Productivity On The Road: Work Full-Time, Travel Solo, Have Fun


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I’ve traveled solo while working full-time for ten-plus months, across more than 15 countries. It’s one of the most fun and rewarding things I’ve ever done. My work breaks over the past year have included things like scuba diving in Belize, polo lessons in Buenos Aires, music festivals in Hungary, and more.

Working full-time while on the road is not easy, but it’s definitely a skill that can be mastered over time.

For those interested in the nuts and bolts of how to travel while working, there are already several great articles out there explaining how it’s done. If you’re not familiar, I recommend starting with Toptal COO Breanden Beneschott’s guide.

In terms of logistics and planning, pulling off a full-time work schedule while on the road is much easier and cheaper than you probably think (at least in my experience), and the infrastructure for doing so continues to grow rapidly.

However, the following problem is far more difficult to solve, especially when traveling solo: Can you fully enjoy your travels while not sacrificing the quality of your work?

Striking The Right Balance

Can you navigate travel logistics, work full-time, and take care of yourself physically and mentally, all while setting aside enough time to explore the places you’re visiting, find fun things to do, and meet new people?

Since you won’t have much of a support system when you’re alone in a foreign country and (usually) don’t speak the language, finding the right balance is critical. Your routine has to be sustainable in the long run, and if you aren’t careful, things can go downhill in a hurry.

As I’ve been traveling, I’ve gotten a lot of questions from friends and colleagues about the psychology of this lifestyle, including everything from how to avoid loneliness to how to maximize productivity.

It’s not for everyone, but this lifestyle can be both incredibly fun and extremely productive, provided you figure out how to do it in a way that works for you. As I’ve traveled, I’ve noticed some key habits, mindsets, and tricks that are important for anyone who is considering working and traveling to keep in mind, regardless of their occupation or interests.

This post covers some of the most important strategies I’ve picked up while on the road.

Go To X To Do Y

When you have the option of living anywhere, it can be difficult to choose a destination, and going to places to see/do touristy things can get old fast. I’m a big fan of going to places to do specific (non-touristy) activities, as opposed to just going to places that sound interesting on paper.

In the past months, I’ve gone to:

  • Portugal to learn how to surf.
  • Berlin and Zurich for conferences.
  • The UK to take a trip through Wales.
  • Santorini to join friends who were on vacation.
  • Israel to visit family and work on my Hebrew.
  • Belize to learn how to scuba dive.

Brazil, Uruguay, and Argentina for the Toptal Roadtrip.

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Working full-time and traveling the world might be easier than you think, especially when you’re traveling for a purpose.

I’ve found that having a purpose to your travels leads to a few great outcomes:

  • It’s a lot easier to structure your time and priorities.
  • It’s easier to meet fascinating people with shared interests.
  • You learn amazing new skills that you’ve always wanted to learn.

When you’re traveling solo and devoting a lot of time to work, it’s important to limit the extent to which you’re “re-solving” the same problems on a daily basis. What I mean by that is, you don’t want to find yourself waking up every morning without any plans for where you’re going to work, what you’re going to work on, where you’re going to eat, who you’re going to meet, what non-work things you’re going to do, and so on.

Not only is it easy to waste a lot of time and energy answering the same questions over and over again, but it will also quickly make you feel like you’re swimming in circles without accomplishing much.

To be clear, I am just as strongly against doing anything that’s “too organized” while traveling. I’m pretty averse to resorts, guided tours, and so on.

As a good friend of mine likes to say:

“I always love seeing big cruise ships. The more I see of them, the fewer people there will be wherever I am.”

The adventure and uncertainty of traveling is half the fun, and it’s important not to lose sight of that by planning too much.

In short, don’t just go to Thailand. Go to Thailand to motorbike from Bangkok to Chiang Mai. Go to Brazil because you’ve always wanted to experience Carnival. Go to Nepal because you dream of hiking the Annapurna trail.

The possibilities are endless, and it’s when you go somewhere with a goal in mind that things begin to take off.

Set Aside Time Every Day For Learning

When you’re working at a startup, there are always a million different tasks that need to be accomplished, and you’re constantly in a race against time. You can easily spend all of your waking hours knocking things off of your to-do list, and with so much that needs to get done, it can be hard to justify investing time in anything that’s not the task at hand, or at least directly related to the task.

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Being on the road is no excuse for complacency. You can work, play, and master new skills, just as you would from home.

However, taking time each day for the explicit purpose of improving your skills and learning new things has a profound and positive impact in several important ways: Continue reading “Productivity On The Road: Work Full-Time, Travel Solo, Have Fun”