How Squamish Artist and Snowboard Guide Jessa Gilbert Finds Purpose Through Creativity, Adventure, and the Mountains

Meet Jessa, the self-proclaimed CEO of “Jessa Gilbert.” While some people define themselves by their job title, with a title like CEO who wouldn’t? Others define themselves by what they create, how they move through the world, and the impact they hope to leave behind. Jessa belongs firmly in the latter category.

Based in Squamish, British Columbia, Jessa is both a visual artist and professional snowboard guide, two roles that might seem different on paper but are deeply intertwined in her life. Whether she’s painting a mural, guiding clients through backcountry terrain, or quietly observing how light shifts across an alpine ridgeline, her work is rooted in a simple idea: joy, play, and beauty are not luxuries. They’re essential ways we connect to the world around us.

Jessa grew up in New York State and studied art (and snowboarding, if you can believe that) at the University of Vermont before moving to Canada in 2013. The wilderness she found there changed everything. The landscapes, access to mountains, and sense of possibility convinced her she’d never leave. Through both art and guiding, she now aims to share that same awe and wonder with others.

Purpose Over Passion

Jessa doesn’t like to define herself solely by what she does. For her, identity is less about a job description and more about intention. She often talks about the difference between passion and purpose: passion is what excites you, but purpose is what guides you.

Her purpose is rooted in the belief that joy and play have real function in our lives. In a world focused on productivity and measurable gains, she sees value in slowing down, giggling down a mountain, or sitting still long enough to watch clouds drift across the skyline. These moments aren’t trivial—they’re grounding. They remind us that not everything needs to be efficient or monetized to really matter.

That philosophy shows up in her art. Her linework is light, curious, and playful, shaped by a desire to capture movement and fleeting moments in static frames. She’s fascinated by the challenge of expressing ever-changing environments—like shifting alpine light or the passage of time—in something as still as a painting.

For Jessa, creating outdoors started as a way to force herself to pause. To sit. To notice. To be present long enough to realize that a moment isn’t just a snapshot—it’s the entire day unfolding around you.

“It’s good to go and be a kid or childlike in the world because it puts you in the present moment.”

Art and Adventure as the Same Language

At first glance, the worlds of art and backcountry guiding might seem like opposites. One is introspective and solitary; the other is structured, high-stakes, and often type-A. But Jessa sees them as different expressions of the same skill: creative problem solving.

In the mountains, she’s reading terrain, searching for safe lines, and responding to changing weather. In the studio, she’s responding to emotion, light, and memory. Both require curiosity, adaptability, and a willingness to interpret what’s unfolding.

That crossover has shaped the way she guides. She isn’t just responsible for managing snowpack and safety, though that responsibility is immense. She also sees herself as a steward of place, someone who helps people notice the mountains beyond the single perfect photo or powder turn.

She likes giving people the lens through which to see.

Many guests get caught up in the moment on their phones or fiddling with bindings and end up missing something important. Sometimes all it takes is for someone to say, “Look over here,” for someone to notice something beautiful. The conversation, the weather, the feeling of sun on your face, the history of a valley—those are all part of the experience. If you’re only chasing the photo, she believes, you miss most of what the day actually offers.

Guiding With Intention

After nearly a decade in the guiding world, Jessa still asks herself each year why she continues. The answers are layered.

Part of it is the discipline of learning. Guiding demands constant recertification, updated safety knowledge, and a lifelong commitment to improving. That external structure fuels her growth in a way self-driven learning sometimes can’t.

“I like being a lifelong learner, and it helps to have direction that isn’t just me pushing the rock uphill alone.”

Another part is representation. The guiding industry is still heavily male-dominated, and Jessa is often one of very few women in the professional guiding space. She stays, in part, because she wants younger women to see that they belong there too. Taking up space, even when it’s exhausting, becomes a form of advocacy.

But the biggest reason is simple: it’s fun to help other people experience their best day ever.

She’s guided clients in places as remote as Svalbard and Antarctica, and while she loves riding powder herself, she often finds more fulfillment watching someone else have a breakthrough moment in the mountains. Seeing their awe, their excitement, their shift in perspective—that shared joy is what keeps her coming back.

Slowing Down to See More

There’s an irony in Jessa’s life.

Snowboarding and guiding often revolve around movement, efficiency, and reaching objectives. Her art asks for the opposite: stillness, patience, and presence.

Rather than viewing those impulses as conflicting, she sees them as balance. The mountains remind her to play and move. Art reminds her to stop and observe. Together they create a fuller relationship with the landscapes she loves.

Ultimately, Jessa’s work—whether it hangs on a wall or unfolds on a snowy ridge—is about helping people reconnect with the world around them. To see more, feel more, and maybe rediscover a bit of childlike wonder along the way.

Because in her view, the goal isn’t just to move through beautiful places as quickly as possible.

It’s to be present enough to notice why they matter in the first place.

And that’s the fine art of playing outside.

FIND OUT MORE ABOUT JESSA HERE