Work Full-time, Travel Solo, Have Fun

The road to ultimate productivity when working remotely while travelling the world

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?

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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.

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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.

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 “resolving” 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.

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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.

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:

You become much better at your job. Whether it’s taking a data science course, reading case studies on hyper- growth companies, or learning SEO best practices, investing in developing a strong cross-functional skillset will invariably make you more effective at your job in the long run. Every time I read or watch something just because I want to learn about it, I always come away with a bundle of new ideas, even if that thing was only tangentially related to my job.

You’ll be happier. If you’re like me and enjoy picking up new skills and being productive, you’ll be a more outgoing, adventurous and happy person when you’re learning new things. I usually feel
pretty great after spending a few hours reading in a café or getting a machine learning crash course by the beach. But after binge-watching movies? Not so much.

It’s easier to meet people with shared interests. The more diverse interests you have, the more likely you are to have something in common with a stranger. More importantly, when you’re interested in learning something (especially if it’s related to tech or startups), you can almost always find groups on Meetup.com or elsewhere that are full of people who organize events centered around the topic.
This is a great way to meet and learn from people who share your interests. Much like the “Go To X To Do Y” strategy, setting aside time every day for learning is all about feeling like you’re
moving forward. By carving out time to pick up new skills, I work more effectively, stay happier, and enjoy my travels much more. Pack Light, Stay Mobile, And Make Logistics Easy It’s no fun when an airline loses your luggage. It’s even worse when an airline loses your luggage and you’re alone in a foreign country, don’t speak the language, have no contacts, and have a long list of unread work messages that you desperately need to check. You’re traveling solo, so you can maintain an amazing level of flexibility. You won’t end up using at least half of what you were originally going to pack, so ditch the suitcase, put that extra sweater you’ll never wear back in your closet, and go carry-on instead. I fit all of my belongings into one Deuter 65L travel pack and 25L Marmot
backpack. There’s plenty of space for everything I need, and I can carry everything comfortably on my back without trouble. Stay lean with your luggage and dozens of roadblocks that would’ve become huge pains will never happen in the first place.

Road warrior essentials:

Hardware, travel packs and SIM cards. Don’t get carried away. Pack light, but pack smart. The final thing I’ll add here is that travel logistics are way, way easier than you probably think, especially once you get a prepaid SIM card. These usually only cost USD15-USD20 for a few GB of data, and getting one is pretty much the first thing I do when moving to a new place (it’s also absolutely essential for working from the road). If possible, make sure you get a SIM card that allows tethering. For bonus points, you can also look into getting dual-SIM smartphones or 3G/4G routers.

With a working phone and the rapid global rise of Airbnb and Uber, not only can you typically find a nice, reasonably inexpensive place to stay within a few hours and get a ride there within a few
minutes, but you can do all of this from your phone, without ever taking your wallet out of your pocket. Sidenote: It pays off to do a little research on Airbnb hosts; if you’re in a country where you
don’t speak the language, finding a host who does (and who might share some of your interests) can make a big difference.
These solutions, coupled with the steady decrease in flight costs, mean that many of the pains associated with travel are quickly disappearing. You can decide to jump halfway across the world
tomorrow and have everything planned out just a few minutes later without breaking the bank.

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