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How to Spend Half Your Time on Vacation without Getting Fired

How To Be Great At Your Job...Even At The Beach - Skillcrush

 

Last Monday, I clocked in a full day working from 2 cities, 3 coffee shops, and my car.

Ah, remote life. It sounds great, doesn’t it? And it is. In a few weeks, in fact, 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.

Working remotely can give you the freedom to prioritize your work without putting your life on hold, and vise versa.

But 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 REALLY possible to get work done with your mother-in-law on the next towel drinking Mai Tais, or your husband in the driver’s seat listening to sports talk radio.

It’s totally doable (and members of the Skillcrush team do it all the time!), but it takes some planning.

First off, 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. Then make sure to talk to your boss about the possibility of taking a workcation—or traveling while on the job.

But if you’re already working in a remote job or pounding the pavement as a freelancer, and you’re SO ready for your first workcation, here are some guidelines you should keep in mind:

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.
  • 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

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 hangout, 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.

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. ;)

 

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6 comments

  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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