By Sarah Alexander
When you look back on your life, you realize there are only a few key moments that have truly shaped it. It could be something substantial, like the school you apply for which defines your entire career, or a blind date you say yes to that results in a forever love. For me, it was the tiniest of moments: a text message from a friend about a job opening.
At 29, I was 8 months into some long-term travel plans, trying my hand at being an Instagram influencer and travel blogger. Though as much as I loved working for “exposure,” my funds had begun to dwindle, and I needed something more substantial—and consistent—to fund my remaining travel ambitions. The advertised role was fully remote, which, pre-work-from-home mandates, solved a problem I had been struggling with: how do you build a career on the road when traditional employment situations assume you’ll be in a particular building at a particular hour?
Honestly, the job of Content Manager for a luxury sustainable travel company felt too good to be true. It’s not often you come across a job listing that needs all of the skills you have, wrapped up in a remote role. What was this unicorn of a job? So, with a nothing-to-lose attitude, I applied, along with dozens of other hopefuls. With such high competition, I was not expecting much to come of it.
You can imagine my surprise when I received an invitation for the Zoom interview, which took place during my stint in Spain. After some liquid courage, in the form of a glass of vino, I had what must have been a successful interview with Dominique and Lana, as I was to start the following week.
I officially began in January 2019, six or so time zones away from the people I’d be working with daily. I didn’t yet fully understand that the time difference wasn’t a novelty; it was the foundation on which the whole relationship would be built, and it would be tested almost immediately.
At the end of the European portion of my trip, I flew to Dublin for 36 hours before crossing the pond to Canada, my next destination. I was entirely confident my flight out of the country left at 8 p.m. It did not. It departed at 8 a.m. The realization arrived the way these things usually do: with a sudden knot in your stomach while you’re happily going about your day.
Stranded on a backpacker’s budget, I checked back into the hostel as the clouds rolled in and the skies opened up. The moment felt a little too ironic. And yet, it worked out. Because the role was remote and I had my laptop, I was able to start my new job from a hostel common room over the following week. It was not the onboarding experience I would have designed. Still, it was an unexpectedly perfect introduction to what the role allowed: the ability to work from wherever I happened to be, and I mean wherever.
Later that year, I experienced Elevate from the other side—as one of their travelers.
After a last-minute opportunity arose, I drove eight hours to the San Francisco Airport and boarded a flight to Costa Rica for a 10-day Elevate trip. It was the first time I had traveled in that way: met at the airport, guided throughout, and able to move through a destination without the logistical anxiety that tends to accompany independent travel.
For the first time, I wasn’t thinking about transport routes, pricing negotiations, or how I would navigate meals with multiple food intolerances in a country I hadn’t previously considered accessible. Everything was handled with care and thought.
One evening, we released baby sea turtles into the ocean. I remember standing there, slightly stunned, thinking: it’s my job to tell people to do this.
This trip changed how I wrote about travel. I’d spent 6 months writing itineraries describing exactly this kind of experience for clients without having lived one myself. Feeling it, even briefly, gave me a much clearer sense of what we were actually promising people, and why every small detail of getting it right mattered.
After 18 months of travel, 10 of which were spent working for Elevate, I made it home to Melbourne, Australia, in October 2019. As you well know, a few months later, everything changed.
When the world stopped in 2020, my first assumption was that the role would disappear along with it. Travel companies weren’t exactly thriving, and I was newly arrived in an industry that had suddenly stopped moving.
Elevate reduced my hours, which was difficult, but they kept me on, which mattered more than I think I said at the time. Melbourne would go on to endure 262 days of lockdown, the longest of any city in the world.
During that period, having work, even in a reduced capacity, provided a sense of stability in an uncertain landscape. It gave structure to days that might have otherwise blurred together entirely, and a community to relate to, even if they were on the other side of the world.
I think that’s the part of remote work people undersell when they talk about flexibility and freedom: sometimes its value is simply that it gives you somewhere purposeful to show up, even when you don’t feel like leaving your bed.
By 2024, life had shifted again, but Elevate was still my rock. When I announced to the team that my partner John and I would spend a year traveling across North America in a van, I was met with excitement rather than the usual disappointment you’d get in a traditional work situation. There was no dread in sharing my dreams and plans, only ever support.
We traveled more than 30,000 miles across Canada and the United States. While John was on sabbatical from his job, I worked part-time throughout, often from the passenger seat while he drove—an arrangement John preferred, and I saw no reason to challenge. We had a booster antenna so I could get cell service in places that had no business having service. From the remote wilds of Alaska, to the top of Canada’s Northern Territories, and down to the Utah desert.
It meant I could keep working without needing to be anywhere close to an office, which, by that point, hadn’t existed for me in years anyway. The work didn’t need a desk. It just needed me, for a few focused hours each day, whenever and wherever I could find them.
That flexibility is hard to explain until you’ve been granted it. In Alaska, we joined a last-minute three-day sailing expedition through the fjords. I worked ahead, logged off, and disappeared entirely guilt free. We watched humpback whales breach beside the boat, kayaked past glaciers, and camped without signal or interruption.
When the sun was out, we adventured, and when the rain and snow came, I worked. I felt blessed to have such freedom. We camped above Exit Glacier, timing our adventure for clear skies, and watched the aurora move across the horizon from the entrance of our tent. In Utah, I worked from the back of the van at the Moon Overlook as snow fell outside, a small pot-belly stove keeping the cold at bay.
Work traveled with me, which meant the life around it could expand.
None of that was possible because the job was glamorous. It was possible because Elevate had built something more durable: a working relationship that never asked my location to stand in for proof that the work was being done. They asked because they genuinely cared.
The trust ran in both directions. Dominique didn’t need to see me at a desk to believe in the result, and I didn’t need to ask permission to step away from the desk when opportunities arose.
Over seven and a half years, I built a career with Elevate Destinations without ever needing to anchor it to a single place. I crossed continents without resetting my professional life; I carried financial security and a community with me instead. Twice, I returned home to Australia after long-term travel without the dread of having to start over.
But as they say, all good things must come to an end. As I move on from Elevate Destinations, what stays with me isn’t the list of places I’ve been fortunate enough to visit; it’s gratitude for being shown firsthand that this lifestyle is possible. Though it hasn’t always been easy, I now understand spontaneity is something work can absorb rather than something it punishes.
Many of the experiences that have shaped the past seven years would not have been possible without this role… or that one text message.
Thank you, Elevate, for the rare privilege of building a career that could move with me, wherever I happened to be, even when I didn’t yet know where that would be.
