10 Challenges to Being a Global Digital Nomad

Consider: It's 2 o'clock on a Tuesday afternoon. You have a project due in a few hours and an email from your boss asking how the work is going. Realizing you should pull this whole thing together you slip on a pair of sandals, strut across the beach and unsling your bag at the nearest bar that offers wifi.

In broken Portuguese, you ask for "mais uma cerveja, por favor" ("one more beer, please"), then boot up your laptop and dig in. Welcome to the world of the digital nomad.

At least, welcome to the dream of the digital nomad.

It's no secret that technology has allowed many workers to cut free of their desks and turn "out of the office" from a Friday afternoon treat into a lifestyle. For some, though, working from home isn't good enough. They want "home" to mean just about the whole world, and thanks to tools such as email, Skype and paperless billing, they can do it too.

The digital nomads are an increasingly large band of workers and freelancers alike who've decided that there's no reason they can't have a job and see the world at the same time, but even the best laid plans have a few wrinkles in them. While there are a lot of perks to living and working on the road, this lifestyle comes with plenty of challenges too. Here are the top ten:

10. Working from the Wrong Country
10. Working from the Wrong Country

The key to success as a digital nomad is remembering that this is both a lifestyle and a work-style, but here's the catch: the same thing that defines your nomadic life-and-work-style can also ruin it. When you move around constantly sometimes, you'll end up in places that are really hard to work from.

"I've found it surprisingly easy to work from most countries around the world," said Lauren Juliff, author of the travel blog Never Ending Footsteps, "…places that were difficult to work from are those without great infrastructure: Nepal, where there was often 48 hours without any power during the wet season; Myanmar, where the internet speeds were so slow, I couldn't even download my emails; New Zealand, where free WiFi is still rare in cafes and hostels — I once paid $18 for six hours of internet in a hostel there."

Don't take for granted cities where infrastructure is solid and the WiFi fast, because there are few things more stressful than rolling blackouts in the hours before a deadline.

9. Loneliness
9. Loneliness

"Lack of community" is how Juliff described it.

"You get to meet so many people when you travel the world," she said, "but it's tough to form deep friendships. You're rarely in the same place as someone for more than a few days or weeks, so your life becomes one that revolves around goodbyes. It makes you put up a barrier sometimes, because is it really worth grabbing a coffee with someone when you'll just have to say goodbye a few days later, most likely never to see them again?"

Although people who work from home complain of an epidemic of loneliness, it seems like digital nomads shouldn't have a problem. They're constantly hanging out at guesthouses, hostels and bars after all, right?

Right, and wrong. Moving around constantly means never getting to make real friends, never knowing someone for more than a handful of days. And there are few better ways to stay alone in a crowd than to bury your head in a laptop (like, for example, when you've got a job to do).

Life as a digital nomad involves lots of acquaintances and relatively few friends.

8. Striking a Work/Life Balance
8. Striking a Work/Life Balance

"Living the digital nomad lifestyle is a very attractive way to work," said Brie Reynolds, the senior career specialist with the website Remote.co."But anyone who does it successfully will tell you it takes a lot of planning, problem-solving, and self-management to make it work."

Like loneliness, here digital nomads take an issue well known to every remote worker and turn it up to 11.

Whether you work for yourself or just permanently out of the office, you pretty much take control of your own schedule. Unfortunately, far from pitching your tent in Margaritaville, for most successful professionals this makes it harder and harder to hold on to personal time. There's always one more edit, one more e-mail, another comment or a line of code to debug…

Putting four corners around your workday is tough for remote workers and doubly so for the digital nomad, especially if you work with people in different time zones who will e-mail at all hours of the day and night. It's a must though, otherwise you'll end up a workaholic with a killer view.

7. Travel Disruptions
7. Travel Disruptions

Travel defines life as a digital nomad. That doesn't necessarily mean constant travel, as Juliff pointed out, she often will establish a home base and stay there for a month or more while working on her writing and consulting, but you'll board planes, trains, taxis and boats far more than the average worker.

And every point creates the potential for instability.

As any business traveler can tell, every time you move from Point A to Point B, there's the chance that you'll get there late, later or even never at all. Airlines do cancel flights all the time, and that can mean hours upon hours spent sitting around in an airport. Now multiply that by slower boats and the shaky transport links in many developing countries and you've got a recipe for losing potentially days in transit limbo.

That's frustrating enough on vacation. It can spell disaster in the middle of the work week.

