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Jun 5, 2026 49 min

Why Being a Beginner Again Matters with Michelle Wilcox

from outside is Magic Hosted by Christopher San Agustin

Meesh and I have known each other a long time. Mutual friends, overlapping rides, the kind of friendship that started by crossing paths in the same places and got real once we both landed in Portland. We come at this work from the same spot too. Two people who spend most of the day alone behind a screen, then go looking for the exact opposite. A trail, a group ride, something printed you can actually hold. There's a tension we both keep circling. We love the outdoors, and we're also being pulled deeper into the digital tools that make our work possible. Knowing where to stand in the middle of that is harder than it sounds. We get into building community through bikes, the burnout that comes with organizing and learning to share the load, teaching yourself to code as a bike courier, the pull toward tangible things in a digital world, and why she's been chasing the feeling of being bad at something new. Michelle Wilcox is a web engineer who taught herself to code while working as a bike messenger in San Francisco. That path took her to Strava, and these days she builds the tools that help public transit agencies keep cities moving. Outside of work she's an organizer at heart, the person who builds the rides and races that pull a whole community together. outside Is Magic is a podcast about the intersection of creativity and the outdoors, hosted by Christopher San Agustin, founder of Broken and Coastal. Subscribe for new episodes. If this one hit, share it with a friend who needs a push to go be bad at something. #outsideIsMagic #CreativeLife #Cycling #CommunityBuilding #DesignPodcast outside is Magic is hosted by Christopher San Agustin. Produced by Broken and Coastal. Follow us on Instagram @brokenandcoastal Help spread the magic. Hit follow, drop a review, or share the episode with someone who gets it. You never know who it might inspire.

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Meesh and I have known each other a long time. Mutual friends, overlapping rides, the kind of friendship that started by crossing paths in the same places and got real once we both landed in Portland. We come at this work from the same spot too. Two people who spend most of the day alone behind a screen, then go looking for the exact opposite. A trail, a group ride, something printed you can actually hold. There's a tension we both keep circling. We love the outdoors, and we're also being pul...

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Why Being a Beginner Again Matters with Michelle Wilcox

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