
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 Randleâs not dreaming up new content marketing strategies at her remote job, sheâs 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 didnât 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 didnât know what it would really look like to âwork from home.â
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10 years ago, âworking from homeâ 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 jobsâfrom coding to marketing to teachingâwithout 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 âworking from homeâ?
When you
ditch the physical office building, you donât just get the opportunity to work from your couchâyou 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.
Itâs true! In the last 2 years, Iâve traveled to a rural lake in Canada, the beaches of Maui, my cousinsâ house in Belfast, a football game in Dallas, and Newport Beach, California, without taking a single day of vacation.
And while itâs great to take TRUE time off, with a flexible remote job, you donât have to limit yourself to traveling for a measly 2 weeks a year.
That said, traveling while working, or taking a âworkcation,â 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?

Well, after all those trips, Iâve 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 youâre 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 poxâŚ.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 youâve 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 itâs an IVÂ and never leave the house without your charger and headphones.
But when you pack for a workcation, you should prepare for the worst.
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Bring a hard drive: Especially if youâre working with media, storing big files on a hard drive protects you in case you need to work without an Internet signal, or you canât access files in the cloud.
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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.
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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.
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Chargers: Itâs an obvious one, but make sure you have a charger and/or connecting cable for your laptop, phone, and hard drive (bring extras).
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Clean your laptop: To minimize the risk of total tech meltdown, clean files off your laptop and sort out your cloud storage in advance.
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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.Â

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 youâre 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 donât interfere. If they do, move meetings and deadlines in advance.
Itâs also a great idea to check in with the people youâre traveling with to set expectations about when youâll be available to hang out, and when youâll need âalone timeâ to get work done.
5. Tell Your Team About Your New Time Zone.Â
When youâre planning your schedule, take some time to send an email to your teammates or clients letting them know what time zone youâll be in, and when you expect to be available. Also let them know how they can reach you when youâre not online.
6. Bring a Hard Copy of Passwords.
If youâre 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, youâll have a hard copy of all the most important ones.
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If youâre worried about your passwords being stolen, itâs far more likely that youâd 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 youâre alright but youâll probably miss the meeting? Go old school and keep a hard copy of your teammatesâ 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 youâre traveling with hate you!) is probably what youâre most worried about.

To be smart and savvy about balancing your work obligations and leisure time, try this:
Work during âoffâ 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 youâre distracted. If youâre lounging on the beach with friends, take that time to do rote tasks that donât take much of your brain power.
Do tasks that require focus alone. If you need to be totally âthereâ 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. Donât be afraid to say, âI need 1 hour to do this thing.â Itâs 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, youâll need (and youâll have EARNED!) some time off. Taking some time to rejuvenate will mean youâre 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! Youâll be home soon, and since you work remotely, youâll 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.