Traveling While Working Remotely: 10 Expert Tips to Best Balance Both!
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One undeniable perk of being able to work remotely is the ability…to well…work from ANYWHERE. Well, anywhere with internet access that is. Whether you want to be a long term digital nomad, living in countries for months at a time (or until your visa runs out!), or if you’d rather just add on a day or two to your vacation, having the option to work remotely opens up a lot of potential possibilities to travel. Like…you can literally be traveling WHILE WORKING remotely.
However.
Like a politician, working remotely promises a lot of perks, but how do you actually balance it all without your job performance suffering or putting a damper on your vacation? Is it really worth the money to be cooped up in a hotel room filling out reports when you could do that at home for free? Where do you find reliable wifi when traveling? Especially abroad?? And more importantly – how do you get started???
Don’t worry, that’s what I’m here for! Since I do NOT have a job capable of going remote (I work in manufacturing, womp womp), I have a lot of questions about traveling while working remotely. Luckily, some of my good friends DO work full-time at a remote capable position, and they use it to its full potential and squeeze out as much travel as possible. Today, I’m sharing all of their best tricks of the remote trade to help you have a smooth experience as you venture into combining work and play!
So enough ado, let’s meet the traveling while working remotely experts themselves!
Table of Contents
Panel of Experts!
We’ll start by asking our four panelists a bit about themselves, their job, and how their work became remote! You’ll probably find that one or more of the following panelists has a similar work environment or field as you, and if you are not currently remote, you may be able to apply some of their job’s reasonings to push your own position to be more flexible.
Sojourner from Sojournies
Homebase: USA
“What do you do for work?”
Sojourner: I am a Project Management Strategist at UBUNTU Research and Evaluation, where I do strategic planning, research, and evaluation consulting. We are a strategic learning organization powered by unapologetic Black women, femmes, and nonbinary people working as transdisciplinary strategists committed to resisting anti-Blackness and building the intellectual and political defenses of all Black people, in solidarity with the global majority, through education, facilitation, and evaluation.
Alexandra from Alexandra Kidd Travels
Homebase: UK
“What do you do for work?”
Alexandra: I am an Online ESL Teacher (English as a second language). My classes range from teaching English to both adults and children.
Erin from Pina Travels
Homebase: Canada
“What do you do for work?”
Erin: I am a Full-time Content Marketing Specialist. I develop a content strategy and write blogs, ebooks, guides, whitepapers, and other content for an adtech company that’s based in Toronto, Canada.
Nora from Go Frame The World
Homebase: UK
“What do you do for work?”
Nora: I am a Software Architect, and my day-to-day includes aiding customers and designing and implementing software at my company.
Is Traveling While Working Remotely only a “English-speaking/western country” thing?
You might have peeped it, but all of our panelists are from English-speaking western countries. And while their range of professional skills are varied, they do all speak English and are residents of western countries.
So what does that mean for…everyone else?? Can people from other countries and language backgrounds still experience traveling while working remotely? Absolutely! And if you fall under that category (or even if you don’t), my friend Andrea from It’s a Travel OD has incredible resources and services that can help you find and GET remote jobs (or remote capable jobs!). Reppin’ her home country of Panama everywhere she goes, Andrea especially emphasizes remote work opportunities open for residents of non-English-speaking countries. She has helped people from every corner of the globe, so I’d highly recommend checking her out!
Alright, now that you’re all set up and you’ve met the panelists, let’s find out how to best prepare for traveling while working remotely!
And yanno, enjoy the random stock image models throughout this piece, haha.
Has your position always been remote capable?
Sojourner: No! I got hired during the pandemic in June 2020, and technically it wasn’t remote until then. Our work used to be heavy on in-person facilitation workshops with education institutions. However, the pandemic decimated a lot of that work and we had to pivot. Now, UBUNTU is heavy on the evaluation side.
We primarily do qualitative evaluation through focus groups, individual interviews, etc. which can easily be done virtually (though outreach and coordination can be difficult at times). I also do a lot of the strategic planning which often includes focus groups, individual interviews, other online facilitation, and possibly one in-person workshop depending on the organization.
