A guide to mastering the art of digital nomadism

May 15, 2023

For the past five years, I’ve become used to a lifestyle that blurs the lines between work and travel. I live abroad. I freelance. And I’ve worked from home since before the pandemic made that normal. Normally, I work from my apartment but because I travel often (locally and domestically, but also to neighbouring countries and of course, my home in Canada), my laptop is often in my carry-on and I’m frequently working from hostels. This may not be a typical digital nomad lifestyle but I’ve certainly done my fair share of nomading with laptop and chargers at the ready to write and edit from wherever I happen to be.

I’ve worked in some pretty obscure places—the backseat of a minivan winding its way through the mountains, a valley where a local farmer tended to her sheep, hostels, airport gates, night buses, stranger’s kitchens, and the picnic table of a provincial park, to name a few. It’s not the norm by any stretch (no duh, right!? Imagine the unsustainability…) That said, getting familiar with the digital nomad lifestyle is something that enables you to get more from your vacation time.

And, I want to acknowledge the flexibility that working for myself offers. Not everyone can do that and I get that other roles don’t necessarily enable workers to submit their work from a hiker’s lodge. Speaking specifically to those who can work remotely—be it for a couple of extra days after a long weekend or for months of the year—this is a lifestyle that can bring immense value… when done right.

So for those who live in (or travel to) Canada, these below tips will also help you get more mileage out of the summertime because you can extend your time in fun places like Jasper, Vancouver Island, Banff, or P.E.I. by bringing the office to you. (If your employer allows it, that is.) But a word of caution: mixing work and travel isn’t all sunshine and rainbows… this is going to take more planning and self-discipline than you may think!

Set your schedule in advance

If you're looking to make the most of your travels while still maintaining a somewhat normal workflow, then you’re probably going to want to do some planning ahead. Decide on what your working hours will be before your trip starts. I know this type of trip planning isn’t exactly thrilling but trust me, you’re doing yourself a favour.

I’ve learned this the hard way. I’ve been in a situation where I’ve intended to sit down and chip away at research notes. But the day can easily take over when beach walks or a group dinner look more enticing than your blank Google document. Without structure, it's easy to fall into a cycle of procrastination or become consumed by work and miss out on exploration and adventure. By planning your work hours in advance, you can stay on track, get your sh*t done, and then go off to chase waterfalls, or rollerblade around Vancouver parks, or track down Quebec City’s best cocktail. Or whatever it is that you do.

Digital Nomad 1

Travel with like-minded people

I’m fortunate that my friends *get it.* My besties are digital nomads too. They’re tied to meetings, differing time zones, teaching schedules, and deadlines. So when we go for a little girls getaway and extend the weekend here and there, work always comes up in conversation. We hold each other accountable and we keep each other company in our “office.” Oftentimes, evenings consist of mutual planning. As in, “I’m going to skip out on drinks and so is X. We’re both going to work tomorrow.” Or, “Let’s agree to work 9-1 tomorrow and then hit the beach!” When you have someone in the same boat as you, it’s just easier. Plus, less FOMO!

When you link up with other “digital nomad” types (you’ll bump into them in hostels for sure!), there’s also the added benefit of connecting with like-minded people, sharing experiences and ideas, and bouncing ideas off of one another. Once, on an island off the coast of Colombia, two former classmates and I exchanged drafts. It was like having beach-going friends and personal editors all in one!

Communicate expectations

What needs to get done while you’re off on your Rocky Mountain or quaint coastal adventure? What’s a priority and what’s going to wait until your return? As a laptop-toting traveller, it's a pretty good move to communicate your expectations with clients or employers before you hit the road. Set clear expectations about what work needs to be done while away, and be in agreement about which projects can be put on hold for now. And set that out-of-office responder for those who wouldn’t necessarily be aware.

For clients I’ve had closer relationships with, I’ve been known to call or text before leaving a wifi zone while we’re working on an ongoing project. That has sounded like, “Hey, you should have received the web copy. I’m at my gate and won’t be able to respond to edits until tomorrow.” Or, “The pages you asked for are done. I’ll be on a boat so for any comments you have or edits you need, I won’t see them until Tuesday.”

