The epic journey that took this WeWork community manager to new territory

Kelly Thompson reconfigured her life’s path by hiking the entire West Coast one step at a time

Superpower on the Side is a series that features WeWork team members and how they spend their time when they’re not at work.

For most people, getting from New York City to Seattle is a matter of a six-hour flight. For Kelly Thompson, it was a matter of a 2,650-mile, five-and-a-half-month hike—not to mention a seismic shift in mindset. The 37-year-old started her position as a community manager at WeWork Lincoln Square in Bellevue, Washington, in January 2019, but first, she had a goal to complete: a solo hike of the Pacific Crest Trail.

In 2018, the fitness enthusiast, originally from South Dakota, was a studio manager at an indoor cycling studio in New York City. She had a comfortable life, but was unable to shake the feeling that something was missing. “I was feeling a little stagnant,” she remembers. After an inspiring hiking trip in Mexico City, she spent a restless night researching hikes across the U.S. During a vent session, a work friend suggested she quit her job and hike the Pacific Crest Trail. The idea—to walk the route along the coasts of California, Oregon, and Washington (popularized in part thanks to its appearance in the Reese Witherspoon drama Wild)—sparked something in Thompson. Before she had a chance to change her mind, she walked in her boss’s office and gave notice. “I was a little sleep-deprived,” she says with a laugh. “So I wasn’t thinking very clearly, but I was like, ‘If I think too much about it, I may not do it.’”

After the commitment came the planning. As a hiker with relatively little experience, she had a daunting task ahead of her, and some friends and family worried that she was getting in over her head. “Some people were confused, because I wasn’t running away from anything,” she says. “I wasn’t going on this big spiritual journey. I just knew there was something else I wanted to do in life, and I wasn’t sure what it was. I figured if I took a break and did something big outdoors, it would give me a little clarity.”

On April 27, 2018, she set off on mile one, heading north from the California–Mexico border toward the Washington–Canada border.  The journey was not without its challenges—sometimes punishing ones. She traveled through northern California just as devastating wildfires were blazing through the region. “I’d wake up in the morning and there would be ash all over my tent,” she remembers. “People who hiked about a month or so before me practically couldn’t finish. But luckily by the time I got there it was safe.” She ran dangerously low on water while trekking through the California desert (“I got so dehydrated that my hands weren’t working anymore,” she remembers). After being startled by a wasp’s nest, she almost lost her shoes down the side of a mountain, in an episode remarkably similar to a pivotal scene in Wild. (“Luckily, they didn’t go all the way down—I was able to retrieve them!”) She’d started a blog to chronicle the expedition, and in the face of blisters, fatigue, and hunger, the supporters she’d racked up encouraged her. “There was no way I’d let them down,” she says. “And right after my worst days on trail, I would have the best days.”

Thompson finished her hike October 11, nearly six months after she’d begun. But she was surprised to find that the end of the trail—the moment she assumed would be the most climactic—wasn’t in fact the highlight. “I didn’t have any kind of epiphany,” she says. “The most rewarding part, actually, was finishing each section. When I finished the desert, or when I did the Mount Whitney summit—the highest point in the 48 states—or going over a mountain pass in the Cascades in Washington, and just looking all around. Those were all moments that were more significant to me than the actual end of the trail.”

After stowing her hiking shoes, Thompson didn’t have a concrete plan—but she knew she’d fallen in love with Washington. Before she’d reached the end of the trail, a WeWork recruiter had contacted her with an opportunity in New York. To her delight, there was a position available in Bellevue too. She’d found a new home and experienced a major boost in self-assurance.  “I didn’t realize how not confident I was before,” she says. “But everything—even a workout—seems more manageable now.” The biggest transformation, however, was mental. “There were things I thought I cared about that I realized I didn’t anymore. I stress a lot less now because I figured out what’s important to me. I was always the person that rolled my eyes when I would hear people say [the trail is] life-changing. I’d nod, like, ‘I’m sure it’s great, but I don’t know about life-changing.’ But sure enough, it was.”

“There were things I thought I cared about that I realized I didn’t anymore,” says Thompson. “I stress a lot less now because I figured out what’s important to me.”

Another hike, though not yet on Thompson’s calendar, is a goal. “There’s the Appalachian Trail, and there’s another one called the Continental Divide,” she says of the treks she’d like to tackle. “Once you do all three, it’s called the ‘triple crown of hiking.’” The key to crossing such a behemoth of a goal off your bucket list, she explains, is refusing to let hesitation get the best of you. “I’m the perfect example,” she says. “I had no idea what I was doing. But you’ll always find a reason to back out. You just have to jump in and do it.”

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