Out of Office: Jill Caffey's “Everesting” Climb of a Lifetime

For Jill Caffey (Vice President, Property and Systems Administration), 2022 marked a year of pushing herself harder — both physically and mentally — than ever before. Having committed to compete in the Everesting Challenge with a friend the year prior, she traded in her running shoes for hiking boots and trained with cardio — every day for 365 days — for the day that would ultimately change her life.

Created by co-founders Marc Hodulich and Jesse Itzler, “29029” is the official name of “Everesting,” or in other words, climbing 29,029 feet — the vertical height of Mount Everest — within 36 hours. Jill and her friend Tara signed up for the event in Whistler, Canada, where the ascent is the longest of the “29029” mountains, with nearly 4,000 feet of vert per hike and requiring eight ascents to finish (with a descent by gondola in-between each climb). 

Photo: Jill Caffey

“Honestly, I knew nothing about what I was signing up for when I agreed to it,” said Caffey. “I’ve never even really been a hiker; I mean, I live in Florida. But I was going through some personal struggles at the time, and wanted something to focus on and work towards.”

While researching the challenge, she had many moments of doubt, and questioned backing out altogether.

“Something that stood out to me about the founders of 29029 and their methodology was that if you put life on a spectrum of one to 10, where one is extreme discomfort and pain, and 10 is the most exciting, pinnacle point, most of us are somewhere around five,” she said. “So many of us get stuck in our comfort zones just going through the motions. To push through and get to the ‘10,’ you’ve got to experience the ‘one’ — and I knew that’s where I wanted to be.”

To prepare herself for the 36 hour hike, she created a strict fitness regimen that demanded complete dedication and plenty of sacrifice — from missing out on time spent with friends and family, to 12+ hour, overnight workouts ranging from the treadmill and stairmaster in the gym, to strength training and running in the Florida humidity, and everything in-between.

Photo: Jill Caffey

After training as much as they possibly could, loading up their packs with the essentials (water, electrolytes, snacks, extra socks, etc.), Jill and Tara found themselves at the starting trailhead at 6:00 a.m. on September 23, 2022, where they began the journey of a lifetime alongside 250 other hikers.

Committed to staying together and keeping each other accountable throughout, the duo hiked the coastal rainforest terrain of the Blackcomb Ascent Trails through scenic forested sections, crossing bridges over small creeks, and up ski hills from Whistler’s valley bottom to the alpine on Blackcomb Mountain — over, and over again.

33 hours and zero sleep later, they were among the 67% of participants to successfully finish the challenge.

Photo: Jill Caffey

I probably underestimated how powerful I’d feel and how proud of myself I’d be at the end,” said Caffey. “I think in the back of my head I knew we could physically do it, but it was far more mentally challenging than one could imagine. At the end, it was so incredible to hear them call out our names across the mountain. After such a challenging year in my personal life, it was an amazing reminder that I can do hard things, and when life throws me an obstacle, I can get through it.

Immediately following the climb, they attended the awards ceremony, then proceeded to sleep for the majority of the following day, before heading home to Jacksonville.

“Your brain is really one of the most powerful muscles you can flex,” she said. “To be able to know that under adversity, I can lean on my mental toughness, is something to be proud of. It’s the best feeling ever, for sure.”