Life Hacks

Going Mobile: 10 Tips for Working On the Road

Working From Home 2.0: Travel Telecommuting

It’s 2015, the height of the work from home era, and you’re ready to take things to the next level. Sure, working remotely from your bedroom has its perks, but you’re bored of it. What’s the point of slaving from home when there are dozens of magical and faraway places just begging to be worked in? You have the itch and it must be scratched. As you plan your getaway and gear up to see if you have what it takes to telecommute from the ever precarious and always changing environment of the long, open road, take my advice and brace yourself. Working on vacation is harder than it sounds.

Working on the Road with Veysey

Having spent the majority of my post-graduate life working from the road, I’ve learned a thing or two about getting things done while still making plenty of time to enjoy the people and places along my way. It’s not easy, but it must be done. You’ve made it this far and there’s no turning back. So, grab a cup of coffee and fuel your next adventure with these ten foolproof mobile telecommuting tips.

Working From Home on the Road with Veysey

1. Assess (and Re-Assess)

After setting dates for an upcoming trip, consider it’s impact on your workload and determine what tasks will require completion. Consider this the pre-planning stage. Assess the big picture and set yourself up for success by answering the following questions pertaining to your work and trip.

Telecommuting from Peak 9 Breckenridge Colorado

Define Your Trip

  • How long will you be gone for?
    • Depending on how predisposed you are to last-minute plan changes, the type of trip on which you are embarking, and your medium of transportation, the length of your trip may change as you go. Whether you’re traveling by car, bus, or plane, changing your departure date can often be easier than saying no to something you really want to do. Unless you have somewhere really important to get to by a certain date, be prepared to cater to your whims. What started as a weeklong trip can easily turn into a month-long adventure and you shouldn’t have to deny yourself.
  • How much time do you have between now and your vacation?
    • Is it a year from now or two weeks from now? How much time you have left until departure will help determine how many extra work hours you can realistically squeeze in prior to commencing your trip.
  • Where will you be staying?
    • Will you be in a friend’s home with reliable wi-fi or a in a remote jungle village somewhere in Indonesia? Will you be changing locations? How often will you have to move?
  • What activities will you be engaging in?
    • Are you mostly enjoying lazy days on a desert island beach with access to internet whenever you want it, catching up with city friends over nightly euro trash club excursions that leave your brain sad the following morning, or hiking miles of wilderness with intermittent breaks of civilization?
  • Will you be experiencing extended periods of time away from your phone or computer?
    • How long do you expect to be disconnected from reality and in what sorts of time increments?

Define Your Workload

  • What tasks do you need to accomplish during the course of your travels?
  • Can these tasks be broken up into smaller parts?
  • How long do each of the tasks that you have to address generally take?
  • How many unexpected tasks typically arise in your job and how long will they take?
  • Will you have to take meetings and phone calls while away or can you reschedule them?
  • Are there parts of your job you can outsource or will you have to do everything yourself?

Mobile Telecommuting Road Trip with Kelvin

2. Devise a Strategy

Using your answers to the questions above, create a schedule for tackling your workload. Take the amount of time you estimated your tasks will take to complete and multiply it by 1.5 (or 2.3 if you have a difficult time focusing). Then, based on the new amount of time each of your tasks will require and the general nature of your trip, come up with a day by day breakdown. Block out periods of work that you can dedicate to sitting down with your computer in an acceptable work environment without distractions.

3. Outsource

If you’re one of the lucky few whose jobs are able to be broken up into distinct parts and handed down to an eligible contractor, then take full advantage of the perks with which this provides you and give away as much work as you can manage, while still earning enough income to support yourself. Find an intern at your local university or choose a contractor using sites like

4. Set Specific Goals

Blocking out periods of work and identifying the tasks that need completing is not enough to assure that deadlines are met and deliverables delivered. In each of your scheduled time blocks, specify which tasks (or pieces of tasks) will get done when. Always place the most difficult and most important tasks earlier in the schedule and at the beginning of each work period. If worse comes to worse, easier, less offensive tasks can be outsourced or dealt with at a later time.

5. Know Your Dead Zones

Don’t get side swiped by a dead zone when you’ve blocked off time to work in the car, the wilderness, or a small town on the outskirts of civilization. The last thing you want is to re-plan your entire task schedule because you forgot to check your mobile carrier’s wireless service map. Know where you’re likely to experience outages and when in doubt ask friends or avoid scheduling work time in areas with suspicious service quality. Small, high-elevation towns situated a good distance modern society are generally good indicators that you’ll experience poor mobile reception and less-than reliable internet access.