6. Staying Connected to 'Real Life'
6. Staying Connected to 'Real Life'

"The lack of routine that comes from being a digital nomad is usually fine to start with but often becomes a major problem," said Juliff, "because it's hard to find something to ground you. Nothing's constant. You're forever waking up with a different city with a different group of friends — if you have any friends there at all — and eating different foods in a different state of culture shock."

It's one of those things they forget to mention in stories, that however grand your adventure life keeps ticking on both abroad and at home. Friends you left behind grow and get married, families pass milestones and the rest of the world changes. From first loves to retirement parties and everything in between, it's hard to stay connected to all of that.

Email helps, and video chat helps a little bit more, but Facebook is no substitute for holding a friend's hand through heartbreak.

The world is out there. It is every bit as wonderful and weird as they say, but the price for living life "out there" instead of "back here" is steep.

5. Managing paperwork across countries
5. Managing paperwork across countries

"Some of the biggest challenges have to do with the status of the person working," said Brie, "whether the remote worker is an employee or freelancer. Freelancers will find it a bit easier to travel and work without many restrictions because they are inherently self-employed. But for employees who work remotely and like to travel, both they and their companies will need to plan for logistics like their place of residence and amount of time spent working elsewhere because of the tax and employment law implications."

What are your visa restrictions? What are the tax implications of earning your money while sitting in an Indonesian bungalow? Whose law should enforce your contracts, and what will you do if a client doesn't pay?

Do you need permission to work in this country, even remotely?

These are all questions that surround the general topic of "law and paperwork," and for a digital nomad they can be an absolute bear. Every country has a different idea of what constitutes taxable status, not to mention different notions of when you've "worked" in the country, how long they'll let you stay and so much more. Keeping on top of that isn't easy, but it's an absolute must.

4. Keeping a Routine
4. Keeping a Routine

As Juliff noted, keeping a routine is not easy. It's not just the big picture either. To be sure, it's hard to stay grounded through a constant sense of disorientation, but there's also the simple fact of getting things done on a day-to-day basis.

For any remote worker keeping a routine is a virtual must. It builds order into your workday and helps keep you focused and productive. Otherwise it's very easy to fall into the trap of assuming you'll "get to it later" only to realize it's 11:00 pm and you never did.

That's hard enough when Netflix and the refrigerator beckon. When your alternative to work is a hike up Machu Picchu or lao lao shots with the (somehow always marginally employed) global expat crowd, don't expect it to get any easier.

3. Keeping Your Gear Safe
3. Keeping Your Gear Safe

Digital nomads depend on technology. It's in the name.

They also have perhaps the most at-risk gear kit of anyone short of the military or a war correspondent.

Pulling off this lifestyle requires a whole set of expensive equipment. You should generally supplement your (good, flexible) laptop with an ultra-reliable smartphone, some portable hard drives, battery chargers and cables, and that's just the bog-standard kit. You may need another $1,000 worth of gear to do your specific job and all of that is at risk every time you step onto a boat or lock the door to go out for a hike.

Insurance can help you recover the money for any gear that gets lost, damaged or stolen, certainly, but it won't replace your time. Keeping everything safe is a must, and a constant challenge.

2. Reliable Wifi
2. Reliable Wifi

"At a smaller, day-to-day level," Brie said, "digital nomads face challenges like finding reliable high-speed Internet in each of their destinations, finding spaces to work for long stretches where they can be comfortable and productive, managing travel logistics, and maintaining connections with coworkers and colleagues who may live and work many time zones away."

All true, but it's the wifi signal that comes up again and again among people who do this for a living.

Wireless internet is your lifeline. It is how you'll send and receive projects, how you bill, how you check on work and often even how you'll do that work. When the wifi goes out so, too, does your ability to earn a living.

That may be nice from time to time, a little enforced time off never hurt anybody, but that can quickly turn into far too much of a good thing.

1. Balancing Work With Vacation
1. Balancing Work With Vacation

"It has the power to suck the joy out of both travel and work," Juliff said of working as a digital nomad. "It's near-impossible to do both well."

"When you're traveling, you constantly have your mind on work and deadlines and what you need to get done when you return to your laptop; when you're working, you feel guilty for not being outside exploring and taking advantage of the beautiful place you're in," she added. "Everyone I know who's a digital nomad struggles with a work-life balance."

You may not have moved to Margaritaville, but you're not far down the beach.

Perhaps the single biggest challenge to being a digital nomad is finding a way to balance the work-style with the lifestyle. Go too far in one direction and you might as well have stayed home, as all those beautiful sunsets go to waste against the back of a laptop screen. Too far otherwise, and you may find yourself bartending to make ends meet after losing all of your clients.

Making the world work with your work, that's the challenge.