How taking it to the streets can change your life

By Caitlin Kelly

The young boys I just blogged about, Unlocking the Truth, are doing something odd and radical.

They’re taking it to the streets.

Down on the corner
Down on the corner (Photo credit: samgrover)

I did it too, at their age.

Clearly, this won’t work for many kids — their town or city is too dangerous, they lack the maturity to handle it or their talents are sufficiently-developed.

But the positive effect it had on me still resonates today.

I spent my childhood, ages eight to 16, between boarding school and summer camp, always sharing a room, always surrounded by other people. So I was used to being around a lot of people I didn’t know.

I was then making little bead necklaces, and took my box of beads and a needle everywhere with me, the way an Ipod or cellphone now accompanies and distracts many tweens.

I decided to sit on a ledge in Yorkville, Toronto’s intimate, safe, upscale shopping area, and try to sell my necklaces.

Where did the idea come from? Who knows. It never occurred to me that it might be dangerous or boring.

Pine trees growing in Toronto's Yorkville Park.
Pine trees growing in Toronto’s Yorkville Park. (Photo credit: Wikipedia)

And some people bought them. They stopped to talk to me. No one laughed or found it weird. It was amazing.

I went back, at 15, to sell hand-made envelopes, and at 19 to sell my black and white photos, mounted on matt-board, for $25 apiece. One of the city’s top fashion photographers of the time, who I knew, walked by — and bought one.

I needed no permits or license, just the chutzpah to put it out there, my personality and my talent. Lucky for me, both seemed to be appealing.

Then a woman stopped to look through my additional selection of color slides, and ordered one, printed into a huge poster, for her wall at home. It cost — in 1976 — $125, an enormous sum. I delivered it and she wrote me a check.

It bounced.

I was lying in bed at home, sore and bleeding from the surgical removal of all four wisdom teeth, when the bank called.

I knew a lawyer, even then, and sicc’ed him on her. I had my money within a week.

But it taught me a powerful and unforgettable lesson in when, where and how much to trust. Her elegant appearance and charming manner were seductive — and misleading. That’s a good lesson to learn at 19.

To her, I likely appeared a wide-eyed street kid who knew little and trusted much. Not for long!

SJSA Grade Six -  The Year I Rebelled
SJSA Grade Six – The Year I Rebelled (Photo credit: Michael 1952)

In my freelance work today, I’m using much of what I learned out there alone at 12:

— Think you have talent? Go test the market, face to face when possible

— Some people will be wildly enthusiastic

— Some people will cheat you

— Some people will be indifferent

— Some will sneer or dismiss your work

– Knowing young that you have specific, saleable skills or talents is empowering. You won’t starve!

— Being able to charm and engage your customers/clients/audience is huge

— Asking for attention, and managing it, can be stressful. Many kinds of work will require it

Here’s a video of Creedence Clearwater Revival singing “Down on the Corner”.

21 thoughts on “How taking it to the streets can change your life

  1. I remember doing the standard lemonade stand at a very young age, but also added my drawings of flowers which surprisingly people actually purchased. As I got a little older I started making some multi-colored yarn pom pom keychains which sold like hotcakes in the school yard. ha! I love the last photo. I just posted about my uniform days growing up in a Catholic school and revisiting all those feelings this past week when shopping for school uniforms for my children.

  2. All those things you mentioned you learned I learned as well. And being an artist, I have seen a few scams come my way. It takes a lot of guts to go out on a street corner and make money from your work. Yorkville was probably a good choice of venues.

  3. I think some of these are how I’ve gotten as far as I have today, though instead of selling my wares on a street corner, I sent out my work to reputable magazines and saw where I got responses. Perhaps I should try the street approach though, pass out flyers with info on where my books can be purchased. You never know where I might find a few buyers.

  4. If you have 10 minutes, this woman is brilliant and illustrates how making a living on the streets can change your perception…of how you interact with another human. And what it means to connect.

    I think she’s incredibly wise.

    1. Thank you!!

      This is perfect. What she’s talking about is subtle and difficult — trust. Trust that others will actually appreciate you (your talent) and support it. If and when they do, you have a sort of power that no “job” will ever replicate.

  5. Simon Fowler

    I’m going through a such struggle, but I reckon that the hardest part of our lives is to be enough impressive to grab someone’s attention. Mostly everything we do is based on our need to get attention, even finding someone to love is really a form of attention grabbing and so you can’t never give up.

    1. All true.

      But once you’ve done it — grabbed attention — you know that it’s possible. Then you can do it again with the confidence you did it once. It gets easier and easier over time. I’m convinced that self-confidence (not arrogance!) is one of the sexiest and most attractive qualities in a person at any age. They are “bien dans sa peau” — comfortable in their skin — and people flock to that.

  6. Your childhood experiences remind me of when I was a tween and would hustle for work in my neighborhood. After a snow storm, I’d go out with my dog and a shovel, and ask people to shovel their driveways for $25. Many times I’d have to convince them that I could do it. In the summer I would offer to do yard work. Interesting how the chutzpah of our youth can get diluted as we grow older (for some). I feel like I’m still learning the ‘art of asking’ and confidently grabbing attention, but am slowly and steadily getting better at it (again?). It helps to know what you’re asking for and why.

    1. I think we are so fearless when young(er) — and the world beats it out of us a bit, no? I feel, now, finally, again, the sort of self-confidence I had in my teens and 20s. I’ve missed it!

      1. YesYes, the world (life) does beat it out of us a little… but then hopefully we bounce back with thicker skin. I think an aspect of regaining the ‘mojo’ of youth is finding our professional legs, or feeling like we’re secure again on some level. Does that makes sense?

      2. Absolutely. The fearlessness of youth (mine anyway) was also a result of never having failed. I didn’t really hit a wall until I was 30, so it was a nice ride — and one hell of a shock when things went south.

        It’s only taken 20 years to get it back! 🙂

  7. Pingback: The Green-Eyed Monster: An Open Letter to People with Straight Hair | BraveSmartBold

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