We went permanently remote earlier this year, with team retreats in person (at least twice per year). And aside from standing meetings, most of my job is asynchronous (meaning we work at hours that best suit our productivity levels) as well.
TIP: If your job wasn’t technicallyyy remote before, maybe it’s time to revisit being remote for the long term!
Erin: My company was always pretty lenient about working remotely. We were expected to be in the office most days, but if you wanted to work remotely while spending a week with family, for example, that was generally fine. But, the pandemic totally changed this! My company now calls itself “remote-first.”
They now hire all over Canada and the US, and all employees are welcome to work from anywhere within their own country. And actually, in some cases, they are allowing people to work from abroad, as long as it’s for a defined amount of time and not a permanent move. There’s no plan to re-open the office in Toronto, so I consider myself a permanent remote worker now!
Nora: Yes and no for me. While nothing I do necessarily requires me to be onsite, I have always spent a few days a week at the offices of my customers wherever they were in Europe. And it’s not that we don’t have the technology to execute our tasks efficiently remotely. The reason was that face-to-face interaction has always been easier and allows you to build a relationship with the people you work with.
But since the pandemic hit, many companies realized that allowing people to work remotely does not affect their performance negatively and is actually cheaper. So I’ve been working fully remote for over a year and a half now, and even when travel goes back to normal, I will keep working remotely most of the time.
TIP: Or…just get a job that is inherently remote!
Alexandra: I always knew that the Monday to Friday daily commute wasn’t for me. During the pandemic, I decided to do something about it and took a CELTA course which would allow me to teach English online, as well as anywhere in the world. In May 2021, I quit my full-time job, gave up my flat in London, and have been teaching online since.
How much vacation time do you get at your job?
Alexandra: I am self-employed so I can take as much vacation time as I want, I just don’t get paid for it.
Nora: I get 26 days a year. Not enough really. Working remotely has allowed me to at least travel and see different parts of the world on weekends, mornings, evenings. Sometimes I have a very flexible work schedule and that allows a lot of freedom to explore and work whenever it is more convenient.
Sojourner: We have 5 mandatory vacation weeks (3 weeks during holiday time in December/January, 1 week during the week of Thanksgiving, and 1 week for a summer or spring break); there are also other mandatory time-off holidays sprinkled in there too. We have also unlimited PTO (paid time off), which I normally plan around my projects to make sure I can maintain a good workflow with the rest of the team.
Erin: The tech sector is known for being way more generous when it comes to vacation time than other sectors, it’s part of why I decided to go this route with my career.
In Canada, the basic entitlement is 2 weeks of vacation for every completed “year of employment.” Before I worked in tech, I only had 2 weeks of vacation, and I found it really hard. I am so privileged to have my current job, which gives all employees 6 weeks of paid vacation per year, as well as a couple of personal days, and unlimited sick time.
In many companies in Canada, you “earn” more vacation the longer you stay with a company. Mine doesn’t do that – everyone, no matter how long they’ve been at the company, has the same vacation time, which I think is way more fair and promotes better work-life balance. Traveling while working remotely definitely helps me stretch this time! For example, I recently did a trip to Eastern Canada, and I did a mix of working and taking vacation days, which helped me stretch out how long I spent there.
How does your job feel about traveling while working remotely?
Nora: I am lucky to be working for a company that supports traveling while working remotely, and even short-term relocations.
Erin: They don’t really care where I am or what I am doing, as long I am within Canada, and online when I’m meant to be. And on top of my deliverables of course. If I’m leaving the country, traveling while working remotely is fine for a few days or weeks, but if it’s for a longer period my company might not approve of it because it can impact their insurance.
Sojourner: My job actually knows about my Sojournies work so they already knew it would be a thing I would do. They are very supportive. We all love to travel in some capacity, so it’s both an organizational and individual priority.
Do you disclose when you are traveling while working remotely?
Alexandra: My students like to hear stories about my travels and always ask where I am. I never share too much personal information with them, but will share some details of my travels.
