Listening to Chicago


By Troy Headrick

Before I go any further, I’d like to ask you to watch this five-minute video about an extraordinary woman named Chicago Crosby.

OK, where to begin?  There’s so much I want to say.  I suppose I’ll start not with Chicago but with me and us, those of us who’ve just watched her story.

I live in San Antonio, Texas, a large city not unlike New York.  Almost daily I see people pushing shopping carts that look a lot like the one Chicago regular uses.

This video reminds me how often I jump to conclusions based upon what seems to be clear evidence right in front of me.  For example, I see a woman collecting cans, bottles, and other throwaways and imagine that I know everything about her.  I imagine that she is probably ashamed of her situation.  I think that she is likely uneducated and inarticulate.  I feel certain that she would almost certainly do anything to get out of the predicament she’s in—that, in fact, she thinks of her life as a “predicament.”  Conversely, if I saw a handsome man dressed in a suit, wearing expensive sunshades, and driving an immaculately clean luxury automobile down the street, I would almost certainly say to myself, “That guy’s got it made.”

Of course, I know that some people who collect recyclables for a living are unhappy with their lot and are victims of a heartless capitalistic economic system that allows far too many to fall through the cracks.  Also, it goes without saying that a portion of rich folks really do live ideal lives, but nothing is necessarily true because we think it to be true, because the accumulated “facts” seem to lead to a certain conclusion.  All this raises at least a couple of questions:  Where does such certainty come from and why do we so easily fall victim to sloppy thinking?  (Of course I know the answers to both of these questions but that doesn’t diminish the importance of asking them from time to time.)

Few things in life are as simple as they appear to be.  We have to continually remind ourselves not to stick people into boxes because it looks like they might easily fit in such boxes.

Chicago’s story also makes me wonder why we don’t automatically associate the concept of entrepreneurship with people like her.  She developed her business model, gets up and out early, works hard, solves problems, networks, expands her customer base, and keeps abreast of political developments that affect her bottom line.  If she’s not the perfect example of an entrepreneur, then I don’t know who is.

I was amazed to hear her say that her current life as a “canner” has more “substance” than her former one did.  Perhaps her most powerful comment—an important reminder to us all—came right at the end of the video when talked about how nothing in life “is a certainty” and that true survivors are those who are able and willing to adapt.  (Plenty of truth there.)

I’m curious what you thought about Chicago and her story.  I look forward to reading your comments.

Troy Headrick’s personal blog can be found here.

23 thoughts on “Listening to Chicago

    1. Exactly. I even fall prey to having certain expectations based upon what I see happening in front of me. Chicago is cool because she came across as incredibly sophisticated and nuanced in her thinking about her situation. She even preferred her present state over her earlier (and less authentic) life, the one she had lived before she ended up having to take care of her mother. Of course, whether or not she was being truly candid about this was certainly up for discussion.

  1. Initial judgements take us down preconceived paths and kills open minded exploration. To learn and grow we need to be explorers. Good post and it led me to Troy’s personal blog, which I followed. Troy, will you be posting more there or here?

    1. Thanks for asking about my personal blog. I’m very busy here and I’m trying to restart my art career so I don’t have a lot of time to post on Thinker Boy. But I’ve promised myself that I will become active on my personal blog again. In fact, it’s one of my main goals for this year.

  2. Thank you for sharing this. What an interesting story. I think it is so fascinating how people receive and respond to extenuating circumstances or large changes or shifts in life. What allows some people to rise to the occasion and others to crumble? Never assume right?

  3. The fact that she can make a living, help the planet, and do s in such a heavily expensive city as Brooklyn? Amazing! I like, her spirit and her attitude, and I wish more people were as vibrant and creative in their outlooks.
    Sadly, most of the people I see here with carts have all their “worldly goods” in them. Where I live, near a major highway, the panhandlers are ruthless. Would I be ticked off if they were taking my recyclables out of the trash and making a living off of them? So long as they didn’t leave a mess, it’s no big deal. Recycling is recycling.
    THe biggest point that comes across is that if you want to find a way, you will. Maybe you’ll have to change your outlook, your expectations for the day, or change your long term goals. It sounds like it was totally worth it for Miss Chicago.

    1. I sometimes feel that things are hopeless until I see a person like Chicago. She reminded me that things are never so bad that there’s not some creative way out. I just wish I had half her spunk and optimism.

  4. Only in America, and other third world countries. She’s an articulate lady who could be a teacher but she can’t afford the tuition. So she’s doing what she can (pun intended), with good humour and attitude, which is admirable. Would she prefer to do something else, given the choice? You can’t have equality of choice without equal access to education and healthcare. Without capitalism-and-socialism together.

    1. Having lived in five countries over a period of about twenty years, I would certainly agree that America is a second-rate country (at best). (By the way, I hate the terms “first world” and “third world” for a lot of different reasons. My hope for America is that it can become a lot like many parts of Europe–I’m thinking the Scandinavian countries, in particular. Unfortunately, America seems to be taking a ugly, dark turn, but the vast majority of young Americans are extraordinarily progressive. It sounds like you and I have very similar political views. Thanks so much for reading and commenting.

    1. So true! If we could be courageous enough to live simple lives, more of us would feel happier and freer. We often confuse needs and wants. But our capitalistic word wants us to confuse these things. Powerful corporations spend billions of dollars to screw with our heads so that we conflate these two. Thanks for the fabulous comment.

  5. I admire Chicago and her perseverance. I want to be her friend. And I think you make an important point, Troy. How easy it is to judge! We never know what someone is going through. And, to your point, what may appear as drudgery, may in fact be someone’s hope. Thanks for posting this!

    1. Thanks for the comment. Watching this video was a reminder that I often jump to conclusions about people based upon their socioeconomic situation and so on. This is so unfair. But our culture teaches us to be so judgmental, to “read books by their covers.” We all need to remind ourselves that almost everything is more complicated and nuanced that it first appears to be.

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