What Art on the Street Taught Me About Becoming an Artist

Five years ago I wandered through Art on the Street in downtown Guelph with a friend.

We were just coming out of lockdown. I had recently moved to Guelph and was coming off a mental health leave from teaching. I was already anxious about returning to work and, if I'm honest, I wasn't entirely sure what came next.

As we walked through the booths that day, I remember being completely captivated.

Not just by the artwork, but by the artists.

Here were people making beautiful things, sharing them with strangers, and somehow building a life around their creativity. I had been to art walks, studio tours, First Fridays, and festivals before, but this one felt different. For the first time, becoming an artist didn't seem like an abstract dream. It felt like something real.

That day changed the direction of my life more than I realized.

I met Preetam from the Guelph Arts Council and signed up for their newsletter. That led to their mentorship program. Later I worked at the Arts Council for a maternity leave and eventually coordinated two Art on the Street events with the Downtown Guelph Business Association.

Art on the Street June 2023

Art on the Street June 2024

Art on the Street June 2025

For almost two years I helped support artists in my community.
Somewhere along the way I realized something.

I didn't just want to help artists. I wanted to become one.

One of the reasons I chose this path is because I want to better support future artists.

As an art teacher, I always felt there was one piece of my education that was missing. I knew how to teach art. I knew about art history and different creative careers. I'd even worked in museums and galleries before becoming a teacher.

But no one had really taught me what it meant to build a life as an artist.

What does a typical day look like?
How do exhibitions happen?
How do grants work?
How do artists actually earn a living?

So when I committed to my own practice, I decided I wanted to try everything.
Over the last four years I've worked in galleries and arts organizations, applied for grants, organized exhibitions, shown work in cafés and restaurants, and slowly learned what it actually takes to build an art career.

This year, after a year and a half of preparing, I finally became one of the artists at Art on the Street.

Standing inside my own booth on June 20 felt surreal.

Five years earlier I had been walking through the festival imagining what it might be like to be on the other side of the table.

Now I was there. Meeting collectors. Talking about my work. Watching people connect with pieces that had once existed only in my tiny studio.

It was one of the best days I've had as an artist.

It was also one of the hardest things I've done.

In the weeks leading up to the event I had to locate more than fifty artworks, frame them, package them, create inventory, design a booth, learn how to display work outdoors, and somehow transport everything safely.
Then there were all the costs that visitors never see.

A tent. Display grids. Booth weights. A payment system. Packaging materials.
Booth fees.

And that's before even considering the cost of making and framing the artwork itself.

The only reason I was able to participate this year was because I received a grant that helped cover many of those startup expenses.

The more I learn about this profession, the more I realize how many financial barriers exist before anyone ever sees your work.

At the end of the day I had made just over $500 in sales.

So was Art on the Street a success? Absolutely!
Not because of the dollar amount.

When I first attended five years ago, I saw beautiful booths. 

Now I see everything behind them.
I see years of practice.

Rejected exhibition applications.

Grant proposals.

Hours spent framing artwork.

Vehicles packed before sunrise. 

Artists acting as accountants, marketers, photographers, designers, salespeople, and small business owners, all while continuing to make the work itself.

Making art is only one part of being an artist.

Building a sustainable creative career requires an entirely different set of skills, and many of those skills are things I was never taught in school.
That's exactly why this journey matters to me.

Every exhibition, every grant application, every rejection, every sale, and every event teaches me something new.

One day, when one of my students asks me what it's really like to become an artist, I want to have an honest answer.

Not just how to paint.
Not just how to draw.
But how to build a creative life.

Five years ago I left Art on the Street inspired by the artists I met there.

This year I left inspired by the fact that, for one day at least, I had become one of them.

Art on the Street, June 2026