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How to work remotely while traveling

by Ashley
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How to Work Remotely While Traveling: Avoiding Burnout and Embracing the Adventure

I cannot tell you the number of times that people tell me that they wish they could travel like we do, that they could work while traveling. I’m here to tell you that you can! If you want to, and you have the means and a job that allows remote work, you can

There are a number of potential challenges to consider when planning to work on the road – from arranging pet sitters or planning around your childrens’ school schedules to dealing with medical situations or sticking to a budget. The challenge I want to focus on in this post is the actual art of working while traveling. 

For context, I have never had an in-office job. I’ve been working remotely since college, with both 1099 and W2 jobs. I currently have a day job doing learning and development work for an insurance company. Growing up in an entrepreneurial family helped cement the idea that work can be done from anywhere, and that travel doesn’t always have to be a vacation. 

So I’ve been taking my work with me and working while traveling for more than half of my life; in many ways it comes natural to me but I’m also always learning. As technology and work cultures evolve, we must also make changes to adapt. I hope that by sharing some of what I’ve learned over the years can help you in evolving how you think about travel and give you the tools to feel empowered to take on the challenge of working remotely while traveling.

In my experience, the biggest challenges to working while traveling are having an adequate dedicated work space including fast, stable wifi; maintaining a healthy work-life balance in unfamiliar locations; and trying to do too much and burning out. 

Let’s explore how you can effectively work remotely while traveling, without succumbing to any of these problems. With some strategic planning and a few key tips, you can still kick ass at work AND maintain a healthy work-life balance while enjoying the thrill of exploring new places.

Stop thinking of “travel” as “vacation”. They are not the same.

First and foremost, it’s crucial to shift your mindset and differentiate between travel and vacation. Vacation is all about relaxation and rejuvenation, taking time off work to do something you want to do, and does not necessarily involve going anywhere. When we talk about travel, we mean the experience of immersing yourself in new cultures and destinations.

By understanding this distinction, separating the idea of ‘vacation’ or ‘not working’ from the idea of travel, then it becomes easier to travel around your work.

For example, when we spend multiple weeks in a location, we work a regular Mon-Fri schedule, for the most part. We may take a couple days off to give ourselves a long weekend, but we are not dramatically changing our daily routines regardless of our geographic location.

Consider time zones.

When working remotely, time zones become an important factor. And boy, can it be easy to mess them up! (Speaking from personal experience, ha.) Be mindful of the time differences between your current location and your clients or team members. Plan your work schedule accordingly, allowing for productive overlap while also allowing yourself to enjoy the local surroundings during off-hours.

For example, when we stayed in Mexico for over a month, we were living and working in Eastern time while our coworkers lived and worked in Central… until the US switched over to Daylight Savings Time, which Mexico does not observe, and we were suddenly back in Central Time. Like I said, time zones can be hard! 

For us, we prefer to stay within 3 hours of our coworkers. This prevents us from having to work odd hours or late at night. We have a child, do we want to maintain a consistent, usual daily flow close to what we do at home. If we did not have a child, we would both be more amenable to working odd hours; we know several digital nomads who travel extensively through Europe and Asia, requiring them to work late at night to have overlapping time with their coworkers. If that works for you, great! But if, like us, you have a kid (or multiple), you will likely want to travel to a timezone that makes working remotely easy. 

Don’t live on a laptop alone.

To enhance your remote work experience, invest in tools to expand your screen real estate and care for your hands, like a Sidetrack, an external monitor that attaches to your laptop, and a portable keyboard and mouse. These accessories can improve ergonomics and productivity, making your work hours more comfortable and efficient.

I am *obsessed* with the Sidetrak monitor. It’s lightweight, easy to pack, plug-and-play simple to use on Mac or PC, and even though it’s a lot smaller than my curved monitor at home, it is a game changer for working remotely while traveling. 

Create an easy-to-pack workstation.

