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How to Work Remotely and Travel

In the post-COVID world, remote work remains extremely common. Plenty of people want to combine this situation with getting out and seeing the world (we don’t blame you!). So, we’ll use this article to outline our steps for how to work remotely and travel. 


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In addition to writing about his and Jenna’s travel and work adventures, Chipp is a CPA and founder of Walutes Capital, a real estate development and accounting firm. Wearing this “other hat,” Chipp offers real estate investment and development consulting services to clients. If you’d like help with your own real estate investing journey, contact Chipp here to set up an appointment! 

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Step 1: Define Your Remote Work


Before heading overseas to work remotely, you need to actually define what you’ll be doing for remote work. Your work responsibilities will provide left and right lateral limits to how you can travel, so it’s important to outline exactly what you mean by remote work. That is, how will you answer these three questions:


  • Who will pay me while working remotely - an employer or clients?  

  • How much can I expect to get paid for my remote work?

  • What limitations on my time will remote work impose while traveling?  


Broadly speaking, two options exist to answer these questions:


Option 1: Continue in your “traditional” remote work capacity. If you have a 9-to-5, W-2 job that allows you to work remotely, you have significant financial flexibility to travel. That is, you know that every two weeks, you’ll get a paycheck deposited, meaning you won’t have to stress about generating cash flow while traveling. But, the inherent drawback to this approach is that you’ll still be working 40-hour weeks tied to your employer’s timelines and other job requirements.  

Option 2: Conduct freelance / self-employed work. On the other end of the spectrum, you may want to head out on your own, operating as a self-employed freelancer. This option gives you significantly more travel flexibility, as you’ll define your own hours and responsibilities. But, the inherent drawback here is that, what you gain in travel flexibility, you lose in financial peace of mind. As your own boss, you only make money when you earn it - gone are the days of bi-weekly direct deposits.

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Step 2: Define Your Travel Style


Once you’ve confirmed what your remote work will look like, you need to define how you want to travel. Again, we recommend answering a few questions to guide your planning: 


  • What do you want an average week to look like while traveling?

  • Will you be traveling to cities, rural areas, or some combination, as this will likely affect wi-fi access? 

  • Do you plan on staying in one place for a long time, or seeing a lot of places for shorter periods? 

  • What sort of lodging do you want to use (e.g. AirBnB, long-term local apartment rentals, hostels, hotels, camping, etc)? 

  • What are your travel priorities (e.g. getting to know local traditions and routines, local cuisines, adventure travel, exploring museums, etc)? 


Two ends of a dynamic spectrum exist here:


Option 1: Replicate home life - just while traveling. With this option, you basically replicate your remote work routine from home in a different place. For example, say you live in Southern California and work from the second bedroom in your apartment. Instead, you move to a village on Croatia’s Dalmatian Coast, rent an apartment for six months, and work from the guest bedroom there. Now, instead of spending your evenings and weekends in California, you spend them in Croatia. The option provides a sense of stability and lets you really get to know an area, but you don’t necessarily take full advantage of traveling. In other words, the emphasis here is on work more than travel


Option 2: Travel, travel, travel, and oh yeah, do a little work. On the opposite side of the spectrum, you embrace the remote part of remote work. With this approach, you build a travel itinerary and priorities for things you want to do, and then you see where you can squeeze in a little work along the way. Clearly, this option forsakes stability for the opportunity to go out and see the world. Rather than continuing your remote work life in a different location, this option turns remote work on its head, allowing you to get on the road while working a bit to pay the travel bills. 


Practically speaking, you don’t have to fully embrace one or the other option. Instead, as stated, your travel style exists on a spectrum, likely falling somewhere in between the above extremes.

Chipp working remotely while traveling in Zanzibar

Chipp working remotely while traveling in Zanzibar

Step 3: Develop a Plan to Align Work and Travel


Next step? Reconcile your remote work and travel plans! Does any disconnect exist between 1) how you plan on working remotely, and 2) how you envision life on the road? At this point in time, you have to connect the dots, developing an executable plan for both working remotely but also achieving the goals of your travel. If you can’t hit your travel wickets, what’s the point of leaving home? 


