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8 Proven Strategies for Working (and Being More Effective) While Traveling

by Randle Browning
featured, money & life

Balance Your Time When Working While Traveling on Vacation

Randle Browning is the Director of Content at Skillcrush, an interactive online community that makes learning life- and career-changing digital skills approachable and fun. When Randle’s not dreaming up new content marketing strategies at her remote job, she’s reading a good book or putting vegan food on Instagram. A version of this post first appeared on the Skillcrush blog.

When I got hired in my remote job 2 years ago, I had no idea what I was getting into. I didn’t know about video meetings and team chat rooms, I had never thought of the cloud as something besides a place to store pictures of my dogs, and I didn’t know what it would really look like to “work from home.”

10 years ago, “working from home” meant doing some version of data entry or customer support, or maybe hosting parties to sell mountains of Mary Kay makeup or Tupperware (raise your hand if you kind of miss those parties).

But these days? You can do the vast majority of jobs—from coding to marketing to teaching—without ever setting foot in an office. With tech tools like live video calls, team chat, and company cloud storage, you can attend meetings, collaborate on projects, and even share materials with a team across the world.

But do you want to know the real secret about getting a job “working from home”?

When you ditch the physical office building, you don’t just get the opportunity to work from your couch—you get the freedom to work from anywhere.

For you, that might mean clocking in from a coworking space, your home office, a cozy local coffee shop, the park (hello, portable WIFI), or, my favorite…from your vacation.

It’s true! In the last 2 years, I’ve traveled to a rural lake in Canada, the beaches of Maui, my cousins’ house in Belfast, a football game in Dallas, and Newport Beach, California, without taking a single day of vacation.

And while it’s great to take TRUE time off, with a flexible remote job, you don’t have to limit yourself to traveling for a measly 2 weeks a year.

That said, traveling while working, or taking a “workcation,” requires some planning ahead. After all, how are you truly going to get any work done while sipping Mai Tais on a towel with your in-laws? And what happens if your hotel Internet turns out to drop in and out based on the kid in the game room live streaming on the XBox?

Tips on Working While Traveling on CreativeLive

Well, after all those trips, I’ve picked up a few workcation best practices that can save you from missing meetings (or upsetting your mother-in-law), and make sure you manage to have a great time on your trip as well:

If you’re ready for a great remote job, check out this free downloadable ebook, The Ultimate Guide to Landing a Remote Job You Love and be sure to sign up for our class with Darren Murph on Working Remotely.

1. Choose Wisely.

For your first workcation, go to a place where you’re not going to end up in a rickety van with a dude named Panda during a tropical storm with your phone tethered to your laptop and your best friend covered in pox….at least for your first trip.

Instead, opt for a more predictable travel situation, like a long weekend trip in a hotel with WIFI, or spending a workweek in a big city (with lots of coffee shops, WIFI signals, and electronics stores).

Once you’ve tested your wings working remotely from a hotel or well-populated area, think about branching out on more adventurous trips.

2. Get the Gear.

If you have a remote job, chances are you already trail your laptop everywhere like it’s an IV and never leave the house without your charger and headphones.

But when you pack for a workcation, you should prepare for the worst.

Bring a hard drive: Especially if you’re working with media, storing big files on a hard drive protects you in case you need to work without an Internet signal, or you can’t access files in the cloud.

Bring extra headphones: Since you need headphones to clock in to meetings on Skype or Google Hangout, make sure to have a backup pair just in case you drop yours in the jacuzzi.

Figure out your tethering situation: Make sure you can login and work from anywhere, even without a WIFI signal. Set up Bluetooth so you can tether to your phone, update your mobile data plan for travel, and consider investing in a data storage device like Karma.

Chargers: It’s an obvious one, but make sure you have a charger and/or connecting cable for your laptop, phone, and hard drive (bring extras).

Clean your laptop: To minimize the risk of total tech meltdown, clean files off your laptop and sort out your cloud storage in advance.

