After paying your corporate dues for years, you’ve made the exciting decision to kiss your cubicle goodbye in exchange for a workspace that looks more like a Corona commercial. And you’ve done your homework! You already know all about the best credit cards for long-term remote workers, the cities with thriving location-independent professional communities, and just how easily your home country’s passport will make traveling. Heck, you’ve even taken an online quiz (or two) on the topic of where to begin your remote life.
But all of the preparation in the world can’t prepare you for the realities of life on the international road. The work-from-anywhere life, I’m afraid, has to be lived to really get the hang of it. But we’ve got the next best thing: eight recent digital nomads who have taken the plunge, and share the daily challenges and pieces of sage wisdom that come from personal experience. So you think you can work from anywhere? Brace yourself for a whole new set of hurdles in your new “free” life.
The “working from” is often less important than the “working during.”
So you’ve decided to take your professional dog and pony show on the road, huh? Congratulations! Expat remote workers abound in far-off places like Prague and Thailand. But while many are able to successfully untether themselves from work’s geographic limitations, breaking free of the time zones your colleagues and clients live and work within can prove to be much more challenging.
Richard Hessler, a member of a small pre-Alpha team at Patron, says:
“Some remote workers may need to adhere to Daylight Savings and others not, but like most people trying to integrate to the late-sleeping/late-rising lifestyle of Latin America, it has completely ruined my sleep/work life balance. Meeting times back in the physical office have, on more than one occasion, been miscommunicated because of the five times zones ranging from Pacific Standard Time to Central European Time that our team resides within. It’s challenging to say the least.”
Figuring out how working from a new place works takes time.
Like eternal snow bunnies in search of fresh powder all year long, or professional surfers chasing the summer from hemisphere to hemisphere, so too does a specific breed of remote worker get the heck out of Dodge just as soon as it begins to feel like home.
And while companies like NomadList exist to help nudge aspiring remotes toward global destinations possessing both the physical infrastructure (think high-speed Internet service, a financial system with favorable exchange rates for U.S. citizens, a housing market open to short-term apartment rentals) and a community of like-minded digital natives, the physical act of settling into your new hometown takes energy and time.
Miranda Weston, a Pittsburgh-based operations director for startup SEWNR, says getting the feel for your new temporary hometown can be potentially rife with social and technological anxieties.
“I think for me, the hardest thing is knowing what works for you. Some people can thrive in a co-working space and others need to work alone or in a coffee shop. Even though I have been a remote worker for a while now, it is still a struggle each time when I get to a new destination and have to spend the first few days finding a place that can serve as my work space — whatever that may be. With each new city, familiar questions abound. Where can you get Wi-Fi? And where is it appropriate to have a computer out on the table? Even now, it’s something I am still working on.”
There will be hunger pains.
While you might think that aligning your wayward remote time zones to New York or L.A. business hours will prove to be the most challenging clock-related issues you’ll face, culturaltiming troubles will also abound.
Charles Du, an ex-rocket scientist turned entrepreneur currently based out of Argentina, warns that stateside mealtime habits might not necessarily align with the dining cultures of your new host nations, particularly in Europe and Latin America.
“It’s impossible to find food in parts of Argentina between 5 and 8 p.m. People here normally eat dinner after 9 p.m., and it’s taking me a bit to adjust to being a hungry nomad.”
The drudges of office life abroad are no less soul-crushing.
For those whose professions allow them to work abroad at least in theory, but require significant workspace infrastructure, coworking offices may appear to be an attractive option. But the reality of working from an office in an exotic foreign country still feels an awful lot like working from an office.
David Baum, a newly nomadic account executive with the San Francisco-based Strategy firm The Siren Agency, lifts the rose-colored glasses.
“Working while traveling the world, hopping to numerous countries! The thought of feeling stale or lackluster seems impossible, right? But I’ve found that cooping myself in a workspace for eight hours a day in a foreign country invokes the same upwelling of banality that it does in the states.”
Be prepared to surrender your power.
Lindsay Orr, a New York-based sales development representative at Parse.ly, says that even when you’re fortunate enough to work for a company that is incredibly supportive of extended remote work, challenges may still arise.
“Luckily for me, Parse.ly’s entire product team is distributed so the company is set up to make working from home (sometimes permanently) possible for everyone. But being physically separated from our social, fun crowd has also removed me from a portion of the decision making. But there’s nothing I can do about it, except reposition my focus and work more independently in my role than I’m used to.”
American benefit packages and international infrastructure don’t necessarily mesh.
So your U.S.-based employer offers a generous health insurance package? Good luck taking advantage of it while working from a foreign country. Likewise, company gym memberships, public transportation subsidies and catered lunches may be accounted for in your salary, even as you no longer have access to them. Even a simple case of stomach flu comes with complications. Chicago-based graphic designer Jonathan Black shares his story:
“While working from South America, I came down with a bunch of flu-like symptoms after only a week and a half of travel. Should I use my valuable sick days, or work through the struggle of barely being able to get out of bed? I was warned to be wary of hospitals in certain cities, as their practices may not be deemed as safe as those in the states. I played with every possible scenario of what my diagnosis was. Do I have food poisoning? Common flu? DENGUE FEVER?”
Black emerged unscathed, but says when you’re sick in a remote situation, “be transparent with your team, and sleep as much as you can.”
Not everyone (or every employer) is going to like your new remote situation.
When Los Angeles-based design strategist Derrick Sun informed his boss at a free-spirited global technology company of his intention to work from the international road for an extended period of time, he was surprised to learn that the news wasn’t exactly welcomed with open arms. Upon learning his request to go remote was denied, Derrick says:
“Although I thought the organization’s policies might be more lenient toward flexible working styles, I decided in the end to leave my job to travel the world as a freelancer. As the professional climate evolves, it’s my guess that companies that cannot embrace flexible working styles or trust their employees to be simultaneously accountable for their work while living in far-flung parts of the world may have trouble with employee retention down the road.”
Be prepared to make your case, over and over (and over) again.
For those who opt to walk the remote plank, explaining your situation and defending your value to the company will become a recurring theme. Your current direct manager’s approval of your time away from home comes with zero guarantee that she will remain your futuredirect manager. Remote workers must always keep in mind that companies are constantly evolving organisms all their own, and that with every new hire, fire or promotion back in the office may come the necessity of explaining yourself all over again.
Marina Lvova, who works remotely for a New York advertising technology company, says expanding your responsibilities to meet the gaps back at home is critical to your extended employment while abroad.
“Flexibility and positivity are key. What can you do differently to take on necessary work? What do you bring that no one else can? In my case, it is institutional knowledge and a desire to work cross-functionally beyond my current day-to-day. This might mean training across departments, project management, or owning work beyond my ‘scope’. And speaking of scope, you may have to redefine your idea of the word.”