From Manhattan to Death Valley to 30A and beyond, Jillian Rebekah conquers one unpaved trail at a time.
Jillian Rebekah often encounters obstacles she is not sure she can overcome.
The 40-year-old lives a life she never imagined for herself, but it has helped her find meaning and purpose. In turn, she has inspired countless others to seek and overcome challenges in their own lives.
It all started with a pickup truck. Specifically, the tan Toyota Tacoma she bought for herself in 2016, after returning to her childhood home in Southern California. As a recent transplant from bustling Manhattan, where she and her husband had kept a tiny sedan tucked in a garage, the truck was a significant shift. But she was spending more and more time exploring mountains and deserts. And there were places she just couldn't access. She needed the power of a four-wheel drive.
Kennedy Meadows
Seemingly endless trail systems wound through the Eastern Sierra Nevada Mountains, about four hours from where she lived. The trails explored all around Mount Whitney, the tallest peak in the United States outside Alaska, and across Death Valley, the lowest point on the continent.
"The diversity in the area is huge," said Jillian. "That was my playground almost every weekend. I was out there just exploring, but I was also seeking something."
She recalled a pivotal moment not long after she bought the truck when she had been exploring Kennedy Meadows, high in the mountains, moving her truck through terrain that challenged her. She was miles from civilization, scared she would get stuck, and wondering how on earth she would get out of it. It's rough on the truck, but also on the mind and body of the explorer behind the wheel.
"You're putting yourself out there, far away from all the normal safety nets we have," she said. "You're on your own. There's some fear involved."
Finally, she made it to the end of the trail and discovered an astounding view that took hold of her — the way the sunlight filtered through the trees, the sound of a stream trickling nearby. She was hooked.
"It was this incredible moment where I just felt like, 'Oh, this is what I'm going to do,'" she said. "I'm pursuing this. Whatever I need to morph into to get more of this, that's what I'm going to do."
Jillian said she has learned to combine the experience of these impressive natural phenomena with the relief and pride that comes with challenging herself, overcoming her fears, and conquering obstacles. That sweet spot is where she feels closest to life's meaning.
Still, she had no idea that within a short time, she would be swapping suspensions, trading bumpers, and adding gear ratios to her motor, much less getting a rooftop tent for sleeping in her truck, taking days-long trips to remote locations, leading women-only camping excursions, and becoming one of the top influencers in the overland adventure industry.
"I kind of accidentally fell into this whole thing, which makes it really fun," she said. "It feels authentic."
A sharp right
In 2011, Jillian and her husband, who have been married for almost 20 years, had hit a rocky place in New York. He was climbing the ladder in the financial industry and had landed a coveted gig on Wall Street, but the couple realized the life they had been working towards was not as dreamy as they had imagined. There was no joy or fulfillment. They needed to find their way back to each other and out of the mess they'd made.
Jillian was asking questions: How am I living my life? What example am I setting? Where is the meaning? What do I want the meaning to be?
They made a break for it, desperate to try anything to keep themselves and their marriage intact. They moved back to Southern California and started piecing things together. At first, they hit the trails side-by-side, but it soon became apparent that this would be Jillian's thing. It was a calling, and she set out more on her own.
Overlanding, or taking long off-road treks, began decades ago in Australia, parts of Asia, Europe, and South Africa. In the United States, it has enjoyed a significant boom over the last five years, with people setting out on adventures in everything from pieced-together junk vehicles to multi-million-dollar trucks explicitly designed for the purpose. Trips range from overnight to months at a time.
"The vehicles let us drive hundreds of miles off the highway to explore a new mountain range," Jillian said. "We're finding these new ways to escape the city and the rat race and the craziness of our heavily connected lives. And, as cliché as it sounds, you really are finding yourself again."
As one of the few women in a tight-knit and mostly male community, when Jillian started posting pictures of her and her truck on social media, she got noticed. People began urging her to take her explorations farther. As she did, she realized she had a message to share with others who were already into overlanding or might be interested in taking a leap in their lives, whatever that may be.
It's never too late to re-evaluate, ask questions about your life, make big changes, or take a sharp right turn. "If you felt like you just went through life and colored in the lines for the last 20 years, and now you are wondering, did I waste my life? No, you didn't," Jillian said. "I waited until I was 35 to find this."
Into the unknown
Since then, Jillian has taken many trips, including down to the border of Mexico, across West Texas, and her longest excursion, 25 days on the road up to Washington state.
The challenges are real. Jillian has encountered shelf roads where she felt she would slide off or flip her truck. She hit rain storms that seemed beautiful until she realized the water turned the road into mud. And not the right kind of mud — the snot kind of mud where she wondered if she'd ever get back to civilization. A man brandishing a knife crashed one of her women-only campouts, and she had to go into mama-bear mode to convince him to leave. Once, she accidentally camped in the middle of a caravan of migrants being smuggled into the country overnight.
"You have to learn how to handle yourself properly," she said. "You have to be as well trained as you can and be aware of your surroundings in a way you maybe weren't before."
Today, Jillian is still driving that tan Tacoma. She leads her Ladies Night Campouts, as she has for the past five years, helping to forge dozens of friendships and give women the confidence to set out on their own. She has over 45,000 followers on her Instagram page (@jillianrebekah), and she has her own podcast, Citizen J, in partnership with Storyteller Overland.
When she's not doing all that, she can be found on the trail, pushing herself, scaring herself a little, taking in those moments of pure joy, and sharing them with others.
"I get to watch people go, 'Oh, I'm going to go try something new, because I watched you do that. And it wasn't that scary, and you got to the other side of it, and it didn't kill you. Now, I have some encouragement to go do it my way.' I think we all need each other in that way."
Story by Lauren Sage Reinlie.
To learn more about Jillian, visit citizenj.com or follow her on Instagram (@jillianrebekah).
Originally published in Beach Happy Magazine, Issue 12 — Spring 2023.
