How to Work Remotely and Travel

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!