Telecommuting from the Road in Glacier National Park Montana

6. Work in the Mornings

If you don’t work in the mornings, you may never work at all. Procrastinating your work hours to the second half of the day can result in a series of unwanted and unexpected consequences such as never making it to work, arriving late, or being too exhausted to concentrate.

Telecommuting iPad Peak 9 Breckenridge

7. Keep Your Devices Charged

You never know when you might find a moment to knock a few tasks off your list. So, incase you experience unexpected instances of downtime during which you can pull out your iPad and answer a few tweets or get on the computer and crank out emails, be prepared with battery life. You don’t want your phone to die five minutes into using it as a hotspot.

8. Know Where You’re Going to Work

Pre-planning your work locations can save you a lot of time. Based on where you are most likely to be during each of your scheduled work periods, consult Yelp to see what productivity friendly businesses are available for you to hang out in. Think coffee shops, restaurants, libraries, co-working spaces or anywhere that will let you to place yourself in a mental space conducive to doing something boring while fun to be had is knocking at your door. Make sure to double check that your spots of choice offer wi-fi.

9. Check Closing Times

Closing time is an easily avoidable detriment, so go online, check Google Maps, or set your Yelp filter to weed out any place closing before your scheduled finishing time. On our recent trip to Portland, my partner Samantha and I arrived in a cafe at 3pm only to be made painfully aware that it was set to close at 3:30. After having already spread out all of our belongings, we were not stoked to close up shop before barely even beginning. Do your due diligence and don’t let closing time happen to you.

10. Choose the Right Wireless Carrier

When working from the road, your mobile carrier is your best friend. Select one with a reliable network that covers where you’re going to be. When I first arrived in Montana several years ago, I was still a loyal and long-time customer of AT&T; a provider that had served me just fine in Cleveland, but which was surprisingly precarious across large portions of the wild western frontier. I was disappointed to learn that in areas where my Verizon toting friends had perfect service, my lowly AT&T coverage suffered immense inadequacies and frequent dead zones. Despite the inconvenience,  at the time, I was not yet ready to make the leap to the nation’s largest network. I was locked in to a two year contract, my iPhone was due for an upgrade soon, and in an era when data still cost an arm and a leg, I was decently satisfied being grandfathered into one of AT&T’s early unlimited data plans. But that was then, and this is now. Today, most, if not all of the major carriers have nixed two-year contracts and are no longer offering free bi-annual phone upgrades. There is little to stop us from shopping around and selecting a wireless network that works when we need it. Take a look at the coverage map to see who is doing what well in your area.

Cell Phone Carrier Coverage Map


Make Mobile Telecommuting Work for You

Working from Home on the Road with Cuiksa

As more people enter the world of telecommuting, and paid time off slowly becomes a thing of the past, the already fine line between work and play will get progressively blurrier. But with the freedom of never having to ask permission for holiday comes the inability to ever fully disconnect from everyday life. Working while traveling is thus becoming increasingly more common, and since traveling is an involved and time-consuming commitment, working from the road is generally less pleasant and more complicated than we would like it to be.

Working from Home On the Road in Jackson Wyoming with Dogs

Sure, there is always the wake up at noon, shower, have breakfast and proceed to lounge at hip coffee shops sipping honeyed-up Americanos with your fellow work at home girlfriends scenario. More often than not, however, working from the road means making haphazard use of what precious time you can find to complete pieces of task as quickly and efficiently as possible while running around, packing, unpacking, answering phone calls, typing text messages, juggling schedules, and engaging in various other novel and sometimes unusual activities. Distraction lurks around every corner and it’s up to you and you alone to stay focused.

Working from Home Breckenridge Colorado

In proving much more difficult than we would at first like to believe, working from the road, even more so than working from home, is a skill that requires careful honing and serious dedication. When you’re confined to a windowless cubicle with your computer being the only thing to look at and Sally, the annoying middle-aged lady from three desks down your best option for social interaction, finding salvation in your work may be the only thing left between you and insanity. Take that all away, however, and getting yourself to focus on work can be at the very least a little tricky and at most, downright impossible. Surrounded by a slew of new friends and old, combined with the endless swirl of captivatingly novel environments all simultaneously demanding your attention, you will find that focusing on work is a more challenging task than you ever thought possible. Using the ten true and tried tips presented above, however, you can tackle telecommuting from the road head on and set yourself up for a successful experience.

Share Your Story

Have you worked from the road or are you an expert mobile telecommuter? We want to hear your stories, tips and advice! Share your experiences, concerns and successes in the comments below and let us know how we can better our work-ations.

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