Jessa Gilbert

Jessa Gilbert

Update: 2025-11-03
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In this week’s episode, I’m joined by Squamish artist and backcountry guide, Jessa Gilbert.

Jessa’s approach to life seeps into her work, art and everyday- she has a knack for finding joy. Jessa has recently produced a short film “Drawn in” and done a live painting at the BANFF Film Festival and over the years has collaborated with brands such as Burton, Yeti, Leatherman and Roxy, as well as done graphics for the Women’s Adventure Film Tour and been in numerous mural festivals. Her works are brightening the towns and mountain slopes and bringing joy to so many places and spaces. As well as an artist, Jessa is a backcountry splitboard and hiking guide who froths the outdoors.

In this episode, we talk about her journey to becoming an artist and guide, her change in identity after injury, imposter syndrome and the power of having a team to make ideas come to life. “Seth Godin talks about imposter syndrome as this beautiful moment where you’re at the cusp of what you know and what you don’t. And it’s actually a really good place to be if you’re trying to do something new or different, because it means that you’re stepping outside of your comfort zone and into a new arena.”We also talk about the similarities in art and adventure in it’s ability to foster curiosity, bring joy and learn through trial and error. “It’s like, you gotta be good in your own head. You can be your best ally and your worst enemy on the same day, multiple times, but it doesn’t help you to beat yourself up.”

You can follow her epic journeys and works on socials, watch her film "Drawn In" and find out more about her on her website. Until next episode, Explore Your Core



This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit elisemarcianti.substack.com
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Jessa Gilbert

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Explore Your Core