Figure out your tech setup: Will you be calling in to meetings from your phone? Test it! Will you tether to your phone while traveling in a bus? Try that out in advance. Will you bring a tablet and a portable keyboard? Make sure your setup works before you find yourself in the jungle.

3. Make Sure You Have a Space to Work. 

Best Gear to Bring on a Working Vacation via CreativeLive

Just like testing out your tech setup is a smart move, you should also do everything you can to plan ahead when it comes to your workspace. That might mean asking the hotel if your room has a desk and chair, scoping out coffee shops near where you’re staying, or asking a family member about the quality of their Internet connection.

4. Figure Out Your Schedule Ahead of Time.

Look at your work calendar, then make sure your travel plans don’t interfere. If they do, move meetings and deadlines in advance.

It’s also a great idea to check in with the people you’re traveling with to set expectations about when you’ll be available to hang out, and when you’ll need “alone time” to get work done.

5. Tell Your Team About Your New Time Zone. 

When you’re planning your schedule, take some time to send an email to your teammates or clients letting them know what time zone you’ll be in, and when you expect to be available. Also let them know how they can reach you when you’re not online.

6. Bring a Hard Copy of Passwords.

If you’re like me, all your passwords are stored in a trusty password manager. But make sure that even if you get locked out of your password manager, you’ll have a hard copy of all the most important ones.

If you’re worried about your passwords being stolen, it’s far more likely that you’d be hacked than that someone would find a password in your purse and sell your identity. Even so, I tend to write my passwords in code and hide them in random pockets in my bag. Why miss an opportunity to feel like a spy?

7. Have a Backup Plan (Phone Numbers of Coworkers).

If your laptop crashes or your phone falls off Mount Kilimanjaro, how will you tell your coworkers you’re alright but you’ll probably miss the meeting? Go old school and keep a hard copy of your teammates’ phone numbers. That way you can still get in touch if something goes wrong (like if you end up in the van I mentioned above).

8. Balance Focused Time with Free Time.

Balance. If finding work-life balance is tough on a normal day, it can be even trickier on a workcation. And finding the time to commit to work without destroying your vacation (and making everyone you’re traveling with hate you!) is probably what you’re most worried about.

8 Proven Strategies for Working and Being More Effective While Traveling

To be smart and savvy about balancing your work obligations and leisure time, try this:

Work during “off” hours depending on the time zone. Instead of turning down that hiking journey in Nepal, spend the day on the mountain and spend the evening getting work done.

Do rote tasks while you’re distracted. If you’re lounging on the beach with friends, take that time to do rote tasks that don’t take much of your brain power.

Do tasks that require focus alone. If you need to be totally “there” for a certain task (like writing a blog post or attending a meeting), make sure you schedule alone time to get that work done.

Set limits. Don’t be afraid to say, “I need 1 hour to do this thing.” It’s okay to shut yourself up in the hotel for 2 hours if it means you can spend 3 enjoying dinner and drinks later.

Take some days TOTALLY off. Schedule a few days with no work at all, even if it means you have to put in extra hours before or after your trip. After all this double-dealing, you’ll need (and you’ll have EARNED!) some time off. Taking some time to rejuvenate will mean you’re fresh and on point when you do clock in.

And remember: if you get your work done and remain calm, chances are, your boss will go with the flow. And if something does go wrong? Let your team know and enjoy the trip! You’ll be home soon, and since you work remotely, you’ll be able to catch up on your own time.

Psst!! Are you ready for a workcation, but need a remote job first? Check out this free downloadable ebook, The Ultimate Guide to Landing a Remote Job You Love. Once you do that, be sure to join us for Work Remotely: Thrive in a Job from Home right here on CreativeLive.

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Randle Browning

Randle Browning is the Director of Content at Skillcrush, a digital education company for getting the tech skills you need to make a major career change. She’s kind of obsessed with Instagramming her vegan breakfasts.