Digital nomad: How to work and travel while beating deadlines from the road

Globetrotting and telecommuting present a few logistical challenges. These six tips will help you sate that wanderlust thirst and stay ahead of projects as you Zoom from the open road.

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Image: iStock/frantic00

Remote workers, no longer tethered to a physical location, can theoretically work from anywhere on terra firma. Globetrotting and telecommuting present a few technical and logistical challenges, but that shouldn't deter unbound telecommuters with a thirst for travel.

While the idea of working remotely on an extended vacation may seem like a daunting task, in the end, it's certainly a good problem to have. Threading the needle will require a bit of forethought, but the end result could pay dividends for adventurers.

Over the years, I've enjoyed several extended remote work road trips and hit my fair share of snags and technical snafus along the way. Below, I've listed six tips to help roaming digital nomads meet deadlines, finagle a remote hotel workstation in-situ and make the most out of that late checkout from the open road.

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How to work and travel: Digital nomad basics

Research the landscape

First and foremost, working from the road means pinpointing a home base for the daily telecommute and finding the ideal setup will require a little upfront research. A number of hotels are offering workcation deals specifically tailored for roaming business professionals with in-room workstations and even tech support included at times.

While regular Zoom meeting attendees will probably prefer the privacy of a dedicated room, people who rarely collaborate over video could readily work from the comfort of a coffee shop, balcony or even poolside if so inclined.

Before you book the trip, research the local hotels and see if any of the locations are offering special accommodations for remote workers. Also, remember to use resources like Yelp to see if you can access Wi-Fi at popular coffee shops.

Keep the team in the loop

It's also a solid idea to tell your boss, team members and business contacts about your upcoming workcation plans.  While this isn't mandatory in most cases it is good business etiquette. If something were to go wrong on the road, your boss is probably much more likely to give you a break if they know your situation rather than finding out you've been out of reach for hours because your rental car broke down in the middle of a trip to Tucson they didn't even know you were taking.

Living the nomad lifestyle doesn't mean looking like a fugitive in the eyes of your employer. Tell your boss and immediate team members your trip plans and keep them in the loop if things change.

Bring the office essentials

All right, once you've determined where you'd like to work, the next thing you'll need to figure out is how you'll go about your vacation workflow. Packing up the entire home office isn't exactly the most logical or even a feasible option depending on the setup; especially for people who are flying to their destination. For this reason, it's important to boil down the setup to the bare necessities without gutting the essentials.

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To help limit the luggage, try to determine the best way to use the assets on location. For those who prefer a dual-monitor array, consider running the proper cables to connect to the in-room TV, if possible.

There are also a number of travel-friendly options such as foldable keyboards, pint-sized portable displays and more to help professionals maximize duffel space without hefty baggage surcharges.

Additionally, you might want to plan for redundancy and bring backups (extra charging cables, blocks and batteries) in case of an emergency. Depending on the number of devices you plan to use, you may even need to bring an outlet multiplier or a ground converter for outlet interoperability.

Test the new office

So you've found the perfect room, double-checked your suitcase and you didn't forget a single thing? Don't pat yourself on the back too soon, you're not out of the woods just yet. It's critical to test the setup and take the new workstation on a dry run before the workweek begins.

Word to the wise: Do not plug in the laptop 30 minutes before the Monday morning scrum expecting everything to go without a hitch. If you do, you'll have only yourself to blame if and when something goes awry.

Sign in and test the Zoom room before the live event and check the Wi-Fi performance in advance. There are innumerable Wi-Fi apps on the market and plenty of free options available to help you test connectivity on location whether the "office" is in the executive suite or on a rooftop patio.

Setting aside a few minutes to test the setup will help ensure a smooth start to your trip. Odds are, you'll thank yourself later. 

Be a professional

When traveling and working from the road remember to keep professional priorities in focus. Simply put, if you're not taking time off, you're not on vacation. Working from a destination is not an excuse to go wild, drop offline early and stay out late at the expense of your own productivity. Enjoy yourself, pick your spots and maybe take a half-day here and there to maximize the weekend. The ability to work remotely and travel concurrently is a great perk to have. Like anything else, if a person misuses this leeway, they could risk losing the benefit in the long run.

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Carve out time for adventure

Most importantly, be sure to carve out some time to enjoy the ride. While working and traveling at the same time will require a little more due diligence—and at times self-restraint—maintaining a healthy work routine in the middle of a great adventure is more than doable.

Remember, you don't know if you'll ever be back in a particular city, so set aside time to see the town and make the most of the opportunity. For some, this could mean making a physical list of sights and seeking out one item each day. For others, this could simply mean going for a walk in a different neighborhood each night.

What does the city sound like on a Saturday night? What's the local dish you couldn't get enough of? Where's the best spot for people-watching? While the Sherman deal or that well-executed PowerPoint presentation certainly pays the bills, the look and feel of a destination will be the things you'll remember in hindsight.

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