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The must-know tips for traveling while working

Laptop at rooftop bar

When I first started working remotely, I thought traveling while working would feel like having unlimited vacation time. The ability to be wherever I wanted as long as I got my work done opened up locales and itineraries that I never could have dreamed of with the number of days off I got per year. I worked from a hop on, hop off bus in Barcelona, a boat cruise in Stockholm, and a car parked outside a waterfall in Iceland. I’m pretty sure my work-from-home tally now tops 16 countries and 30 U.S. states.

As I came to realize, though, traveling while working is a whole different ballgame than simply taking a trip. Your pace, priorities and packing list are all different when you’ve got your job to think about, and navigating the balance between work and travel can be tougher than you’d expect. Below, I’ve compiled some of the tips that have helped me along what’s been a multi-year learning experience, in case they’re helpful for you as well!

THE MUST-KNOW TIPS FOR TRAVELING WHILE WORKING

ALWAYS HAVE A WI-FI BACKUP PLAN. ALWAYS.

For most of us, one of the top two most important things we need to do our jobs is a Wi-Fi connection, and I can’t stress enough how important it is not to take good connectivity for granted. Relying on Wi-Fi either working or existing at all at a certain locale has burned me countless times, and now I never go anywhere without a backup plan. 

For starters, Wi-Fi on airplanes is not reliable—period. If I have to fly during my actual working hours, I will take the day off, and then, if it turns out I’m able to get online, un-take it off! If the flight is outside of working hours but I still plan to get things done, I’ll screen shot all the info I could possibly need for writing or plan an offline activity such as photo editing.

Skyroam Solis

SKYROAM

For on-the-ground travel, I’m not sure how I got by before Skyroam, a pocket Wi-Fi device that works in more than 130 countries. I have a plan that includes 1GB of data per month, which most months is much more than I need. But if I’m abroad and wanting to keep it on more often, I can buy an additional 1GB at any time for $9. It’s super affordable, and if you travel for your job in addition to in spite of your job, your company may even consider it a reimbursable expense!

Of course, Skyroam isn’t foolproof. It relies on 4G LTE, so if you’re in a remote place with no service, it’s probably not going to work. The device itself can be quirky, too. If I really need to be online, I’ll make sure to be somewhere with its own Wi-Fi network, but Skyroam is a great option for if that connection is spotty or not working. Outside of working hours, it’s great to know that no matter where I’m traveling, I can still be reachable by Slack or whatever my team is using to message me (not to mention the fact that it’s helpful for non-work traveling, too!)

OTHER OPTIONS

There are other options beyond Skyroam, of course. If you have an international data plan and can hotspot your computer, I’m jealous! But absent that, I like that with Skyroam I don’t have to find a place to purchase a local SIM card for my phone and that Skyroam enables me to connect multiple devices at once.

No matter what you use, point stands—if you’re going to be mobile while on the clock, you need to make sure you have the tools to do the job. (This applies to domestic travel, too, by the way—I use Skyroam all the time in the U.S. if I have to go to a doctor’s appointment or get into an Uber and want to work on the go.)

Converter

ALWAYS HAVE A POWER BACKUP PLAN. ALWAYS.

Wi-Fi is obviously critical, but it won’t do you much good if your devices are dead. Which brings me to the second most important component of successfully working while traveling: Power.

For every Wi-Fi nightmare story I have, I have another one involving my computer charger breaking in Indonesia or realizing from a remote Italian villa that the converter I have won’t plug into the outlet. 

IN MY BAG

As a result, I’ve become somewhat of a cord-hoarder (as Jake says, “it’s better to have it and not need it than need it and not have it”). At baseline, to ensure I’m able to communicate, I have a phone charger on me at all times no matter where I am in the world, as well as a USB-C converter so that I can draw power from my laptop if I can’t find an outlet. When I think of it, I also toss the mophie power bank into my bag just in case. 

If I’m abroad, the Skyroam comes along too (it can function as a power bank in a pinch), and so does its power cord; I mentioned the device could be finicky, and I find it works better when it’s fully charged. I also always carry a small converter that works with local outlets and will easily fit into my purse. Then at home, I have a larger power strip with multiple outlets so I can charge my computer, phone, Skyroam, camera batteries and more overnight. I use this one, but warning that it does buzz lightly when it’s on, so if white noise bothers you, look elsewhere!

Is it a lot? Yes. But at least for me, the flexibility I have at work is a direct result of having shown that I’m responsible and can get done what I need to do—no matter what.

One more note: Apple cords in particular are extremely fragile and if tightly wound will easily break. Learn how to store them in a way that doesn’t put too much stress on the parts that have to bend, either by wrapping them loosely or buying a dedicated container for optimal storage. An Apple Store employee showed me how to do it!

Bondi Beach

DOUBLE YOUR TRIP LENGTH

Here’s a mistake I’ve made far, far, far too many times: Planning to work remotely while only having one or two days in a city. I somehow always forget to adjust my itinerary to account for the fact that I won’t be exploring non-stop, and I spend my time ultra-stressed out that I don’t have enough time for sightseeing, my work, or both. Plus, I leave feeling like I missed out and just need to come back, which makes me feel like I wasted my resources planning a too-short trip in the first place. Overall, not good!!

These days, when I can, I aim to double the amount of time I’d otherwise spend in a specific location if I’m bringing work along. That strategy gives me the breathing room to make sure I get everything done, even if additional work comes up that I didn’t anticipate. 

When traveling while working internationally, I like to pick out one big city (such as Buenos Aires, Sydney or Tokyo) and just stay there for an entire week. That way, in addition to avoiding the stress of FOMO, I also avoid the stress of moving around (and, more importantly, the transit doesn’t impact my ability to do my job).

SET A SCHEDULE

People ask me all the time how I stay disciplined enough to get work done while I’m exploring a city abroad, and the truth is that I have no choice. I operate under extremely strict deadlines at work, and my morning hours are non-negotiable. For instance, If I didn’t have that set structure in place, I don’t know that traveling while working would even be feasible for me since I’m not the best at managing my time or saying no to things I want to do!

If you’re in a similar boat but don’t already have a schedule you have to abide by, set one yourself. If you stick to it, it’ll ensure you’re devoting enough time to your work obligations, and for so many of us, doing that is critical to having the freedom to work remotely in the first place!

Charter Hotel Seattle desk

HOTELS OVER AIRBNBS

I know this can be a hot take, but I vastly prefer hotels over Airbnbs all the time—especially, though, when I’m traveling while working. Just yesterday, I moved from a hotel to an Airbnb in Prague, and nearly the first words out of my host’s mouth were, “sometimes we have issues with the Wi-Fi.” Sure enough, the second he left, I couldn’t find the network, and the password he gave me for the backup network wasn’t working.

Luckily, I had my Skyroam to get me through until I figured out how to fix the issue (I’m telling you, backup Wi-Fi for the win), but I don’t go on a trip to spend my time troubleshooting connectivity issues. I love the fact that at a hotel, you have people who can take care of those types of problems to minimize disruptions.

Wi-Fi aside, I also just find everything to be easier at hotels, where you often have a concierge to help you answer questions and navigate foreign-language situations, as well as the option to procure food or drinks without leaving your workspace. Plus, my time is usually stretched thin enough when traveling while working that I want everything logistical to be as quick and simple as possible. 

Of course, hotels can be pricey, especially when you’re looking at doubling the length of your trip! And that is, of course, where points come in. To learn about how points and miles can help you snag hotel stays for free, visit the 52 Cities free resource library or join a points and miles masterclass! 

Hope these tips helped you plan for traveling while working! Do you have any other questions about working remotely? Leave them in the comments! >>

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