How to Work Effectively and Travel at the Same Time
A perfect example of some people playing and other people working along the Arno River in Florence, Italy. October 18, 2019.
Rarely do I have work days and off days—whether in a regular week, on a regular weekend, or when on travel.
I work when I can (meaning that I have a few minutes or an hour), when I must (given work deadlines and demands), and I work when inspiration or mood strikes (which it can for twelve hours on a Sunday—like last Sunday).
Though this sounds like I work all the time—and yes, on many days, it can feel this way as well—it does mean that I have a modicum of flexibility to do things I want to do on, say, a Tuesday.
Provided that the work gets done, gets done well, and gets done on time and on point—which includes ensuring that my team and my clients have what they need—I can structure my work to fit my life most of the time. This may mean I work a twelve-hour Saturday, because I took a light workday Tuesday. Or it may mean that I work six hours a day for a full week—including on the weekend—one week.
Flexibility matters most to me in work and in life. Fortunately, I mostly have it. I can work from anywhere with a good Internet connection and a computer.
With all the travel this site makes it look like I do—and trust me, I do less travel than this site makes it seem—I work on all these trips. Though I may have some travel experiences where I check in with work and stay available with work, and yet I mostly play, most of the time I travel and work full-time.
Think you’d like to take a trip—and still get all the work done?
(Side note: If you’d like a few tips on how I plan my trips, including my work-from-wherever travel, read my article filled with trip-planning tips and tricks.)
Plan the Trip
Yes, I mean fully “plan.” Although you need to give your plans air for flexibility—as chaos at work can always happen at any moment—if you like the type of travel where you spontaneously take each day as it comes, don’t try to work on vacation.
Working while traveling means keeping up with videoconference meetings and phone calls just as you would while in the office. Also, you have deadlines and work requirements you need to continue to meet. You will need to schedule the workload to ensure you get it all done as seamlessly as possible while away.
If you know exactly what you want to see and do on your trip, schedule it in around the work responsibilities. This may mean that you spend the morning at a museum—and then need to get back to the computer for the afternoon and pass up evening activities.
Also, it means that when you don’t have work to do, you need to maximize your opportunities. Your trip won’t have as much downtime as a pure vacation, because you will have two modes while working on a trip: seeing the place and getting the work done.
Take Longer Trips
When you travel and work, remember that you may travel, yet you also work. How easily we forget when we leave the office that the office hasn’t left us—at least not in working-remotely cases.
You will work for most of the day. You will not tour and travel and relax most of the day. As mentioned above, if you take a long lunch or skip out for an activity, you will need to return to the computer and catch-up later—or work longer the days before in preparation for the play time the day after.
For this reason, trips in which you work and play will require more time than play trips alone. You can really rock a city or a location in two or three days if you have nothing to do but tour it. However, if you work most of the time you travel, you’ll need more days to see and do the sites and things that drew you there.
Structure Your Days
When you know what you want to do each day and have planned out your trip, you can most easily structure your work and your play time. Consider adding another layer: Figure out the best possible flow for you for each day.
For me, I get up and get all my critical to-do tasks done with my morning tea. I don’t have a creative brain in the morning hours, so the critical thinking tasks and the deep pulls on my creativity wait until afternoon and evening. If I know I have an afternoon-only must-see, I may need to ensure I don’t book other afternoon must-sees on adjacent days.
It feels good to get up and straightaway plow through the e-mail, the files to review, the paperwork, and so on. I then know that, for the rest of the day, I can dedicate myself to the deeper work. (Other than responding to critical e-mail and last-minute team and client needs, of course.)
Also, the deeper work often has a little more flexibility in its deadlines and timelines, which means I can allow it to stretch over several days—if I plan carefully—and can skip out for dinner and come back to it at 10 p.m., if I so desire.
Expect to Miss Out
Unless you can stay in a place for as long as it takes to see and do everything that the place offers and to ensure you get in some level relaxation as well, working while traveling will mean that you won’t see and do all the things.
Some stuff just won’t fit the schedule.
And if you travel with other people, it will mean sucking it up when they leave for the day or the afternoon and you need to stay put and work. Also, it will mean that you will work while they nap, get exercise, and enjoy downtime—so, as mentioned above, you won’t really get any of these things (and so you’ll need to steel yourself not to feel jealous or resentful as a result).
If You Can, Do It
Some might argue that you shouldn’t bother going to a place if you can’t spend the entire time touring while there, yet I’d push back: If you can go somewhere—meaning that you have the time, the funds, and the bandwidth—and yet only see one big thing while there, do it.
Not everyone has the flexibility with their work to travel and get it all done at the same time. Frankly, I didn’t have this level of flexibility before FrogDog transitioned into a distributed workforce structure. Now that I have the flexibility, I love it. And I plan to continue to live it.
Go back into a corporate office full-time? No thank you.