3 Realistic Ways to Travel the World while Working Remotely

3 Realistic Ways to Travel the World While Working Remotely

When I first heard about the remote-work-travel lifestyle, there were definitely visions of Mojitos on a beach (“no sugar pls”), my laptop beside me proudly displaying a fresh software update, as I cool off from the professional breakthrough I had just made (as a result of being more productive and inspired). But the further I researched, the more I realized that this wasn’t the reality for errbody — or even the vision. ‘Remote-work and travel’ means different things to different people.

What’s there to gain from a remote-work trip?

After going a little deeper, I found that some people were looking to “nomading” as a way to live cheaply in destinations with favorable currencies. Others were looking to explore new cultures and expand their personal/professional networks. The rest seemed to be keen on racking up international memories with a friend or partner in a sustainable way.

Margaret working at the pool.

With no one way of going about it, if you are new to the concept of location independence and want to get into traveling while working remotely, a good place to start is by outlining your goals; what you are wanting to achieve by adopting this new lifestyle. Let’s break down the three most common approaches.

Solo Remote-Work Travel

Those who venture out on a remote-work trip solo are generally hustlers. They aren’t afraid of getting their hands dirty — and they do. They are more than happy to put equal amounts of time towards life-maintenance, trip struggles (*read as: THE WIFI IS DOWN AGAIN*) and working while on the move. Making those monies stretch as far as possible is often a priority — sometimes at the expense of convenience.

They get sh*t done, and seem to manage it all, but don’t get as much exposure to professional development opportunities as others. There’s only so much you can plan/research when you’re single-handedly doing life, planning a trip in an unfamiliar destination, and upholding a job.


Group Remote-Work Travel

People who join remote-work travel groups are generally very career-driven. They want to experience new places and meet new friends, but before anything, they want to get kick-ass professionally. That means that it’s common for them to allocate a portion of their monthly budget to a specialized company that:

  1. Provides a built-in community for the fun stuff (exploring) and the professional stuff (skill-sharing, etc).
  2. Deals with trip logistics (accommodations & coworking space) and travel-related struggles (getting sick in South-East Asia is something different), and
  3. Plans networking/workshops/cultural/social/wellness events, so you don’t have to.

But is this where you get the most bang for your buck? If your “bang” = focused time on building your career, then yes ma’am.


Buddy Remote-work Travel 

This one is somewhere in between. Doing a work-travel trip with a friend/partner can be very comforting, so it’s understandable that people attempt to make this happen. The problem is that it can be difficult to coordinate, not only your own travel/work requirements but then those of your buddies too. That being said, it is cost-effective and you won’t need to rely on making new friends as much for social interaction. Two/three heads are better than one when it comes to finding professional development opportunities and taking care of logistics. But then again, it will still take away time from your work, albeit less if you’re working together.

A Remote-Work Comparison

Solo Travel  Group TravelBuddy Travel 
Professional development ✔️✔️
Social life✔️✔️
Wifi security✔️
Living cheaply✔️✔️
Time saved on logistics✔️

The Bottom Line

My research into remote-work travel options began and ended a long time ago. I’ve been doing the global rounds, working remotely for almost 3 years now. And honestly, what I had initially envisioned for myself isn’t far from where I am now. I identified what I want out of my experience and what’s important to me, which personally means freeing up my time so that I can focus on my work and the adventure on the ground, not logistics and translation issues with dodgy accommodation hosts.

My advice: know what the limitations are for each of the approaches, and know what you are getting in to. From there, put your effort towards the outcomes you want and enjoy the f*cking ride.

Thinking about joining a remote-work community? Check out where Hacker Paradise is headed next!

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