year in this town was fairly miserable. All I did was YMCA work outs in the morning and drink forties and smoke weed all afternoon. I had just moved from everything and everyone I knew, and despite fatalistic pride, it turned out to be some rough psychological shit. The boredom and purposelessness was often overwhelming and I was often a bit of dickhead to the one person who gave a shit about me (perhaps, a recurring theme?).

I got a job at an Alderman's office, which at the beginning was a refreshing challenge. I always dressed well; nice suits and shit. As a dedicated follower of fashion that was the trend at the time. Working for the city was the best way to jump headfirst into the belly of this brute of a town.

Politics is show business for ugly people and the ugly people are omnipresent, most of the time with awesome faux-Italian accents, insatiable appetites for booze and ill-fitting leather jackets. We do politics, often quantity over quality, more than any other city I can imagine. There's so many (read: way too many) elected positions. There's too much mediocrity, too much laziness and a plethora of other shit characteristics that people rightfully associate with government and the people who work in it.

A year after moving here I had a kid who, in reflection, has basically saved my life... it's almost a cliché for parents from working class stock to say having kids saved their life, but I'm a man who loves being cliché, despite staunchly protesting the contrary. This little motherfucker gave me everything I never knew I didn't have. Skip ahead seven years and she's my BFF. I love nothing (publishable) more than being hungover, eating ice cream and watching the WWE Network with her cuddling me on the couch.


Now, I live in a nice South Loop loft with the all-important exposed brick and the kid goes to a good school and blah blah... but despite these nice things, including two flat screen TVs, a hybrid car, yoga membership, a good job with a nice boss etc., I am not really happy anymore. I am complacent and that's fucking boring. I've always been one of those dicks who advocates constantly moving and doing new shit. Ingesting Prozac may have steered me away for a bit, but this move to Majuro is the next play.


I have come to develop an immense jealousy of people who grew up in lots of different places and have weird accents and no discernible sense of home and/or some dumb national loyalty. These are typically the kids of diplomats or really wealthy little trust-fund pricks, but that's what I want for my children. I grew up the opposite way and I want them to be much different and much better than me. Having them grow up all over the world is the best way I can think to achieve that. Also, a pack of cigs costs $2 in Majuro.

Chicago, you aren't perfect. You're beautifully flawed. There isn't anything wrong with you, that can't be repaired by the good in you. The most American-American city. The city that has given me essentially all I know and believe. I will miss you intolerably, but the time has come. I love you forever and, should we meet again, I'll be pretty tan and slim and able to climb a tree, bare-foot, really quick.

Yours in perpetuity,

Matthew Bailey. xoxoxoxoxo <3