Kailey Sheppard

Creating Art and Self-Compassion: Kale Sheppard’s Lifelong Path to Professional Artistry

“I've actually been doing art my whole life like ever since I was very, very little. That's something I always wanted to do,” Kale Sheppard explains. They live and create art in Winnipeg, Manitoba, where they got their big break. Their home community is Postville, Labrador and they grew up in a small town in southern Manitoba. Now a full time visual artist, Sheppard works in murals and digital illustration, and is looking to do more bone and stone carving.  

“I was given an opportunity by the Winnipeg Art Gallery to create my first mural then it became another mural and from there I guess murals really jump-started my career. I worked in murals and then I got jobs in digital illustration. I've had more and more opportunities pop up as I've advanced in my career and it's been really awesome,” they smile. They’ve also been learning about carving from a local artist who connected with them through the gallery. 

They credit the vocational school they attended with their initial growth as an artist, a place which gave them the chance to work with many different materials, solidifying Sheppard’s desire to have a multi-disciplinary art practice. They took any available arts course, from jewelry arts, hairstyling, to drama in school and as many free programs after school as possible. From printing to collage, through free workshops and researching online, Sheppard deepened their practice at a time when tuition and going to school just wasn’t in the budget. 

Growing up in a lower middle-class home, Sheppard knows financial struggle.  “I've had times living paycheck to paycheck and can't always meet my bills so I don't have the funds for art supplies necessarily, or things like that. But when I have been in those situations, I never let it stop me,” they relay. Sheppard has relied on programs that provide free art supplies in the city, or purchasing through thrift stores and dollar stores to keep creating. 

“I've always found ways to work around it so that I never have to stop doing what I love.”

Sheppard was also bullied in childhood, their family moved often and Sheppard also struggled with their mental health, making completing commissions and meeting deadlines difficult. Good support systems and self-compassion have been crucial.  Over time, they’ve found the lack of structure in artist life can be a blessing and challenge. 

“It's not like a typical nine to five job, there's no set milestones for telling you that you're doing things correctly. It's free flowing, and you make your own schedules, routines and standards for yourself. It's very easy to get caught up in your head with that,” Sheppard offers. 

If they could give advice to their younger self it would be to take advantage of more opportunities. “For as many classes and things as I did do, there's probably 10 other ones that I didn't do that would have really been helpful,” they remember. They could have received a jewelry metalsmithing degree through the free courses offered by their vocational school and they regret not doing so. 

Illustration by Shaikara David

In contrast, as an emerging artist, they took every job they could and found they were getting burnt out. “Now I feel stable enough and confident enough to turn down the job opportunities that are smaller,”they report, recounting how they’ve reduced their workload by knowing and respecting their limits.  

“I have done enough pushing myself to my limits and I need to be kinder to myself.” 

Now they take breaks and ask for extensions, not sacrificing their mental health to meet a deadline and trying not to be hard on themselves for doing so, knowing people who want to work with them will understand it’s worth the wait. They schedule time for themselves with extended breaks to relax and reset. 

That rest is important because the pressure to constantly post and make new things for the internet is exhausting. “That's not how the creative flow works. Getting out of that and making art for myself rather than for other people has been a huge help to my mental health, just finding that balance that works for me, because it'll be different for everybody,” Sheppard confides. 

When short of inspiration, Sheppard looks outside. “I've always found inspiration in nature. Nature's probably my first artistic love. I spend a lot of time outdoors and the natural design of everything is so beautiful,” they share. The perfect art of nature sparks Sheppard’s own imagined creatures, monsters and world building.

Creating art has also been therapeutic. “That was a big part of my adolescence, just drawing what I feel rather than keeping it bottled up inside. Even if it was just sitting and scribbling on a page until I felt better,” Sheppard recalls. 

“More recently, I've been using it to reconnect with my Inuit culture because I didn't grow up in my community. I grew up in Southern Manitoba where nobody had even heard of Inuit. When I moved to the city, I still didn't hear about it. I wanted to learn more about where I came from. I found out that art is such a huge part of Inuit culture,” Sheppard smiles, explaining how reconnection to culture has shaped their ever-evolving style.

Their advice to youth and aspiring artists is to practice, saying, “The more you do it, the better you're going to get.” Even for themselves, when they aren’t practicing or pushing themselves, their art doesn’t improve. They’ve also learned how helpful references can be, iterating from photos without stealing someone else’s work. “It's a great exercise and will definitely help with your skill building,” they affirm. 

After illustrating so many Fireside Chats for Instagram, Kale Sheppard is excited to be in one personally. Making art is something they’ve always wanted to do, and something they’ve done their whole life ever since they were very, very little. After all that time and practice, the little artist Kale Sheppard once was has grown into a big talent.

Thanks to Alison Tedford Seaweed for authoring this article.

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Key Parts

  • Career
  • Identity
  • Province/Territory
  • Date
    March 29, 2023
  • Post Secondary Institutions
    No PSI found.
  • Discussion Guide
    create to learn discuss

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