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 development 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? Professional development? Personal enrichment? Passport stamps?



 Remote-Work Travel


Remote-Work Travel


Remote-work Travel 

Professional development opportunities


Social life


Wi-Fi security



Cost effectiveness





Saved time for logistics



Know-how sharing






Solo Remote-Work Travel

Those who venture out on a remote-work trip solo are generally hustlers and 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 WI-FI 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 & Co-working 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.


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 envisioned for myself in the beginning isn’t far from where I am now. I identified what I wanted out of my experience and what was important to me, which personally meant freeing up my time so that I could 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’re wanting and enjoy the f*cking ride. 


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We’re so confident in our community that we’re offering a money back guarantee on it.


The decision to request money back must be taken between the end of the first and second week after being an active member in our community. This is to give enough time to see if the program and community meet the expectations. The participant needs to actively attend events (at least 3 events per week). Qualifying official HP Events are

  • Monday Lunch
  • Goals Setting Sessions
  • Skills Sharing Sessions
  • Potluck

To set in motion, you need to both verbalize to the facilitators in charge and via email to [email protected] how and why we didn’t meet your expectations.


After following the steps above, we will calculate and refund your money. We will process back 1200 USD for a 4 week period, 2400 USD if you signed up for an 8 week period. You will be expected to leave the housing after the end of the initial two week period. You will receive a full refund for the trips that are more than 8 weeks into your initial start date.


This guarantee applies to dissatisfaction with the HP community on trip and other factors such as housing or weather will not be taken into consideration. 

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