Sojourner: Yeah I do! We are consultants, but our work is very collaborative. Though, I haven’t gone abroad while working remotely at this job. Yet.
Erin: I think this is a bit of a personal choice. My partner, for example, doesn’t usually disclose where he is. There isn’t really any reason that his boss would need to know, anyways. I have a great relationship with my manager, and when we have meetings I usually have my camera on, so I typically will tell her…she would notice that my background has changed, haha! But I don’t bother telling the rest of my team.
Nora: It depends on how long I intend to stay away from my home country. For short periods of time, there is no need to notify anyone. If there is a difference in the time zone I usually notify the people I work with directly at that time.
How do you make traveling while working remotely productive?
Nora: I’d say fast and reliable internet connection is the one thing I can’t do without. If I’m being picky, I’d also say I need a comfortable space to use as a “home” office.
Alexandra: I always use a VPN for cyber protection when using hotel wifi and other public internet connection. My partner and I travel together, so we have to think about whether the space is suitable for me to teach, while he is also using the space. We spend most of our time in studio apartments or hotel rooms, and so far have managed this successfully. If I have early classes I will use the hotel bar to avoid waking him up!
When I am able to plan in advance, I can alter my teaching schedule to allow for time spent traveling, day trips, evening meals etc.
Erin: When I’m working from my home I have a ~ fancier ~ work setup, but when I’m traveling while working remotely, I keep it pretty basic. Sometimes I will also bring my laptop riser and a mouse. I also always stick to my regular work hours while traveling. I usually work 9-5, so I keep up that routine regardless of where I am. This is important because it helps me keep in sync with the rest of my team at work.
Sojourner: In a post-pandemic world, whenever that will be, I will play around with coworking spaces and cafes more, but I haven’t done much of that due to COVID. In addition, what has been helpful for me organization-wise has been to schedule time for calls and block out when I’m unavailable externally/internally to the team.
Especially since we’re remote and asynchronous, I don’t want to leave a co-worker hanging. It’s happened before by accident and it can really have a negative effect on a co-worker relationship. So I notify my project partners when I’ll be out-out vs working elsewhere, and update my Slack and Google calendar status so people who may spontaneously need me the day of also know where I’m at.
What are the challenges of traveling while working remotely?
Erin: It’s funny because I always romanticized working remotely.
For years, it was my goal to get myself into a career path that would allow working from home and from other locations. In reality there are definite challenges to it. Travel is unpredictable sometimes, and that can make sticking to your work routine stressful.
I have found that when I am traveling while working remotely, I can’t focus quite as well on my work as I do when I work from my home. Part of it is that I’m just so excited to be in a new place haha, but it’s also because I’m a creature of habit. I get distracted easily, especially if I’m in a new space. That said, I think over time my ability to focus when I’m traveling while working remotely is improving – it might just be that I need more practice!
Another challenge I’ve faced is WiFi. While on Prince Edward Island earlier this year, my partner and I checked into a cottage that had advertised good WiFi…which in actuality barely worked. Our jobs are corporate, and while they are okay with traveling while working remotely, it’s a bad look to say one morning, oh sorry I’m vacationing on the coast of Prince Edward Island, and the WiFi is bad, oops!
So, we spent the first few hours of our work day frantically driving to the nearest little town, looking for a cafe with good WiFi that would allow us to hang out while working. Finally we found a cafe, but it was difficult to manage working from it, because it was busy and had loud music and people chatting.
My partner was having a tough time keeping up with his meetings. In the end, we had to drive even further and book a room in a random hotel that we could work from. Lesson learned! From here on out, we will be emailing accommodations to triple check that the WiFi is fast and reliable before booking.
TIP: Triple check the WiFi AND give yourself enough time before your work day to find other arrangements if needed
Alexandra: I am not able to be flexible or spontaneous with travel plans if I have classes scheduled, and I won’t cancel lessons unless I have no alternative. This means that I have to plan in advance, or can only travel on my scheduled days off.