For example, work-wise, we embraced a hybrid of full-time, W-2 work and freelance contracts. Jenna transitioned from her role as an employee to a contractor with her company. In this respect, she held many of the same responsibilities but worked a maximum of 20 hours every week. However, at times this required late-night calls to balance our timezones with client and company timezones. On the other hand, Chipp solely worked as a freelancer, knocking out project-based contracts not tied to any specific timezone. Every week, Chipp had certain tasks he needed to complete for clients, but he could do them whenever he wanted.  


From a travel perspective, our priority was living in cities overseas, learning the local cultures, and developing daily routines in another city. At a minimum, we’d spend two weeks in a single place (and ideally longer) to establish a bit of a routine and get a decent feel for the area. To combine this philosophy with our work situations, we settled on a rough schedule of working Mondays to Thursdays through early afternoon. Jenna typically worked from whatever apartment we were renting, and Chipp would find a nearby co-working space. After wrapping up work, we’d head out and explore the city we were currently living in, walking all over the place, eating at neighborhood restaurants, and just embracing life as aspiring locals. This approach had the added benefit of giving us three-day weekends for little getaways. And, when we wanted to do longer trips (e.g. a Tanzanian safari), we just coordinated with our former employer (Jenna) and clients (Chipp) to take a week off work to focus 100% on travel. 


Bottom line, no correct answer exists to how you should balance work and travel. But, by going through the exercise of 1) defining your remote work situation, 2) considering how you want to travel, and 3) building a plan to connect the two, you’ll set yourself up for success in your adventures. 


Step 4: Confirm Remote Work Admin and Logistics Requirements 


Building the above travel and work plan is the fun part. Unfortunately, though, no plan will succeed if you don’t consider the detailed admin and logistics requirements of remote work overseas. Before leaving the comfort and reliability of your own home office, we highly recommend building a checklist of all those seemingly little things that, if ignored, could derail your remote work plans. While not a comprehensive list, here are some items to consider: 


  • Time zones: How will different local times affect any required remote work coordination?  

  • Wifi / power reliability: Do the places you plan on traveling have reliable wifi and power sources? If not, do you have a back-up battery and wifi hotspot?

  • Log-ins / IP addresses: Do the remote work websites and software you use require log-ins from a specific IP address location? Will these work without a VPN while overseas? 

  • Virtual private network (VPN): Do you already have a VPN for overseas travel? Signing up for one is critical for 1) digitally protecting yourself on unsecured wifi networks, and 2) allowing you to change the location of your IP address (e.g. use a US-based IP address while traveling in Southeast Asia).

  • Overseas phone plan: Do you have a way to talk on the phone and use data while traveling? Getting an international SIM card is a must.

  • Laptop portable monitor: Does the work you do require a second screen? If so, you’ll likely need a portable monitor for your laptop

  • Do you need any additional computer equipment for your remote work? 

  • Office / co-working requirements: Will your work require you to spend any time in a physical office or co-working space? If so, have you identified some potential options in your different travel destinations? (NOTE: Chipp absolutely loved overseas co-working spaces. In addition to being more productive in an office-type setting, he met tons of interesting people in these spots). 

  • Visas: Do the countries you’re visiting have visa requirements? If so, have you completed any associated tasks before leaving home? 

  • Medical / vaccine requirements: Some countries also have medical and vaccine requirements prior to arrival (e.g. having your yellow fever passport). Have you completed these items? 

  • Mail processing: How will you handle your “snail mail” processing back home? Do you have a friend or family collecting items, or will you use a professional mail processing service? 


Once again, the above list isn’t exhaustive. But, the important takeaway here is to go through the detailed planning necessary to turn a good remote work and travel idea into a practical plan


Good luck, and have a blast on the road!

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Affiliate Disclosure


We’ve included affiliate links on this page. If you click on a link and end up buying something, we may receive a commission (without adding any costs to you). This helps us pay the bills, and we only promote products and services that we personally use and wholeheartedly endorse. Thanks so much for the support!


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