Jessa

Q and A with Jessa Gilbert

Artist, Guide, Snowboarder, and all around Badass


BY:
Todd Heath

This story was first published in Issue #27, buy your copy: HERE.

You work at Baldface Lodge, right?

Yes! I’ll be there lots this winter — can’t break away from that place…way too fun!


How’s your mental health? Honestly though, we like to keep it real.

Right into it! Mental health is ALWAYS a work in progress. Rationally, I see everything is great; I have a roof over my head, food on the table, and I get to work in the most creative and playful ways I could have imagined. That being said, there’s the internal pressure I put on myself that I’m learning to balance. There have been days that feel overwhelming; lots of projects on the go, and a real moving target as I navigate creating a career in guiding and as an artist. I’m finding more comfort in sharing that the process is nuanced— I feel tremendous gratitude and excitement for the work I do, AND I feel, at times, incredible anxiety about how it will all come together. I’m sensitive, which allows me to do the work I do, and to connect with people… I love that side of me. The more we vocalize the true swings, highs and lows, the more we perhaps will all feel connected. We need to honor the down days, because they allow us to grow and to really see how expansive the good times are.


What books are you reading right now?
Do you have a favorite author?

A bit between books at the moment. I just finished Endurance by Alfred Lansing, which documents Shackleton’s wild voyage to Antarctica way back when. It’s a wild tale, and is giving me so much inspiration as I pack my bags to head to Antarctica this month! I blew through Dave Grohl’s book The Storyteller and Matthew McConaughey’s Greenlights. I love a good autobiography, and those two had so much insight to glean from them as well. Honest, humble, and vulnerable. Seth Rogen’s Yearbook was another autobio I loved laughing to. Listen to the audio version; it’s so good to hear his laugh while recounting stories.

The more we vocalize the true swings, highs and lows, the more we perhaps will all feel connected. We need to honor the down days, because they allow us to grow and to really see how expansive the good times are.


Jessa Gilbert
Jessa gilbert art

Did you always plan on being an artist? What inspired you to follow that passion?

I think I always dreamed of being an artist, but wasn’t really sure how that would manifest. I created from a young age as a way to communicate and, in many ways, disappear from my surroundings. I was a really shy kid and I grew up in a hectic, split household with three brothers. Whether it be painting, playing music, exploring the outdoors, or snowboarding, curiosity and play have been my main drivers. If I’m honest, I got to a point in my mid-twenties where I assumed I’d always work a desk job, and paint on the side… the catalyst for taking the leap and creating art full-time was receiving my first public art mural in Whistler, BC. I told myself I’d take one year, at least, to try making it full-time through my own artwork and guiding… That was years ago now, and I’m excited to share that it’s growing… and I’m growing with it. Not that you asked, but my biggest takeaway and lesson from this whole experience has been that we need to stop limiting ourselves. We need to get out of our own way.



If I’m honest, I got to a point in my mid-twenties where I assumed I’d always work a desk job, and paint on the side… the catalyst for taking the leap and creating art full-time was receiving my first public art mural in Whistler, BC.


Jessa Gilbert
Whiteout Cruiser Jessa Gilbert

"Whiteout Cruiser" -Jessa Gilbert

Do you keep a daily journal?
Is it mainly drawings, or writing as well?

I have both. I have a journal dedicated to writing that I try to keep at every day, I have sketchbooks from decades ago that are full of just drawings, and I have books that blend the two. I think it’s important to get things out of your head: positive, negative, nuance, etc. Freewriting has been a therapeutic practice of mine for a long time. I don’t know where the journals will end up permanently, but I do gain so much by going through them at times. I think process is important, and these journals are, for me, physical reminders of that growth. Some days, when I feel like I’m not doing enough, I look at my bookshelf and I can see the editions of journals and sketchbooks from over the years. That alone, without even opening the covers, gives me some peace of mind that, while I may not have the definitive answers to everything, I’m doing the work.


What challenges have you faced as a female artist
and as a snowboarder and guide in a predominantly male sport?

