Insta vs. reality: Deconstructing the digital nomad dream

Conversations on working from anywhere with Sam and Rachel

There are 3.5 million #digitalnomad posts on Instagram. It’s an endless scrolling vista of mountaintops threaded with clouds, pristine beaches at sunset when the shadows are long, bustling cities, and remote island getaways. You can almost feel the sand between your toes.

It’s the image of a lifestyle that was not an option to many of us before — but remote work has brought it closer to being within our reach.

Because now, we have borderless opportunities for work. We can choose to work on what excites us the most, rather than simply what’s available where we live. We have ownership over when and how we work — whether that’s 10 hours a week from a far-flung beach, or working night shifts to experience a new city by day.

But things aren’t always sunny when you’re WFA. We’re still figuring out what equity looks like in geographically distributed teams — financially and experientially. Work can transcend borders and time zones, but there’s an invisible wall the second we talk about employee rights, visas, and pensions. We don’t have all the right tools to connect with one another — and we’re still figuring out what great collaboration looks like when we’re scattered to the winds.

Also, sand is a real nightmare to get out of a laptop keyboard.

But most of all, we’ve realized that remote work offers us a freeing — and sometimes challenging — new reality. In today’s post, Sam and Rachel reflect on the lessons they’ve learned while working from anywhere — and why it’s not about the quest for an ideal.

“Remote work isn't about recreating an idealized Instagram lifestyle — it’s literally about building whatever you want.”

Sam Claassen, Head of Growth, Safetywing, Colorado, US

Sam was on a beach in Bali when he realized that there’s no right way to be a digital nomad. He’d gone there right after college to try the “typical digital nomad thing”, after a brief stint in a strip-lit office threatened to dull his sense of adventure.

“Remote work forces you to learn a lot about yourself really quickly,” he says. “I had one of those moments when the switch flipped in Bali. I was only working about 10 hours a week, and I was just surfing and hanging out the rest of the time. I realized really quickly that I’m not actually a beach person, and that I didn’t see an increase in happiness as I reduced the amount of work I did. 

“It forced me to take a step back and think, ‘what life do I actually want? What makes me happy? What should I be optimizing for?’ It wasn’t until I’d gotten started in this lifestyle that I’d even given that any thought.”

Sam didn’t figure out all of those answers immediately, but he had a pretty good idea of what he valued. Freedom to go wherever he wanted was high on the list — but he didn’t want not being tied to a location to cost him job satisfaction. Since then, home has been wherever he’s set his suitcase down for a spell — 66 countries and counting.

Right now, he’s in his home base in Boulder. But he could be anywhere, he says, he’d pick Slovenia, because “it’s like this hidden gem just tucked up away above Italy, where there are very few tourists.”

Ultimately, Sam thinks that if we’re going to get remote working right, it’s going to take a larger value shift for workers and companies.

“It’s about valuing outputs and results over inputs. When you’re remote, you’re not focused on how late people are in the office, how many meetings they’ve been in, or how much networking they’re doing — none of that actually matters. Because at the end of the day, nobody’s checking if you’re online on Slack. What really matters is: What are we achieving? Are we happy? How can we do more of what we love?

“Remote working isn’t about creating an idealized Instagram lifestyle — it’s literally building whatever you want.”

“I don’t want my freedom to be at the expense of my work.”

Rachel Coleman, Independent Education Consultant and co-founder of College Essay Editor, Malta

Rachel wanted to get into politics before she became a digital nomad. She started her career, fresh out of college, amid the neoclassical grandeur of the US Senate — “I thought I was going to get into politics and change the world!” — she says, wryly. She loved the work, but she didn’t love the long commute, the short holidays, or the thought of being confined to an office, no matter how grand and hallowed its halls.

So when she decided to start her own business, an independent education consultancy with her partner, she had one stipulation: that the work was 100% remote.

“I made this move into college counseling because I wanted to work with students all over the globe on their writing, and help them articulate who they are. But I can be anywhere in the world and still be fully employed, fully working — just in a different location.”

Eight years later, Rachel travels all over the world, leapfrogging time zones while running her consultancy out of Airbnbs and local rentals. Today, she’s in Malta. She’s got her sights set on Iceland next.

“There are two really important things for me,” she says. “One is that there’s this self-determination of running your own business. I set my own hours. I’m responsible for my own work. Being able to take ownership of that process is phenomenal.

“And then, there’s the freedom I think that comes with being a digital nomad, and saying, not only am I responsible for my work, but I’m responsible for my life. I’m responsible for the things that I value.”

Rachel sets her working clock by the West Coast, usually picking up her work in her Maltese home between 6pm and 1am. She spends the rest of her time immersing herself in the local culture, exploring, and making herself at home in places far from home.

“We have all these inherited social structures that say success looks a particular way — a big salary, or a leadership role. But I think a big part of the digital nomad ethos is saying that success is on my terms — you might value money, but I value time. 

“So much of life is about achieving all these ‘normal’ things we need to be functioning responsible adults, too: you must work, feed yourself, pay for healthcare, save for retirement. But the better question is, how do you do them — and do you do them on your own terms?

“Freedom, to me, is being the author of my own fate — the one who gets to live the best life I can, and doing the best work I can. I don’t want one to be at the expense of the other.”