Designate a specific bag to keep your work essentials organized and easily accessible. The first essential piece is a laptop backpack that you love. Find one that will hold all of your necessary electronics and a few essentials. I’m able to easily and quickly pack both my work and personal laptop, my Sidetrack, my mouse, earbuds and Airpods, plus any other small electronics like my Kindle and various charters. I can pack up or unpack in under 5 minutes. Having a well-prepared workstation will make it hassle-free to set up and start working wherever you go, whether it’s a semi-permanent setup at your AirBNB or hotel or if you go to a co-working space.

Be strategic with your PTO.

Working remotely while traveling allows for flexibility in your schedule, and while you don’t need to take time off to travel while working remotely, you can maximize your time in a destination by strategically planning your time off

Holiday weekends give you a freebie day off work, so bookend a 3-day weekend with one or two days of PTO to create a mini-vacation in the middle of your trip. Sometimes, I like to travel on a three-day holiday weekend so I can dedicate the first day to getting to my destination, and still having two full days to settle in before having to login at work. 

Depending on the flexibility of your role and your relationship with your manager or your team, you could split up your PTO to take half days: Instead of taking 5 full days off in a row, spread them out over two weeks, working in the mornings and enjoying your locale in the afternoons. I’ve done this when things were too busy at work for me to feel comfortable disconnecting fully for a week. By taking half-days, I was able to stay on top of high-priority projects and still have a ton of time to wander and explore where we were staying. 

Let me give you a practical example of this in action. In 2018, we spent three weeks driving around the northeastern United States. We stopped in eastern TN, DC, Philly, New York, Plymouth, Boston, Salem, Kennebunkport, Portland, Vergennes, Montreal, Toronto, and Niagara Falls. We got to hang out with or stay with seven different friends whom we rarely get to see. 

We worked half-days every working day of the trip, which included a four day weekend for Memorial Day given to us by our company. We each took a total of 7 days of PTO, against an “unlimited” or “flexible” plan, that we spread out over the remaining 14 working days of the 23 day trip. 

We would never have been able to take a trip like that without working while traveling; by using the workcation approach, we were able to visit so many new places and spend time with so many awesome people in a short period of time. To this day, that trip is one of our favorites. (Read how I planned it here!)

Set boundaries and expectations with work.

Communicate clearly with your coworkers and/or clients about your availability and working hours while traveling. Even if you plan to work normal 9-5 hours, you should still establish boundaries

At home, you may find yourself working a little later on some evenings just because you can. But if you’re visiting a new place for a few weeks, you will likely want to log off right at the end of your work day to make the most of your time. 

Setting realistic expectations will prevent misunderstandings and allow you to enjoy your travel experiences without feeling constantly tied to work.

Find accommodations with strong WiFi.

Reliable internet access is (obviously) crucial for remote work. Don’t assume that everywhere you go will have a strong, stable connection. If you’re staying in a hotel, you shouldn’t have a problem but I would still call to ask. As we’ve been planning trips, we’ve been noticing an uptick in rental listings that show screenshots of a speedtest. So don’t hesitate to ask the host what the speeds are like and who the ISP is, and plan a backup! 

After a few days, Justin’s brother kindly printed out some motivational posters for our workspace.

When we stayed in Mexico, our apartment had decent internet…. Until the power outage that kicked off the week from hell. But I did not panic because I had already scoped out a local coworking space for this exact reason. I was also able to use my phone’s hotspot a few times when we had short outages. When we stayed in a home exchange in Chicago, my backup plan was going to the nearest Starbucks or public library. 

When selecting accommodations, prioritize places that offer strong WiFi connections. Read reviews, check internet speeds, or consider using a mobile hotspot as a backup option. This way, you can work seamlessly while enjoying your travels. 

Upgrade the cell plan, if necessary.

To ensure uninterrupted connectivity, consider upgrading your cell plan to include international data or roaming. A reliable mobile network can serve as a backup in case of WiFi issues or when you’re on the move. 

For example, we switched to Visible last year and selected their North America plan, giving us unlimited data, talk and text in the US, Mexico, and Canada. But the last time we traveled to Europe, we relied solely on Wifi, using WhatsApp for texting and voice/video calling. My father, who travels to Europe multiple times a year, subscribes to an international phone plan. 