I’ve received remarks that are inappropriate or sexist in the art and outdoor arenas, absolutely. I’ve overheard guests scoff at having “the girl guide,” and I’ve been told directly that I “come off as too girly” by an instructor (a female, at that). I try not to think about those things too much, because they’re limited. More challenging for me is the internal challenge that comes from working within these male-dominated spaces. I have so many great mentors in my life, male and female, and I’ve found more open arms than closed doors. I’ve been a stubborn girl since inception then grew up with three brothers and felt the need to constantly prove myself to be an equal to the boys. That’s stuck with me, for better or for worse. Before anyone tells me anything, I have the mindset of needing to prove I’m good enough, not just for a girl, but for any measure. I’ve felt imposter syndrome, self-conscious about my decision-making, and have second guessed if I’m doing the right things. I’ve looked around the table and wondered “How did I get here? When’s the ball going to drop?” I’m working to grow beyond that inner dialogue. To paraphrase Dave Grohl in his book Storyteller, “sometimes you need to stop looking around the table wondering how you got there, and just enjoy the party.”



Before anyone tells me anything, I have the mindset of needing to prove I’m good enough, not just for a girl, but for any measure. I’ve felt imposter syndrome, self-conscious about my decision-making, and have second guessed if I’m doing the right things.


Jessa Gilbert
Goodnight moon

"Goodnight Moon" -Jessa Gilbert

Who has been your biggest
influence in snowboarding and art?

In art, I gravitated towards the classic painters like Van Gogh, Matisse, Helen Frankenthaler and Cezanne — their use of color to evoke a feeling I find so beautiful. Julie Mehretu and Kehinde Wiley I love for their patterning and twist on portraiture. Nick Cave’s Soundsuits are beautiful. It’s a bit of a mixed bag. For snowboarding, I grew up seeing Kelly Clark as this superhero of a woman boosting out of the pipe, and Jess Kimura was setting the standard for women’s street riding… major influences for me. I had a huge girl crush on Spencer O’Brien after she was my coach at Camp of Champions way back in the day… I might regret saying that out loud here, but whatever, haha. Craig Kelly has become a bigger influence now than he was for me growing up - I didn’t really look at big mountain riding as a girl in New York State, but as I learn more about his legacy and the life he lived, stepping into the backcountry from a freestyle background, the impact is real. Nicholas Mueller makes snowboarding look so fun, Robin Van Gyn and Hana Beaman are a joy to watch and spend time with in the mountains, Austen Sweetin has some crazy, wild energy, Travis Rice is a beast in the mountains, and the list goes on and on. Snowboarding has an amazing culture of people.


For snowboarding, I grew up seeing Kelly Clark as this superhero of a woman boosting out of the pipe, and Jess Kimura was setting the standard for women’s street riding… major influences for me.


jessa gilbert
Bomb snow jessa gilbertt

"Throwing Shade" - Jessa's art on the cover of Issue #27

What recent project have
you been most excited about?

Working on Fabric was a real treat—I’m so inspired by all the women that worked on and were featured in that documentary piece. Hats off to Robin Van Gyn for bringing us all together, and sharing her vision with the world. I finally got around to creating my own products, a small limited collection, but it’s made nonetheless. All locally sourced and locally printed in Squamish— stoked to finally check that off!


Tell us more about the documentary series, Fabric, that you were a part of.

Well, everyone should watch it. It’s a six-part series free on Red Bull TV that showcases the lives and stories of women who are using snowboarding, skating, surfing, art, and culture to make a difference in their communities. I was featured in Episode 2, Adaptation, alongside Maria Thomsen, Sanoa Olin, and Hanna Scott. I almost don’t want to go into too much detail, other than the fact that EVERY person shown is a beautiful story and a powerful force. •



Some days, when I feel like I’m not doing enough, I look at my bookshelf and I can see the editions of journals and sketchbooks from over the years. That alone, without even opening the covers, gives me some peace of mind that, while I may not have the definitive answers to everything, I’m doing the work.


Jessa Gilbert
Jessa Gilbert 594 A3 F0 F 057 B 4108 AD2 B B8 CEA6 FFB1 AC


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