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.
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.
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 cafe 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.
Stay lean with your luggage and dozens of roadblocks that would’ve become huge pains will never happen in the first place.
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 $10-20 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). This Wikia page is a great resource for an accurate overview of pre-paid SIM card options in most countries. 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.
Take Care Of Yourself: Exercise And Eat Well
This isn’t exactly a huge revelation, but it’s important. When you’re abroad, your support system is minimal, so it’s critical that you invest in making your lifestyle sustainable. This goes both ways: Working non-stop is as dangerous over the long run as failing to work at all.
My colleagues at Toptal are extremely smart and impossibly efficient, and teams here strive to move very fast and execute ruthlessly. What may be high priority one week will no longer be relevant the next. Everyone needs to not just keep up, but actively push things forward, and the occasional psychological strains of travel can’t ever get in the way of that. In this type of environment, you absolutely must take the time to take care of yourself. Even small habits such as being mindful of posture or buying boxes of protein bars can make a big difference when you don’t have time to eat and need to be operating at a high level. If you’re working at a computer all day, you need to be taking a few minutes every hour or two to at least do some basic bodyweight exercises.
If you’re spending an extended period of time in a new city, a good habit to develop is to spend time familiarizing yourself with the grocery stores and markets in your neighborhood. Cooking regularly saves you time when you need to focus on work, and can really help keep costs down. If you’re concerned about food quality or have dietary restrictions, it will also pay off to do some research on destinations ahead of time.
Aside from watching what you’re putting into your body, taking care of yourself means that you need to carve out time for regular exercise and figure out a reasonable sleep schedule to which you’re going to stick. Note that this definitely doesn’t mean your schedule has to be “normal”—you don’t have to simulate an office-to-gym-to-dinner-to-bed routine. Being able to design your own schedule is one of the major bonuses of a flexible lifestyle, after all. There are people who do their best work in the dead of night and sleep in every day, but the point is that they choose habits that are sustainable for them.
Exercising while traveling can be very easy or very hard. While it can be annoying to find a new gym every time you move to a new place, traveling solo means that you can specifically seek out places where adopting a healthy routine comes naturally.
For me, this means getting an apartment by the pickup basketball courts in Tel Aviv or a place on the beach by a surf school in Lisbon. Figure out what you like doing that’s fun and also healthy, and then go somewhere that makes it really, really easy for you to do it.
Join Communities Of People With Shared Interests
As I pointed out earlier, the infrastructure that is available around this nomadic lifestyle is growing rapidly, and I’m curious to see what things will look like a year from now.
For people who don’t have a travel partner but are wary of going it alone, there are options such as Hacker Paradise or Remote Year that invite you to join small communities of people who are also working from the road. There are also many combined co-working and co-living spaces establishing footholds in exotic locations around the world, including the Surf Office in Lisbon and Gran Canaria, for example.
In terms of online communities and meetup groups, in addition to Meetup.com, groups such as InterNations and the Hashtag Nomads Slack community are good ways to making friends in new places. However, in my experience, none of these compare to the Toptal Community when it comes to finding people to meet up with for trips, events, or just a nice dinner.
Regardless of whether you choose to be a part of such communities, it’s useful to know that they’re there if you need them. The infrastructure for making friends exists in most sizable cities around the world if you know where to look.
Spend Time Traveling With Coworkers
This is especially important if you’re new to a company, or if you are just starting your career and need to do everything possible to learn as fast as you can.
Every time I’ve visited or traveled with colleagues at Toptal (who are located in over 100 countries), not only has it been incredibly fun, it’s also led to immediate and substantial jumps both in my understanding of different aspects of the company and in the quality of my own work.
There’s so much to learn from spending full weeks traveling, having meals, and working with colleagues across the company, and it always leads me to intriguing new ideas. The Toptal Roadtrip and the Toptal Academy React Course (that 200-plus Toptalers are currently completing) are two initiatives that have been a direct result of spending time visiting colleagues.
Moreover, the chemistry you build by traveling with coworkers, while not as tangible as an exciting new idea, is just as important to the long-term success of you and your team. Proper communication is the lifeblood of distributed teams. By spending extended in-person time with coworkers, you’ll be able to accelerate how fast you get to know each other’s habits, interests, strengths, and weaknesses. The productivity gains will be apparent immediately.
There are plenty of opportunities to do awesome things with coworkers, including attending conferences, traveling to exotic locations, or simply visiting them in their hometowns. Doing so frequently and regularly is a great way to enjoy your travels while accelerating your personal and professional growth.
At the beginning of this article, I mentioned that it might seem daunting to try to do everything at once: travel, work full-time, stay healthy, make new friends, and find time to actually enjoy yourself while exploring new places.
It’s important to understand that it’s a balancing act, not a to-do list, and there’s definitely a domino effect. Spending quality time on one thing doesn’t take away from the others; it’s all interrelated. When you’re having a great time traveling, it’s easier to meet compelling people. When you’re spending time learning new skills, it’s easier to be hyper-productive at work and meet people who share the same professional interests.
It’s when you hit that sweet spot that this lifestyle really reaches the next level. Before you know it, you find yourself doing such things as executing high-impact company initiatives from rooftop beachside apartments before taking a lunch break to go jet skiing, or reading data science books between asados with new friends.
The possibilities are endless, and there are always new places to visit and exciting goals to achieve. The world is an amazing place, and I hope everyone gets a chance to see it. Good luck and happy travels!
If you have questions about anything in this post or are just curious to know more, you can reach me at [email protected]