Debunking the Digital Nomad Dream:What Remote Work Really Looks Like
One entrepreneur’s honest look at what the digital nomad dream really costs and gives back…
Emma Maidment is a wellness entrepreneur, international speaker, business mentor, podcast host, and author of Find Your Flow. Her work and story have been featured in leading publications globally. She helps leaders build magnetic personal brands and flow-based businesses that expand impact, income, and freedom. Co-founder of Flow States Collective & Flow OS, she mentors soul-led entrepreneurs to scale sustainably. Follow along at @emmamaidment_ for more.
Forget the dreamy laptop-on-a-beach Instagram posts. Remote work abroad looks nothing like that - unless you enjoy sand in your keyboard, a blinding screen glare, and Wi-Fi that cuts out mid-Zoom.
After more than a decade of living the ‘digital nomad dream,’ I can tell you this: yes, it’s incredible. But it’s also nothing like the glossy version you’ve been sold.
When I first pitched this article, I thought I’d be writing about timezone challenges, dodgy café Wi-Fi, and visas that require more paperwork than a mortgage. (And those things are real.) But what I didn’t expect to weave in was the darker, more complex side of living abroad as a mother, entrepreneur, and human being. Because the truth is, ‘living the dream’ comes with plot twists you’ll never see on Instagram.
Freedom ≠ Easy
Freedom has always been my north star. It’s the value that’s guided every decision since I walked away from the corporate world. I’ve built businesses, written books, birthed babies, and created homes across Berlin, Bali, and now Greece.
But here’s the thing no one tells you: location freedom is not the same as actual freedom.
You know those #officeoftheday posts with a laptop on a sunbed? Yeah, not a vibe. The screen glare is impossible, sand gets into places sand should never go, and everyone else is sipping cocktails while you’re trying to meet a deadline.
Real freedom is reliable Wi-Fi, a desk that doesn’t wobble, and knowing you can switch between ‘mom mode’ and ‘CEO mode’ without losing your mind.
Pro tip: Pay more for the Airbnb with the solid work setup. You’ll thank yourself every single day.
Parenting on
the Road
Add kids into the mix and ‘location freedom’ becomes a whole new game.
For us, it looks like homeschooling, working around nap schedules, and tag-teaming between deadlines and dinner. Some days it’s chaos. But it’s also deeply rewarding.
My kids are growing up bilingual, exploring new cultures in real time, and learning from the world - not a textbook. They’re also seeing two parents design life outside the conventional script, which feels like one of the greatest lessons we can give them.
It’s not always smooth (try sending an email while your toddler is attempting to spoon feed yogurt to a cat). But it’s ours.
When Life Happens Abroad
Here’s the part Instagram never shows: what happens when life goes sideways.
A week after I first pitched this piece, my husband ruptured his Achilles playing tennis. He was rushed into a Greek hospital where no one spoke English, and surgery was pushed before we had time to process. Thanks to local friends, we navigated our way into private care, but our insurance didn’t cover it. We paid out of pocket, grateful for the privilege, but shaken by the experience. Whilst eventually he found the right people to support him to heal naturally (yes, it’s possible) it took an immense amount of courage to advocate for that in a system that doesn’t understand.
Days later, I miscarried twins.
Nothing prepares you for grief like that - let alone in a foreign country, with two small kids in tow, unfamiliar systems, and language barriers.
This is the part no one glamorizes. The reality of handling medical crises, loss, and bureaucracy while still ‘living the dream.’
Why It’s Still Worth It
By now you might be thinking, “This woman is not selling me on the digital nomad life. Where’s the Aperol Spritz?”
But here’s the truth: despite the challenges, I wouldn’t trade this life for the perceived stability of a corporate office.
Because for every hard moment, there’s an equally expansive one. My kids are learning languages most adults struggle with. We’re building friendships and communities around the world.
When I was deep in grief and healing our local community rallied around our family. People we hardly knew. Even the lady who does my nails bought food over! A true testament firstly to the Greek culture and secondly to the importance of leaning in and creating community wherever you go.
Every day I’m grateful that we get to live fully by design, free from cultural pressures that once dictated what ‘success’ should look like. We may be foreigners, but that means no one expects us to follow the script. And that freedom, the freedom to write our own rules, feels like real success to me.
The Real Digital Nomad Dream
So, is the digital nomad dream real? Yes. Just not in the way Instagram sells it.
It’s messy. Unpredictable. Sometimes heartbreaking. But it’s also liberating, expansive, and
deeply human.
The dream isn’t about escaping life. It’s about creating one that feels true to your values - even when it’s inconvenient, even when it’s hard. So before you sell your stuff, pack your bags, and book a one-way ticket, ask yourself this: Am I chasing Instagram’s dream of freedom… or my own? Because freedom is your birthright. But it’s also your responsibility to build it, your way.
