So, You Want My Job: Arts Entrepreneur
Jesse Robertson of Keep it Colourful chats about the magic of building a business, the restorative power of art and why adults are so darn hard on themselves
Photo: Jesse Robertson
JESSE ROBERTSON OWNS and operates Keep it Colourful, an interactive painting event for groups of friends and colleagues. She followed her artsy impulses at H.B. Beal Secondary School and then studied art, cognitive psychology and linguistics at Western.
She started nearly four years ago with the help of her mom, Pam, who runs the office today. She works with artist, Sara Komarnick, and two or three assistants. She tends to work at all hours, but when she takes a break, she turns on CBC Radio, cracks open a local craft beer and sits at her easel with her cat, Boo, nearby.
“And I’m in love with a wonderful man, Don, who loves dinosaurs and camping. Without him, I’m not sure I’d see the light of day because I’m literally always working.”
When and how did you come up with the idea for Keep it Colourful?
When I was 12 years old, I was diagnosed with an aggressive form of autoimmune arthritis. Simple tasks like dressing myself, standing up and walking became excruciatingly painful and sometimes impossible. I was left fairly incapacitated at a young age and had a lot on my mind. At that time, there was an artist living in our attic and I remember being up in his studio, drawn to the colours and feeling like anything was possible. It felt like infinity.
I’ve been painting every day since my diagnosis at 12 and am extremely passionate about the physiological and psychological aspects of art. It has restorative properties, and I just love being part of people’s painting experiences—especially those who don’t think they can paint or consider themselves artists.
How did you get the business off the ground?
We ran our first classes in a single room at a friend’s business centre. We’d get a liquor licence, bring in wine and locally made snacks, and zone-in for a few hours of painting. It was a really magical time. There are a lot of people who attended my very first events who are still coming today. Keep It Colourful combines painting techniques with a lighthearted experience in an embracing atmosphere. What I want most of all is for people to get out of their heads, escape routine and engage with art and creativity.
How does it work and what does it cost?
We offer social painting classes aimed at giving people a fun experience with art that pulls them out of their heads, out of their comfort zone and out of their routine for the night. It’s good to mix things up, and painting is a great way to detach from the everyday. Participants are led step-by-step through painting techniques, while being encouraged to go rogue and explore their artistic intuition. Our events are suitable for beginners and people who don’t necessarily have painting experience. We offer paint nights, team-building events, private paint parties, pour painting and family painting experiences, and cost ranges from $25 to $55 [per person].
What’s the largest group you’ve ever led?
I once taught 100 people. We used a projector and had four assistants. It was a buzz of laughter, encouraging words and colour.
What are the most popular images groups choose to paint?
They are diverse. Everything from sloths to sunsets. I specialize in animals and landscapes.
How far will you travel to put on an event?
I typically travel up to two hours to do events.
Best part of your job? Worst part?
It’s important for me to encourage people to create a space without judgement, expectation or discouraging thoughts. This is both the best and worst part of my job because it is the most rewarding. But it can also be the most difficult to attain. We often put unnecessary pressure on ourselves when we are trying something new. Being hard on ourselves is a thing adults do very well.
While painting, it’s important to focus on our thoughts and soothe our inner critic. Maybe we set out to paint a realistic barn, but what actually comes out is a wonky barn. Instead of judging the barn as bad, step back and ask yourself: Does it remind you of anything? Are there fuzzy dream-like parts? Is there an interesting abstraction? What did you learn? Did you make a personal breakthrough? What would you do differently and why? What did you most enjoy? The idea is that the things we tell ourselves affect our energy and have the ability to either create positive momentum or stop us in our pursuits. 
Interview by Christopher Clark