For example, we recently spent two weeks travelling around The Netherlands, changing location every 2-3 days. We had to plan the moves around the lessons already scheduled, ensuring we could check into the next hotel before my next class. Most hotels/Airbnb’s have check-out at midday (11am in The Netherlands as we found), and check in from 2-3 pm, this meant I needed to do a bit of forward planning to make sure that I had somewhere suitable to teach.
TIP: You may have to fall back on your mobile services if you are unable to have reliably WiFi. Be sure your backup is in place with a mobile hotspot (like Keepgo!) or pick up a local SIM card with unlimited data.
Sojourner: I would say my job’s main concerns are (1) the workflow of our projects – because being a consultant is a balancing act and (2) time zones.
Since we have a lot of internal team meetings, focus groups, client check-ins, etc, I have to be conscious of where I am so that I don’t have a bunch of meetings at odd hours like 9pm to 6am or something. As I look toward traveling while working abroad one day, I’m looking specifically at the Western Hemisphere. It has the perk of close time zones, plus I haven’t done a lot of traveling in that area.
Also, scheduling flights is a pain sometimes. I try to catch flights that are outside of work hours (either really early or after 5pm) so I can get what I need to get done and relax on my flight. Sometimes it works…and sometimes it doesn’t and I’m doing work in an airport – normally typing on a Google or Word doc and not taking a meeting.
Nora: Personally, I find that traveling while working remotely leads me to unconsciously stretch my working hours. I have to keep reminding myself that unless there is something that must be done the same day, I should stick to a strict work schedule and not overwork myself, which is easier than it sounds when you’re on a different time zone as everyone else.
Although, it is also an inconvenience to carry around a very heavy laptop or travel essentials for remote workers, so if it’s a short trip, it might be worth a few extra hours beforehand to be able to coast during your trip.
Do you feel like working remotely while traveling changes your travel experience?
Sojourner: Oh definitely. I think I’m more conscious of when I fly and what makes the most sense for my work schedule. I do work on the plane more if I need some extra work time or don’t wanna do it when I land. I even learned to pack a bit lighter so I have less stuff to worry about.
If I’m traveling with co-workers we also talk about work more while waiting in the airport, etc. but it’s more relaxed. I wouldn’t do that if I weren’t traveling for work. I also thing I appreciate the destination more because I’m not just sightseeing all day, I’m working. So I love getting fresh air, finding cool happy hours, etc. In a lot of ways it makes me more of a slow traveler.
Nora: Traveling while working remotely a different type of travel entirely. I don’t have the feeling I am on vacation. It feels more like I’ve relocated somewhere I haven’t been before. And the experience is a lot different because I don’t rush things into a tight schedule, but rather take the time to visit places and do various activities whenever it’s possible. One weekend at a time, a few hours during the week. It’s actually a lot more relaxed because it’s not limited to the PTO I have left.
Alexandra: Yes, but mostly for the better for me. When I am on holiday I tend to spend as much time relaxing as exploring. Now, any time when I am not working is spent outside getting to know my new environment, so I feel much more productive (travel wise) and that I am making the most of my time.
Of course, there are days when I would rather be sunbathing than working, but during my summer trip to Gaucin in Spain, I was able to jump in the pool for a swim between lessons. I definitely couldn’t have done that from the office in London.
Erin: Yes, traveling while working remotely completely changes the experience. My job isn’t super stressful, but it does take up headspace. And so the biggest thing for me is that traveling while working remotely doesn’t feel as relaxing as traveling on PTO does.
All your daily work responsibilities follow you, which means you don’t get to “vacation” in the same way that you do if you’re actually on vacation. The other thing is, you have less time to enjoy the place you’re visiting, because your daytime hours are taken up. What we’ve learned is that slow travel is especially important when traveling while working remotely.
We have always been slow travelers in the sense that we like spending a good chunk of time in a place before moving on, but while working remotely, we are spending even longer. You have to stay a while if you want to actually get to know a place while balancing work!
What have been your most exciting trips you went on while working remotely?
Nora: My last few trips were away from the cities, and that has all been pretty exciting. It’s great to be able to get up in the morning, sit in front of the hut with a cup of coffee, and enjoy the silence of the mountains while going through emails. Or having the beach as your office space, that always feels fantastic as well.