Use my referral link to get $20 off your first month of Visible service!

Maintain a routine and schedule.

Traveling can throw you off. Whether you’re sleeping in a bed that’s too soft, eating rich flavors that your body isn’t used to, or visiting a country where you don’t really speak the language, it can be hard to feel “at home” and totally yourself while on the road. 

One thing I’m personally trying to get better about during long trips is setting a specific day to be laundry day. In Mexico, laundry took more time than at home because we did not have a dryer, so I had to allow extra time to hang the clothes and collect them later. I did at least one load a week to keep up.

Creating a routine while traveling helps create a sense of stability that will help you feel more at home. Set aside specific blocks of time for work, breaks, and exploring. If you stay in accommodations with a kitchen, you can add to that sense of normalcy by brewing coffee in the morning or cooking a quick pasta dinner to save some money for another adventure. 

Establish a regular bedtime and wake up time, just like you would at home. Give yourself a daily structure to help you manage your time efficiently, prevent burnout, and ensure you make the most of your travel experience.

Prioritize your sleep hygiene.

Traveling can disrupt sleep patterns, and we all know that a good night’s sleep is essential for maintaining focus and productivity. So prioritize sleep hygiene by creating a comfortable sleep environment and practicing relaxation techniques. Taking care of your sleep will positively impact your work and overall well-being.

Not the best sleep hygiene for our two-night stay at a friend’s condo in the Hancock building. Justin and I were sleeping on a blow up mattress and Skyler slept on the couch. Since it was only two nights, we knew it would be fine but this setup would not have been sustainable for the duration of our two-week trip! It’s very important to consider your sleeping environment when planning your travels!

I will admit I am still working on my own travel sleep hygiene. At home, I’ve got it down. I have my very firm Casper mattress, a sound machine that plays waves all night, blackout curtains and a facemask to prevent any light from disturbing me, a bluetooth headband to listen to a book as I call asleep, and  a fan to keep me cool. For travel, I take a sound machine and a facemask and my bluetooth headband. But I have been struggling with too-soft mattresses everywhere we go! If you have any tips for how to create a firmer sleeping situation while traveling, please let me know! My back will thank you. 

Embrace slow travel.

Instead of rushing from one destination to another, consider embracing slow travel. Spend extended periods in each location, allowing yourself time to truly immerse in the culture and explore at a relaxed pace. Slow travel fosters a healthier work-life balance and reduces stress, enabling you to enjoy both work and travel.

While we love a good fast-paced adventure full of attractions and sites to see, some of our favorite trips have been the slower ones where we’ve stayed in one place for a longer period of time. The places that I have fallen in love with, like the Hague and Paris and Playa del Carmen and Chicago, are all places that I’ve taken the time to get to know. Slow travel allows us to not feel rushed, to work full days without feeling like we’re losing valuable exploring time, and saves us money! 


My dad working during our 8-week family workcation to Whistler, British Columbia, way back in 2005.

Working remotely while traveling is an incredible opportunity to balance work and adventure, without falling behind or missing out.

I’ve been traveling while working remotely my entire life. Having been raised by work-from-home entrepreneurs, combining work with our travels was just how we did things. So it became how I did things when I started working. 

But even after nearly 20 (!) years of working remotely while traveling, I’m still learning and finding new things that make the experience easier or more enjoyable. So if you have a great tip or product or travel hack, please leave a comment below! We can all learn from one another and become better travelers.

By reframing your perception of travel, maintaining routines, prioritizing well-being, and setting boundaries, you can avoid burnout and make the most of your remote work experience. 

So pack your bags, set up your workstation, and plan a workcation! Get ready to embark on a journey that combines productivity and exploration like never before. Safe travels! Where are you going next?!

Disclaimer: Please note that this post is intended for those people whose work can be performed remotely, such as office-based or computer-centric professions. Always consider your job requirements, company policies, and any legal or contractual obligations before embarking on remote work while traveling. While the tips provided in this post can be helpful for many remote workers, it is important to ensure that your work arrangements align with your employer’s guidelines and expectations. 

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