Work on the Road: Secrets to a Successful Workcation

Work on the Road: Secrets to a Successful Workcation

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Though 60% of the American workforce works in-office, remote work has gained momentum in recent years. Full-time remote workers, in conjunction with hybrid employees, have come to value the flexibility, savings, and work-life balance that remote work allows. The workcation, for instance, has emerged as a practical byproduct of remote access and flexible living.

What is a workcation?

A workcation is a working vacation that combines work time with leisure. It does not require taking personal time away from the normal work schedule. The work day and all relevant tasks are accomplished without disruption outside of the office, typically via an internet connection.

Brian and I have had some practice fine-tuning our workcation approach. We have consistently worked remotely since 2015 and have optimized our strategy to find the balance between effective productivity and off-the-clock enjoyment. This isn’t to say that we don’t ever have 13-hour work days in a hotel room, but rather that we are where we choose to explore once we clock out.

A workcation is a give-and-take kind of situation; we embrace it as a creative way to earn a paycheck and be able to travel at the same time.


Workcation Like a Pro

My first experience working remotely was in 2007; I was hanging solo on a spring break trip and opted to log into work for part of the week. Times have changed a bit since then, especially now that my workcations include a partner (and fellow remote worker), though key fundamentals remain the same for the most successful experience.

Follow these proven tips to accomplish more and excel as a productive employee and traveler on your next workcation.

Carry-On Your Work Essentials

Keep your work on your person. Be vigilant about your possessions, specifically what’s required for you to do your job. Hiccups can happen during travel, especially when flying. Minimize the stress and fuss of potential lost luggage by carrying on your essentials. Brian and I actually prefer to travel with carry-ons only because it’s faster and easier than lugging around extra luggage.

Seek a Comfortable Space

Social media would like you to believe you can realistically do your job on the beach. And maybe you can, but that’s definitely not where I go when I need to concentrate. It’s important that your workspace is an area that encourages deep focus and productivity. A quiet, calm location free from distraction with a fast and reliable internet connection is my trusty go-to work environment.

Always Have a Backup Plan for Internet Access

When you travel from place to place, you’re bound to experience a spotty internet connection at some point. A poor internet connection can seriously impact a day’s worth of work, if not more. Having a backup plan ensures that you stay on task and keeps your employer happy.

Whether you choose to tether your devices with your own mobile data plan, purchase a Wi-Fi hotspot, or, like us, visit your local library to check out a Wi-Fi hotspot, you’ll find yourself breathing a lot easier when you run into internet issues.

Protect Your Data

Don’t let your private information leak out to anybody and everybody! Stay protected with a virtual private network (VPN) to maintain your digital privacy. A VPN encrypts and secures your data so that only you and authorized websites can access it. We recommend a VPN for both personal and business use.

If you’re self-employed or your employer doesn’t require a VPN connection to log into work, it’s a great idea to install and use one anyway. Be sure to check with your employer to ensure a VPN is permitted before using it.

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Stick to a Work Schedule

Brian and I maintain our normal work hours wherever we are. This routine keeps us focused on our work day and committed to capitalizing on our free time.

One would think time differences would complicate our travel plans, but that hasn’t been our experience. In fact, we have learned that we especially enjoy visiting the west coast while working east coast hours; we begin our day way before the sun rises and still have plenty of time to take on the day after work. Our adventure through Alaska is one example of how we made the most of our east coast schedule.

If you find time differences to be cumbersome during workcations, check with your employer to see if they’re willing to accommodate alternate work hours. Some offer more flexible arrangements, which could be beneficial to you if you plan to travel to a different time zone.

Keep Your Charging Cables Handy

Be sure to have all necessary charging cables on hand. Better yet, bring along a battery backup just in case! You don’t want to risk not having enough juice to complete your work day. Brian and I make sure we have car chargers, cables, and a battery backup whenever we hit the road. They’ve all come in handy for us, whether we’re at the airport, on a road trip, on a train, or even out in public.

Intentionally Plan Your Free Time

It’s not a great feeling when you wrap up a work day somewhere new and you’re so drained that you’re unable to bring yourself to explore the world outside. Not only does this defeat the purpose of a workcation, it also undermines the value and knowledge one gains from personal experiences.

Plan your free time wisely. If you are in an area that has a lot to offer, then budget your time to include more than a week’s stay. That way, you at least have a full weekend to explore. Some workcationers choose to stay a month or two in one location. It all depends on what you’re interested in and how you prefer to travel.

Plan Ahead

To be intentional with your time, you must plan ahead. Be mindful of scheduled meetings, hard deadlines, and extracurricular commitments. You don’t want to plan for an afternoon of sightseeing if you have meetings that might run late. You also probably don’t want to hop on an important video call while you’re traveling in a car.

It took Brian and me some time to settle into a rhythm of balance and compromise. Truthfully, workcations help us detach from our workaholic tendencies. In the past, it wasn’t uncommon to find us both glued to our laptops and pulling 10+ hour days with minimal (if any) breaks. Planning ahead is crucial to our workcations as it allows us to:

  • Break for meals as needed
  • Decide who has the flexibility to drive while the other works (especially on road trips!)
  • Secure reservations for tours and activities
  • Commit to a clock-out time
  • Better manage heavier workloads for optimal efficiency
  • Create loose itineraries that can quickly be adjusted
  • Keep in mind the days that offer flexibility for longer work days as needed (for work emergencies!)
  • Be excited for the plans ahead

Find Your Balance

Everyone is different and has different points of equilibrium. If you’re new to workcationing, you’ll discover if it’s right for you. It takes effort, experience, and trust to find a true balance between work and vacation. Our tips above, along with self-discipline and motivation, can help you achieve a successful trip while working remotely.

There’s so much to see in this world. If you can explore while crushin’ a 9-to-5, you’ll be able to see more, do more, and learn more in an affordable way and still earn a paycheck!

If you’ve taken a workcation before, did you like it? Why or why not?

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2 Responses

  1. Since I had to work in downtown Atlanta, it was a smart decision to arrange my hours to be 5AM to 1:30 PM to avoid the traffic. When I got home I would log in to work and put in a couple more hours, either working on one of my projects or just monitoring how everything was going. This ‘remote’ work expanded in my last few years to traveling with the wife, and working wherever there was internet. I carried my intenet headset with me and was able to attend meetings and otherwise communicate verbally when it was required. One time I was contacted while driving for an emergency, it required that I log in and manage an incident. Well the first place I found with an internet connection was a McDonalds along I65 in Alabama. So, I’m on-line and verbally connected to an outage team, when suddenly a dozen or so 5 and 6 year olds come screaming into the restaurant for a birthday party. Everybody on the call got suddenly quiet. Then somebody asked “where are you?”. Busted!!!

    1. Remote work offers such awesome flexibility. It’s really nice to have the ability to avoid heavy traffic—or a commute altogether. Though it can definitely affect the work-life balance, especially when you’re the one handling work emergencies.  Middle of the night issues? International meetings? Whatever the time and responsibility, it’s often directed to us remote workers.

      Still, I find remote work much more productive and enjoyable than going into an office. Even when it unexpectedly happens at a fast food restaurant off the highway 🙂 Great story. Thanks for sharing!!

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