I've been a telecommuting freelancer full time for more than a decade now, largely because it allows me the freedom to travel and live in fascinating places. Or, if I'm completely honest, because I wanted to be able to live a life where I could take work on vacation rather than take a vacation from work.

This month is being spent seeing as much of Greece as possible with my family during the day, while still writing and working during evenings, down time and travel between destinations. We take big trips like this one or twice a year along with several shorter ones.

Most of the time I don't bother updating clients or editors on my travels because it doesn't impact my productivity. If you were to look at my output over the years, you might assume you'd see dips in production during the times I was working from Ecuador for three months or Iceland for three weeks, but it's all pretty even, actually.

This is because of what I like to think of as mastering a mode you've probably heard others in the gig or startup economy refer to as "working like you're on vacation."

This mode doesn't only have to be for telecommuters trying to have it all from the road. Each time I get home from a trip I tend to quickly fall back into some bad habits that decrease working efficiency, because I can afford to, time-wise.

So I actually recommend experimenting with working on your next vacation because it will help you to identify some of your own bad habits that suck your time. For example, for me as a writer, a big one is online research that starts out as legitimately related to my project, but quickly turns into tumbling down a rabbit hole of distraction and outright procrastination.

Even if you don't have the geographic freedom to do your work from the road, you can simulate what working like you're on vacation. Simply take one day and do what needs to be done in one half or one third the time.

I know this sounds absurd at first, but think about how you would accomplish this if you absolutely had to. Everything depends on you pulling off the impossible this one day. It's putting yourself in this hard situation that forces you to take an honest, critical look at your level of efficiency.

The exercise of working on vacation has led me to strive to work like I'm on vacation, even when I'm not, to stay as productive and efficient as possible. Over the years I've developed four key principles to help stay in this mode:

Distractions must die: There's no hard out quite like having to catch a plane to get out of a country where your visa is going to expire soon. Just like when you're up against a deadline, the constraints created by travel can be very good for forcing you to focus. When I'm working on vacation, I tend to completely lose track of all the inanity of Facebook, Twitter, sports headlines and everything else that pulls my attention away from where it needs to be. If I take the time to get caught up later from home, I always find I didn't miss much.

Compartmentalize to survive: It's amazing how physically traveling away from the familiar can make you realize how much background pressure is working on us all the time. At home and work we are constantly reminded of tasks and chores that need to be done around the house, lunches we should have with friends, errands that need to be run. But on the road it's much easier to compartmentalize because you've got to focus on just understanding the foreign world around you. This effect seems to carry over to working while on vacation. When the more mundane cares of the world are thousands of miles away I get more and better work done on my projects. Getting in this mindset at home is tough but possible. It helps to have an office or other physical working sanctuary where those outside pressures aren't allowed to find their way inside.

Priorities in a straight line: When your time and connectivity is limited or uncertain as it is on the road, you better be ready to use it when it becomes available to you. This requires knowing your priorities at any given time. Lists are key here. When I have a moment on a bus or in a line, I always have access to my phone or a tiny notebook with my list of what needs to be done next. Sounds basic, but the time suck few of us admit to is the time we waste trying to figure out how we should be spending our time.

Be prepared to be lost: When traveling, nothing ever goes exactly according to plan. If it always does for you, I'm not sure you're actually doing travel right. More on that some other time. The crazy kicker to this rant is that, even as I've told you working like you're on vacation is about being productive in a fraction of the time, another key to making it work is to always allow for the possibility that you'll have even less time to get your tasks done. Because, let's be honest, this is happening in our normal working lives all the time anyhow. On the road, getting lost in an unfamiliar city is a good way to lose an hour of work time, but I often find that those unplanned and often uncomfortable experiences tend to yield other ideas and insights, like the idea for a column about working like you're on vacation, for example.

Published on: Jun 20, 2017
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