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Instagram has 3.5 million #digitalnomad posts, each painting a picture of a dream lifestyle—cloud-kissed mountaintops, sunlit beaches, vibrant cities, and remote island escapes. You can almost feel the sand between your toes.
Remote work has made this once-unattainable reality feel closer than ever.
- Borderless work opportunities mean we can choose jobs based on passion, not just location.
- Flexibility over time and place allows for 10-hour workweeks from a beach or night shifts to explore a new city by day.
But the WFA (Work From Anywhere) life isn’t all sunsets and surfboards:
- Equity challenges exist in distributed teams—financially, legally, and experientially.
- Borders still matter when it comes to employee rights, visas, and pensions.
- Collaboration is evolving as we navigate new ways to stay connected across time zones.
- And yes, sand in your keyboard is a real struggle.
Ultimately, remote work isn’t about chasing an ideal—it’s about embracing a new, freeing, and sometimes challenging reality.
In today’s post, Sam and Rachel share their biggest lessons from working anywhere—and why the goal isn’t perfection, but balance.
“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’s Take on Remote Work: Finding What Really Matters
Sam thought he’d found the perfect digital nomad life—working 10 hours a week from a Bali beach. But reality hit fast:
- More free time ≠ more happiness – Surfing all day wasn’t fulfilling.
- Self-discovery happens fast – Remote work forced him to ask, What life do I actually want?
- Freedom is key, but so is purpose – Being untethered didn’t mean sacrificing job satisfaction.
Since then, he’s explored 66 countries—but it’s not about the destination. It’s about shifting how we work:
- Focus on outcomes, not appearances – Forget office hours, meetings, or networking optics.
- Success isn’t about looking busy – No one’s tracking your Slack status; results matter more.
- Remote work isn’t an Instagram dream – It’s about designing your version of an ideal life.
Right now, Sam’s in Boulder. But if he had to choose? Slovenia—because it’s a hidden gem “tucked above Italy, with barely any tourists.
“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 started in politics, working in the US Senate, dreaming of changing the world. But office life—long commutes, short vacations—wasn’t for her.
So, she built something different: a fully remote education consultancy. Now, eight years in, she runs it from Airbnbs across the globe—today in Malta, tomorrow maybe Iceland.
Her two biggest lessons?
- Owning your work = owning your life – Setting her own hours, taking full responsibility.
- Success isn’t one-size-fits-all – It’s not about salary or titles. For her, time matters more than money.
She works on West Coast hours (6pm–1am in Malta) and spends the rest of her time living. Because real freedom isn’t just working from anywhere—it’s choosing how you work and live, on your own terms.
