How to Work While Traveling…From the Ground Up

Disclaimer: this post focuses on advice for those of us who spend most of our working lives tethered to a desk or a computer, in a traditional office working environment. For those of you who work differently, we salute you!

2020 marks a huge shift in office-based working environments and culture. We’re gaining new leverage, new confidence, and bargaining power when asking for flexibility. The great thing about working from home while traveling is that you can use work-from-home days to gain extra time with friends and family, while saving paid time off (PTO) days for international or destination travel. But before you speak with your boss or make travel plans with others, you’ll need to check a few things off your list and do your homework.

But first…plan

See our post on setting SMART travel goals to see what you want out of your year, and then figure out how many days off you really need, first. You’ll want to start conservative with your request if you do not regularly work from home. It does no good to ask for X# of days and get refused, when you actually needed fewer days. If you have the numbers behind what you need, it’s easier to be prepared for challenging communication. Since most of my family and friends live a flight away from me, I start travel planning with any known commitments: holidays, birthdays, weddings, catch-up with-friends travel, etc. I also plan transit days on either side of those trips, avoiding travel on a work day. I total the commitment vacations and see what I’m left with for the year, to see if I can work in any destination-travel. (Sometimes this exercise is performed backwards, if I have international travel planned). Here’s an example of what this could look like: 

Total PTO Days15
Out-of-state wedding: Fly Wed night, WFH Thursday, half-day on Friday for festivities, fly back Sunday-1.5
Out-of-state graduation: Fly on Thurs–work from airplane, WFH Friday, ceremony and return on weekend-1
Out-of-state Christmas with family: Fly on Sunday, WFH Mon-Wed, take Thu + Fri to help wrap presents and cook, return on weekend-2
Total remaining for international travel10.5
Without work-from-home days, you’d only have approximately 6 days left over for an international trip, which isn’t quite enough.

What I want to point out specifically is the work-from-home days when evenings can be spent with family and friends. Let’s say you had only planned to visit loved ones on weekends because you were short on vacation days. If you are able to secure a work-from-home arrangement, you can start your trip early, work remotely for a few days, spend bonus evenings with your loved ones, and still enjoy the planned weekend activity. Also, many people burn a week or more of vacation time for winter holidays when it may not be necessary. If you can manage family and friends around your work (e.g., say hello at breakfast and lunch), you could potentially spend time away on holidays without using vacation time.

Gather equipment and set up your tools

Make sure you have all the equipment and tools you need and practice with them before you travel. Equipment that I can’t live without: small retractable travel mouse; headphones; and stuff sacks for cables and adapters. If you need to work with your IT department to ready your system for working out of state, overseas, after hours, etc., start asking those questions well ahead of time. Be prepared to discuss your tech plan with your boss and open a line of communication with IT immediately. You may need a higher level of security and preparation than you expected.

Getting your tech in order also involves your personal technology. Be prepared for snags like internet outages that have you tethering from your phone’s hotspot. Make sure your phone’s data plan supports a new level of high usage, if only temporarily, and that this is a secure option for you. Consider the possibility that you may have to make a work-related phone call during international travel. Look into temporary international plans and sim cards. And don’t forget to pack the correct power outlet adapters for whatever country you will be visiting!

Write a proposal

Once you finalize your needs, write your proposal. Upper management may need to provide something to their upper management to justify the change. They need to know why they should let you work from home and how productive you’ll be. Don’t cite general statistics about how remote workers are largely more productive–use metrics unique to you. Track and time yourself on regular tasks and compare them to your in-office and at-home times. Collect average commute times (include time at home preparing for work). You may be able to leverage that commute time and turn it into the promise of an extended workday if that’s what it takes to reach an agreement. Also calculate how much you spend on gas, clothing, lunches, and happy hours. Your boss doesn’t necessarily need to know or care about how much it costs you to come into the office, but the numbers will help you understand what you need to ask for. Remember the last step about getting your equipment and tools in order? Include something in your proposal about how your technology is ready to go. Also take time zones into account. If your proposal includes travel outside your home time zone, consider adjusting your work hours to match your team if possible, and be very clear about what your working hours will be.

