Mar 7, 2025
What would you do if failure was a real possibility? If suffering was inevitable, but you had the option to walk away? Would you still go for it? My guest today, Kimberly Brookshire, knows this challenge well. She’s a long-distance hiker, a women’s adventure guide, and a passionate fly fisher—always choosing the hard path, the uncertain path, because that’s where she finds the most growth.
In this episode, Kimberly shares her journey from fashion and city life to hiking thousands of miles on some of the toughest trails in the U.S. and beyond. She opens up about why she keeps pushing her limits, how she finds meaning in suffering, and the lessons she’s learned from guiding women through their own adventurous pursuits. Whether you're an outdoor enthusiast or simply looking for inspiration to take a bold step in your own life, this conversation is packed with wisdom, humor, and a fresh perspective on what it means to live fully.
Episode Highlights:
[2:15] How a childhood filled
with adventure led Kimberly to long-distance hiking
[6:40] The pivotal decision to hike the Mountain-to-Sea Trail—and
why no one thought she’d finish
[15:20] Why guiding women’s adventure trips is about more than just
the outdoors
[25:00] Handling adversity on the trail: lessons from near
disaster
[37:45] The mental toughness strategies that keep Kimberly pushing
forward
[45:10] Finding the balance between solo adventures and guiding
others
[54:30] The Arizona Trail: what’s next on Kimberly’s adventure
list
Links & Resources:
- Follow Kimberly on Instagram: @kimberlybrookshire
- Learn more about the WHOA Travel for women-powered Adventures: WHOA Travel
- Check out the Mountain-to-Sea Trail: www.mountainstoseatrail.org
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