By establishing these expectations upfront, you avoid misunderstandings and ensure that everyone is on the same page. That means you can properly relax and be in the moment without work weighing on you or bringing anxiety to summer evenings meant for stargazing and bonfire chillin’!

Make sure your accommodation has proper wifi and workspace

And even check a second or third time. Seriously. If you’re someone who works remotely in order to maximize your travel time, you might know the struggle of trying to get work done while battling unreliable Wi-Fi and a cramped or noisy workspace. Hostel hack: call them in advance. Email the manager to double-check. That legwork will cut out so much stress, I tell you! I’ve completely found this out the hard way. It resulted in a missed deadline and I wasn’t able to enjoy my trip because I couldn’t stop thinking (stressing!) about it. Ugh. That was a hard one.

Trust me, the last thing you want is to spend your entire trip hunting for a decent signal. Stay in a place where you feel confident that your work needs will be met. Then just get it done and you’ll be free to do summer activities like photograph wildlife or cycle along the Icefield Parkway.

Coworkhostel

Keep the itinerary realistic

I think this is the hardest area of the work-travel lifestyle to manage. Some of us—particularly, erm, creatives—have a wildly unrealistic notion of what can all fit into a day. Guilty. As. Charged. I’ve been known to wake up at 5:00 a.m., write a blog post, hike a mountain, go for food and drinks afterwards, and absolutely burn out. I’ve also been known to seriously, honestly believe that I can leave town for the day, spend a full day exploring in the sun, and return with enough brain power to draft a full essay at night when everyone else is asleep. That’s… dumb. Don’t be me. Rein it in my friend. For your sake, please.

It's important to be realistic about your travel itinerary so that you can find balance and not set yourself up for failure. It's not just about hitting the top tourist attractions or checking everything off your list. You also need to factor in daily responsibilities or time zone differences. Unlike regular backpackers who might have their days free, digital nomads need to consider a daily work to-do list while on the move. And that can be a really rewarding thing! Take a look at your day and ask yourself: Is that honestly doable? While it can be tempting to try to squeeze in sightseeing and other activities, it's important to simplify your itinerary so as not to compromise both your travel experience and the quality of work you get done.

Do hard work in advance

I mean, this is pretty self-explanatory, right? Keeping on top of work while travelling can be challenging. Expectation: Laptop at the beach. Reality: setting the alarm two hours earlier than your friends so you don’t have to take the stupid laptop to the beach. The sand! The keys! You can’t even see the screen with the damn blazing sun!! No. Just do the hard, deep work beforehand. Bite the bullet and just do future you a solid here. By tackling the more difficult tasks ahead of your trip (reports, writing, a presentation… you know what your hard work is!) you chop out the stress of having to do it while you’re supposed to be exploring fun summer things. This way, you can focus on these cool experiences you’re having while handling simpler tasks during your “productive” hours. Make sense? Thought so.

Make the most of airport gates, trains and bus terminals

Ok, hear me out on this one. A rule I often travel with is to make the best use of airport gates, trains and buses. Does it take every ounce of willpower I have? Sometimes, yes. Do I love answering emails and filing invoices while I hear boarding calls blaring over the intercom? Nope. I do not. But, if I had to miss out on family time or turn down brewery hopping with friends the next day to do that same work, I’d enjoy that a lot less.

As a digital nomad, it's essential to use your time efficiently. Being on a bus, train, plane, or at an airport gate might not be the ideal work environment (I can’t argue there), but you can still use that time to get simple tasks done. That could be responding to emails, editing photos, doing light research, or organizing your files. By getting that small stuff out of the way during transit times when you’re sitting down anyway, you’re enabling yourself to be free and say yes (without guilt) to all the fun things you’re looking forward to upon arrival.

I’ve definitely played that game of should-I-or-shouldn’t-I? Only to let procrastination win. And seriously, there’s nothing more annoying than putting something off, having to say no to something fun, and thinking to yourself, “Ugh! I should have done it on the plan when I thought of it!” On the flip side, it’s pretty rewarding to clock some billable hours and earn back the price of your ticket as you fly to your destination!

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