Three Homeless Nights in Chicago

You know how sometimes you look at someone and you think, “That could be me in ten years?” Well, let’s hope those things never become true because in a decade’s time I’ll be a homeless black man.

I should back up here because you might now be confused, thinking, “That Chirpy, he ain’t a black man is he, niggah?” But before this devolves into casual, unfunny racism, no, I’m not black, and I’m not homeless. In fact, I’m about as middle-class and white as you can be without having The Daily Telegraph delivered every day to your three-bedroom-and-a-garage home in Kent. There are systems in place to make sure I don’t become homeless — Mum, if you’re reading this, I’ll have casserole for dinner.

But while staying in a commune in Chicago – or “community” if you prefer – I saw a little something of what my life could have been like in a man called Ron Brown. He’d been living in the place for twenty-something years and now had his pre-teen kid with him after an unhappy split with his wife. I got talking to him at the breakfast table one day, mainly, I suppose, because it was clear to everyone I wasn’t “supposed” to be in a place like that. But when you couchsurf you end up in some strange places, some more comfortable than others, some more interesting than others. My Chicago commune was definitely in the latter category.

Ron told me that, although he was homeless, he wasn’t actually unemployed. He told me he was a writer and had written for prestigious film magazines and had had lunch with Roger Ebert. I’ll keep saying “he told me…” because I’m not sure how true any of it was, but he told me writers don’t get paid much and I’m inclined to believe him; the only payment I’m getting for these blog posts is in Internet kindness points which, in case you weren’t aware, don’t hold much value and supermarkets don’t accept them; I’ve tried. But I have a real job too, one that does pay for rice pudding and haircuts and those kinds of things.

Ron reminded me that, contrary to advice given on every third travel blog you read, following your dreams doesn’t always work out. Remember that next time you go to a lecture on 18th-century literature or British social realist cinema of the 1960s.

My room-mate in the commune, a guy about my age with lots of medication on his bookshelves hiding titles like “Why Jesus Will Walk Again” and “The Rapture: A How-To Guide”, was the opposite. He was all about doing “what you feel is right” and other one-line slogans from a GCSE citizenship class. He was all noble and was a counsellor and had spent a summer in Devon (that’s England for you foreign types) offering counsel to alcoholics on a farm-based recovery program. He was about as interesting as a person with a monotone voice can be, which I mean in a kind way, I think.

He didn’t have any useful advice for getting to sleep in a room with no air-conditioning that remained at least 25C all night though.

I spent three nights in that place. Okay, well, two really, because I spent the third night asleep on the floor of O’Hare airport waiting for my early-morning flight to Charlotte, NC.

Now here’s a bunch of Chicago photos because the wall of text is hurting your eyes:

Chicago Skyscrapers with River

View from Hancock Tower in Chicago

Chicago Boats in Water

Chicago Painter

Chicago Wall Fountain Face

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18 thoughts on “Three Homeless Nights in Chicago

    • I did a creative writing class called “writing for a living”. All the guest writers’ best advice was “get a day job”. They weren’t even subtle about it. Freelancing is tough.

    • If you have a rich relative, blackmail them into giving you everything in their will, then kill them. Then you’re free to travel and write as much as you want and have the perfect life!

    • Actually it was the owner/manager who had the profile on couchsurfing. Jane I think her name was. She just showed up in a list of hosts for Chicago and she had a video link and a lot of information in her profile about the place and I couldn’t resist!

      • Wow, that is super detailed – video link? No wonder you couldn’t resist – I wouldn’t have been able to either! (Especially after Ghassab’s cave, I try to look for the more ‘interesting’ couchsurfing experiences ^.^)

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