This 20-year-old Won a Travel Dream Job — Here's What It's Really Like

Jackson Lebsack is an easy guy to be jealous of. After all, he’s charming, athletic, and getting to travel the globe for a living. Oh yeah, and he’s only 20 years old. Though it may seem like success just fell into his lap when he was hired for Ski.com’s Epic Dream Job in late 2018, he’s certainly earning it now. And I don’t mean by punching the clock every day. His hours and duties extend far beyond the traditional 9-to-5.

I tagged along with Lebsack for a few days in Switzerland and France as he started his new gig to learn what getting hired for a dream travel job is really like. And for him, it includes hiking for hours in the backcountry of Verbier before sending it down a vertical, eating more cheese than most people would find appropriate, and spending time with a few adoring fans.

“I just have to get my drone,” Lebsack said as we made our way out of the boundaries and into the backcountry at Verbier, a mountain town in Switzerland beloved by the likes of celebrities like Richard Branson. We were there as part of the fourth stop of Lebsack’s two-month tour of more than 18 ski destinations available on the Epic Pass.

So, we kept trudging ahead as he dug out his equipment. Putting one foot in front of the other, our group made our way up the craggy hillside and soon enough heard the whirling of a drone overhead. Though it felt like we had put quite a distance between ourselves and Lebsack with our hike, which also caused just a glisten of wintry sweat to come across my forehead, moments later he appeared with a grin from ear-to-ear as he extolled both the awesomeness of the drone shots and the scenery around us.

Finally, we reached the summit. While I was busy looking over the edge with trepidation, Lebsack was busy strapping his GoPro to his head, hastily throwing on his skis, and telling everyone how he was going to do a front flip off a nearby rock. I thought he was joking. He was not.

And, remember, this is all actually a part of his job description.

“We weren't looking for somebody to make a ski movie, we were looking for somebody to tell a story about what it feels like to be in the destination,” Dan Sherman, the chief marketing officer of Ski.com, shared about what exactly they were looking for in the hire.

If anyone would know what it takes to deliver on a dream job, it’s Sherman. After all, he too has the dream career and even got to tag along with Lebsack on the first part of his travels through Stowe, Vermont, St. Anton, Austria, the Dolomites, Italy, Verbier, Switzerland, and Courchevel, France. In total honesty, the pair really should be completing the entire world journey together. Though Sherman is twice Lebsack’s age, they're like the protagonists in a buddy movie everyone would watch. Sherman doled out handy life advice to the young filmmaker left and right including essential tips like “order burrata every time you see it on the menu” and carefully curating the perfect ‘90s hip hop travel playlist.

Following the day of hiking and skiing, I joined Lebsack and Sherman to continue filming at a little bar just down the hill from the mountain. As we bellied up, a man wearing a Colorado hat approached, gleefully reaching out his hand to ask if Lebsack really was the Ski.com dream job hire.

“Yeah, that’s me,” Lebsack said with a smile, happily shaking the man’s hand and explaining his job to him. “I wanted to apply for that job, but my wife would kill me,” the well-wisher replied.

After the encounter, I asked Lebsack just how remarkable it must feel to be recognized.

“It’s actually not the first time,” he said with a laugh.

Following the bar, we went across the street to take part in a true Swiss tradition: stuffing our faces with raclette. Though, as we ate, Lebsack buzzed around like a bee taking photos and videos, even disappearing for a moment into the kitchen and laughing along with the restaurant manager as he held up a block of cheese for a picture.

Really, Lebsack was sort of born to fill this role. After all, his dad worked for a ski gear company, and he grew up in Hood River, Oregon, an outdoor mecca with plenty of mountain activities to fill a kid’s day.

As a teenager — which, remember, for Lebsack was just a short time ago — he picked up a camera and just started taking photos and videos of his friends. He knew right then and there that this was the path for him. He enrolled in college in Montana, where he went to school for a few semesters, but soon realized his own skillset outpaced his teachers.

In the spring, Lebsack made the decision that college simply wasn’t for him and it was time to get to work instead. In the months that followed, he made a steady living filming weddings and producing a 20-minute documentary in Nepal in conjunction with the clothing label Vindur Hao.

Then, in October, Lebsack heard about the job to end all jobs.

“I heard about it through Andrew Muse,” Lebsack explained. “I saw on his Instagram story, ‘It’s the last day to enter Ski.com’s dream job.’”

But, because it was the very last day the company was accepting entries, Lebsack thought twice. To apply, he would have to create a video proving he was the best fit. He almost didn’t go through with it. But, in the end, he dropped everything and went for it.

“I really liked his narration,” Sherman noted of Lebsack’s last-minute entry. “Internally I was calling him Ferris Bueller because of it. The video was really cinematic and just screaming wanderlust to me and that's what we're looking for.”

Out of more than 1,100 applications, the team at Ski.com knew he was it. So, they hired him. That was the easy part. Now, it’s up to Lebsack to succeed.

The idea of getting hired for a dream job sounds like, well, a dream, but in reality, there’s a lot more to it. Sure, Lebsack gets to play in the snow all day, but from what I saw he also needs to possess some sort of super-human strength to also stay up all night cutting video and editing photos.

As part of the work, Lebsack gets to go out and experience the mountains, the towns, and the après-ski scene. Then, he must cut a 60-second video for each location, along with providing the Ski.com team with several photos of his daily adventures for social media.

After the trip is complete, Lebsack will also cut two-minute regional videos including Europe, Japan, Canada, and America. He will also likely be cutting a full-length video from the entire trip. And, in case you’re not familiar with the craft, let me be the first to explain that this is a monumental task. However, it’s one Lebsack does not only with ease but also with pure enthusiasm.

“It’s been pretty manageable,” Lebsack said of the job. “It's definitely a lot of work. We play, play, play all day, which can be super draining when I realize I have to go and edit. But, then I think about, well, everyone my age is sitting in a classroom right now and doing that all day instead of this. And then I get really motivated.”

Of course, there is a little bit of fun thrown in there too. On the way from Verbier to Courchevel, France, we pulled over to take one perfect run down the mountain at Chamonix. Because, well, why not? We were living the dream job. Then, we checked into our hotels in Courchevel, which included the absolutely ritzier than ritzy Hotel Saint Roch, a five-star hotel that regularly hosts the world’s top royalty, and the Annapurna, another five-star resort with ski in, ski out access. As we sat by the pool at the Annapurna, I asked Lebsack what he thought he’d be doing by the time he’s 25 thanks to this gig. Lebsack looked off, reached up to rub his temple, and laughed.

“By the time I'm 25, who knows what's going to happen. Just today I woke up and took a helicopter ride and then paraglided all before lunchtime. It was pretty ridiculous. But you know, I have no idea. I hope it continues. I'm so grateful for everything that's happened so far.”

Follow more of his adventures on Ski.com and its Instagram channels here. Maybe, just maybe, it will inspire you to go after your dream job too — no matter your age.