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How to Spend Half Your Time Out of the Office Without Getting Fired

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Last Monday, I clocked in a full day working from 2 cities, 3 coffee shops, and my car. In a few weeks, I plan to do my job all the way from Belfast, and later this year, I’ll squeeze some workdays into the beginning of a trip to Hawaii.

Ahhhh, remote life. Sounds pretty great, right?

If you’re dreaming of a remote job—and even if you own your own business or work as a freelancer—you’re probably wondering if it’s actually possible to get work done with your mother-in-law on the next towel drinking daiquiris, or your partner in the driver’s seat listening to the radio.

Here’s the good news: It’s totally doable (and members of the Skillcrush team do it all the time!). But working remotely absolutely takes some planning.

If you don’t have a job that gives you the freedom to work remotely, find out what flexible work options are available to you—like a working vacation. Then make sure to sit your boss down and present your case, complete with your plans for availability, access, etc.

Once you’ve got the go ahead or—lucky you!—you’re already working in a remote job or pounding the pavement as a freelancer, here are some guidelines you should keep in mind:

Choose Wisely

For your first workcation, keep your sense of practicality at the forefront. You don’t have to sacrifice the feeling of adventure, but trying to get service with your phone tethered from a boat in a tropical storm isn’t the way to go—at least for your first time out.

Instead, opt for a more predictable travel situation, like a long weekend 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, you can think about branching out on more adventurous trips.

Gear Up

If you have a remote job, chances are you already trail your laptop everywhere like it’s an IV and never you 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. You absolutely can never have enough chargers.
  • Converters: If you’re traveling abroad, keep in mind that your gadgets may not be compatible with foreign outlets. Do your research—it can change country to country!
  • 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 far from home.

Find a Workspace

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.

Make a 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, and definitely not once you’re sitting on a beach somewhere. Coworkers are usually flexible, but only if you give them warning.

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 hangout, and when you’ll need down time to get work done. While you’re at it, 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.


Bring a Backup Plan for Contacts

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 or emails.

Don’t Forget Your 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.

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

  • 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.

Still stuck in your office? The quickest way to get a job that gives you the freedom and flexibility to make workcations part of your regular rotation is to learn in-demand digital skills. Get The Ultimate Guide to Landing a Remote Job and find out EXACTLY how.


Get Our FREE Guide to Landing a Remote Job You Love

Get Our FREE Guide to Landing a Remote Job You Love

Say goodbye to the 9-to-5. Learn the steps you can take TODAY to get a remote job.

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  1. Marc Replied

    I worked as a full time remote developer for 10 months in 2015 and I’m applying to do the same again. It can be quite isolating though; I went back to office work this year. But I think if I was disciplined enough, and perhaps actually took advantage of the travel flexibility this time rather than stay in my city, it could be awesome! There are some “remote first” companies about now, and NomadList.com is a beautiful site to behold if we’re getting serious. That dude did 12 startups in as many months… Inspiring.

    • Marc Replied

      Oh and there are plenty of good coworking spaces around now.

  2. Hillary Replied

    Thanks Randle! This was super helpful. I’m just starting my remote career and wish I would have read this before my headphones malfunctioned last week. A spare pair are now on their way! I have another tip to share. I am currently working from Uptown Minneapolis and have unfortunately hopped around to 3(!) different coffee shops/restaurants in the past hour but have learned a valuable thing in doing so: test the location’s internet strength and restroom availability prior to ordering that latte. I use SpeedTest.net and they have a handy mobile app, too. Only takes a minute. I use Google Hangouts for meetings and they recommend at least 1 mbps/2 mbps (up/down) for group video chats. If the test doesn’t hit that I move onto the next place. Hope this helps others and thanks again!  

    • Randle Browning Replied

      Hey Hillary! That is the best advice!! I always end up relying on my phone data or my Karma (it’s this data storage device you can use for WIFI), but a quick speed test is definitely cheaper! I always grab a seat and try to get online before I order too, so I don’t end up with a fresh latte and nowhere to sit. :P

  3. Kathryn Replied

    I love this! I’ve always had trouble cramming school work with vacation activities, and this article just puts everything into perspective for me in the simplest way possible. Thank you Randle for sharing!

    • Randle Browning Replied

      Thanks, Kathryn! So glad it’s helpful for you!

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