TIP: It may take a little extra checks, but traveling while working remotely is possible in nature-focused trips as well!
Alexandra: I loved the freedom of being able to explore The Netherlands while knowing that I was able to work and make money to fund the trip. The best thing is knowing that we didn’t have to rush back to the office for Monday morning. We’re currently making plans for the ski season and that will be very exciting. The only thing restricting us is how long we are allowed to remain in Europe!
Erin: The east coast of Canada, probably because it’s our most recent remote working trip! This past October, my partner and I traveled around Nova Scotia, from Halifax to the Bay of Fundy, Lunenburg, and up to Cape Breton. We also spent some time on Prince Edward Island. This was our first “big” trip since the start of the pandemic, including our first time on a plane!!!
Because we haven’t traveled far from home since the pandemic began, this trip was especially exciting for us. The east coast of Canada has so much soul, we fell totally in love. One of my favorite parts was driving the Cabot Trail in Cape Breton. It’s one of the most scenic drives in the world!
Sojourner: We had a team remote opportunity to go to Nebraska for a week for a project. I had never been to the state and it pleasantly surprised me. I also took a 52-hour train ride from Chicago to California, and while I didn’t work on the train because there is no wi-fi, I did a bit of work in San Francisco. I also worked remotely in South Carolina after a weekend trip there, and I’ll be working remotely from Pittsburgh later this month for a few days.
I’ll be doing more long-term remote work next year, and most likely gonna spend some time on the east coast of the U.S and then Mexico in summer/fall 2022.
What advice would you give someone that is hesitant to travel while working remote?
Erin: Start small! Ease yourself into it by experimenting with shorter remote work trips that don’t take you too far from home.
My partner and I started by booking cottages near where we live, just for 2-5 day stretches. That helped us get into the groove of remote work, and was a good way for us to figure out what our personal “essentials” are for working while away from home. And, don’t worry if you realize that remote work isn’t for you. It definitely comes with challenges, especially if you have a demanding job. While I love having the perk of working remotely available to me, I think I still prefer traveling while on unpaid leave or PTO!
Alexandra: I would recommend making things as simple as possible. Only pack what you need. I no longer stress about packing, as I know it will only take me 10 minutes to fill my backpack in the morning before we check out. Trust me, you don’t need as much stuff as you think you do, but it might take a few trial and errors to get it perfect. Spend some time thinking about how you can arrange your schedule to make the most of your free time. I work alternative mornings and evenings which means I have suitable time slots for students in different time zones, and also have 24 hours between lessons every other day.
Nora: If you have the possibility, then definitely give it a shot. And if you give it a shot, then take your time traveling while working remotely. The travel experience is much different when you’re visiting a place as a tourist, compared to when you’re actually living there, albeit temporarily.
Sojourner: I would say don’t knock it til you try it! It’s one of the biggest perks of remote life, so why not? Just have clear communication and boundaries with your employer.
Traveling while Working Remotely: Conclusion
And there you have it – the comprehensive list of tips, tricks, and sage advice on how to balance traveling while working remotely…without getting fired. Remember, even if you don’t end up not liking traveling while working remotely, at least you took advantage of the opportunity and experienced it for yourself.
If you’ve tried out traveling while working remotely, share your tidbits of knowledge in the comments below! And if you haven’t – ask any additional questions or concerns! We’re here to help!
Again, I want to thank all the wonderful panelists for sharing their insight on traveling while working remotely. Below are all of their social channels – please give them a follow for more tips!
Nora from Go Frame The World
Erin from Pina Travels
Alexandra from Alexandra Kidd Travels
Sojourner from Sojournies
And again – if you’re on the hunt for a a job where you can try your hand at traveling while working remotely, hit up my girl Andrea at It’s a Travel OD. She’ll get your resume looking RIGHT for those remote hiring managers! I also have resources for balancing traveling as a full time student AND traveling in grad school, so be sure to check those out as well if you’re in school.
Now that I mention it…yanno…there is a specific engineering position at my workplace that would allow me a little more flexibility with remote work…this post has me eyeing that job rec….
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