Now That I’m a Digital Nomad, I Don’t Take True Vacations Anymore

Becoming a digital nomad is a dream come true for many. The freedom to work from anywhere in the world, experience new cultures, and meeting diverse people are just a few of the perks. The ability to work from your laptop in a cozy Buenos Aires café one week and a beachside bungalow in Bali the next feels like the ultimate in work-life balance. But there’s a flip side to this freedom—one that I didn’t fully anticipate until I was well into my nomadic journey. Now that I’m a digital nomad, I don’t take true vacations anymore. 

Let me caveat this by saying that I am a freelancer. (I probably should’ve said this at the beginning.) While there are now a plethora of full-time fully remote jobs with paid vacation  available, I’ve been trying to avoid any job that requires me to officially ask for permission before taking time off. I figured if I was leaving the office altogether, I should also escape the more of the rigidity that comes with full-time employment. Well, as you might guess. More freedom comes with some trade-offs.   

The novelty of being in a new place and visiting an iconic landmark in the middle of a workday can certainly make work feel less like work and more like play. However, this constant integration of work and travel has a downside. I’ve found that I rarely, if ever, take a true vacation—those blissful stretches of time where I ignore work emails, put my projects on hold, and solely focus on relaxation and recharging. Instead, even when I’m in the most beautiful places, I’m often tethered to my laptop, sneaking in work sessions between sightseeing or even while sipping a cocktail by the beach. The irony is that, while I’m in these dream destinations, I’m not truly disconnecting in the way I would on a traditional vacation.

This issue becomes most challenging when friends come to visit. They arrive ready to unwind and explore without a care in the world, while I’m trying my best to be a great tour guide and also juggling deadlines, Zoom meetings, and being a tour guide. They can fully immerse themselves in the experience, while I’m only half-present, my mind never fully able to get away from work. I must admit that I envy them and that FOMO is real. They can leave their responsibilities behind, while mine follow me wherever I go.

Has this happened to anyone else? Or do I just feel this way because I am American. The nature of freelancing and remote work means there’s often a pressure—self-imposed or otherwise—to always be available and always be producing. The flexibility of being able to work from anywhere often leads to working everywhere.

So, I’m curious—can you manage to take true vacations as a digital nomad when many days already feel like part of them is vacation? It’s funny that the freedom that comes with being a digital nomad can sometimes result in less truly free time than you had during your time as an employee. I’d love to hear you have handled this challenge how others handle this challenge and if you’ve found any effective strategies for truly unplugging. Maybe we can find some balance together.