Get approval in writing

Is your office a strict or unspoken “butts-in-seats” environment? That’s ok. You can change the culture, at least for yourself; I’ve done it a few times. Nobody else works from home? Nothing about work-from-home in the HR policies or employee handbook? Exceptions can always be made and good things come to those who ask. Look up work-from-home policies and contract templates online, and “manage up” by drafting one yourself before you schedule an appointment with your boss. Have a few friends look it over for you beforehand. Make sure it’s easy to read and understand, and that you’re 1) not being unreasonable or 2) not advocating for yourself enough. 

Do your research

Working from the air

London from the air. A long-haul flight is the perfect place to get a head start on your work day.

I have found that I can work well in liminal spaces…in airports, on airplanes, in cars, in waiting rooms (as long as I have headphones). Knocking out half of your workday while on an airplane can save valuable PTO time. Research your airline and, if possible, even your departure terminal. Find out if wifi or power outlets are available on your flight, how long wifi will be available during your flight, and where the charging stations are in your terminal. I’ve been able to complete entire workdays even during the most hectic long transit days by stealing back my wait time. Every vacation day counts!

Working from “homes”

Working from your family’s or friend’s house is a great option to maximize vacation days. However, make sure you are clear with friends and family on when you will be working, what your hours will be, how and where you will be working, and how much free time you will have with them (this last one is quite important). I recommend that you plan at least one full weekend to spend quality time with loved ones aside from evenings. Also, don’t forget how to be a good guest. The real reason you’re there is to see your loved ones, not to work…that is secondary. Don’t wear out your welcome, make them hesitant to have you back if you’re working, or give remote workers a bad name. If your plan backfires or you feel like you’re not going to be able to spend enough time together, taking half-days is a good way to fix this. You can get up extra early, work your half-day, and be ready for quality time while your host is still making morning coffee. This is a happy medium between saving PTO and spending time together.

Discuss internet access with your hosts. Inquire about wifi, and upload/download speeds if you suspect you might need to share a high level of bandwidth (e.g., video calls). Ask about where you can set up. Is there a desk or a table that you can park at all day, mostly undisturbed? This is where having headphones or earplugs on hand is a lifesaver. If your hosts are home all day, everyone will be tempted to chat…even you. Hosts may not understand that working from home means actually working. Remote work can require more discipline than working in an office.

Have backup plans! If the wifi goes out or if there are other disruptions, you may need to escape to a coffee shop or library. Make sure you know how to access local business and services, transit, cash, food, and office needs (printing, etc.) in case you need to strike out on your own during the workday. 

Working from hotels

Research your hotel’s amenities prior to your trip. I’ve booked hotels with “wifi” only to find out that yes, wifi is available….for a steep hourly rate. Fun fact: Most hotel wifi is unsecured, and hotels are known to be hot spots for seedy internet activity. If you’re going to work from hotel wifi, make sure your device is well secured, and you’re using a VPN to connect back to the office. If you’re working with sensitive information, avoid hotel wifi. Other things to consider: available desks, business center, laundry, and food onsite or within walking distance. If you’re working during international travel, the location of your hotel becomes more important than you might think. I’ll cover this below.

Working from co-working spaces

My most remote working location so far has been from Dortmund, Germany. My husband had to travel there for work, and I wanted in on the action…especially during Weihnachtsmarkt season! While our hotel was a fine working location, it had no view, was surrounded by car dealers and industrial commerce, was isolated on the outskirts of town, onsite food options weren’t great, and there wasn’t anything within a quick walk. My biggest issue was that I wanted to feel like I was traveling. I was in Germany! I wanted to see the city and feel like I was a part of it. 

I did my research beforehand and landed on a very reasonably priced co-working space called Work Inn. I managed to reach someone who spoke excellent English (not hard in many European cities), and arranged to work in their common area for the week. If you’re not familiar with co-working spaces, they rent out office space in the form of private offices, conference rooms, and/or common areas. Individuals or small businesses can access temp work space, long-term occasional workspace, space by the day, or any other option you could think of. Coworking spaces are usually equipped with great wifi and office equipment, windows, lockers, water, coffee and tea, snacks, a receptionist, restrooms, A/V equipment, and other office creature comforts. My experience at Work Inn was fabulous. It was close to my train stop, had a great view, comfortable working options, and kind multilingual co-workers that let me crash their sushi takeout lunch! 

Know yourself

We hope our tips help you! But we also must warn you and acknowledge that working on vacation can defeat the purpose. It’s very easy to get burnt out, and not feel like you took a vacation at all. See our post: Remember that YOU Need a Vacation.

Have you ever worked remotely while traveling? Leave your tips and tricks in the comments!


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