Biggest Challenges for Digital Nomads and How to Overcome Them

Although I’ve worked during my travels on five continents – and actually, some of those travels occurred because of professional obligations – I’ve never considered myself to be a digital nomad.

Why? Digital nomads are folks who live outside of a suitcase or backpack for more than two weeks at a time. No official definition exists, but true to its name, these “wanderers” are doing more than taking exotic business trips or adventure-seeking vacations: they’re living life on the road. And that road may be paved, winding through a jungle, or littered with livestock.

These folks are a different breed altogether whose transience would likely warm Kerouac’s heart.

I spoke with a few about their biggest challenges for digital nomads, and how they’ve found ways to overcome them:

1. Kevin Chau, Marketing Freelancer and Travel Blogger, The Boarding Call

Current location: Hong Kong

A former startup employee, Chau has taken the plunge into full-time freelancing and is sharing his travel knowledge on his blog. He advises others that blurring the lines between one’s work and personal life is an area to approach with caution.

Challenge: Achieving Work-Life Balance

“The biggest challenge I’ve encountered is how to create a work-life balance—which really just ends up turning into a work-life integration. Instead of leaving work at work and home everywhere else, you have to set rules on what occasions it’s okay to briefly check in on work stuff, and when it’s not. Because let’s face it, when work is integral to allowing you to do what you love, there’s no separating it. Having a daily ritual and setting up one specifically for work really helps. I also blocked off parts of my calendar for no work, and used separate apps for work calendar and email. My go-to tools are Airmail, Fantastical, and Harvest.”

2. Duncan Falk, Website Designer and Developer, Design Freund

Current location: Czech Republic

Challenge: Travel is no excuse for work lapses

“Work-wise, to keep up the amazing travel experience it is vital (and challenging) for me not to allow the travel to be an excuse for my work suffering. It is inevitable that a flight will be delayed, or a place will flood, or Internet will not be available; I can’t allow myself to give a client a travel excuse or other reason I can’t deliver. My service cannot suffer because I want to enjoy an amazing personal experience. That requires planning and flexibility, and also accountability so as not to spend my time in another country working totally indoors—ruining my personal experience either.

So there’s a great balance and need for accountability, but it’s all for the better and allows me to make the most of it.”

3. Brooke Hurford, Product Designer, Workfrom

Current location: Costa Rica

Challenge: Missing loved ones back home

“My biggest struggle so far is leaving friends and family back home. I find myself feeling guilty that I’m not around; I can’t be there to watch my niece cheer at basketball games, or watch my nephew start track. To stop by my gramma’s or have family night on Sundays. I plan to keep in touch, have quality phone calls and FaceTimes.

I also plan to send small gifts and cards to make sure they know I’m thinking of them 🙂

…that counts for friends too! And I also plan to have my mom and some friends come meet me.”

4. Pauline Chin, IT Support Contractor

Current location: Germany

Chin has made it a point to attend many programs in order to meet others with a similar lifestyle, including conferences specifically for digital nomads.

Challenge: The journey can feel lonely

“I believe after two years the biggest challenge I face is having to say goodbye to the friends I made in each community. Even if I return to the country, you can never return to that moment in time. The feelings and friendship you developed will change as people move on with their own life. It’s hard to find that community that will grow and change with you. The locals cannot freely move like myself and other nomads move at their own speed.”

Challenge: Your travels must have meaning

“The anticipation of your departure date changes how you interact with people. Psychologically, I noticed that I stopped connecting with people at a deeper level. I started to actively seek out volunteer opportunities. I wanted to give back to the community. You need to provide meaning to your travel in order to sustain this lifestyle.”

5. Melissa Ng, Founder of Melewi

Current location: Switzerland

As a remote company founder, Ng is learning much as she goes—courting clients while on the move and navigating the tricky waters of running a business with a shifting home base.

Challenge: Building friendships and a sense of community

“Constantly bouncing between places means it’s hard to feel like you have a community around you. Over a long period of time, that can make you feel very secluded, but you also start to shy away from making deeper connections with people and friends since you know it won’t be long before you have to say goodbye again for the 258th time.”

Challenge: Having “digital nomad” become your identity

“I distinctly remember the moment I realized people would replace asking ‘How are you?’ with ‘Where are you?’ The questions and connection with you became about your lifestyle, your stories and the places you’ve been to (which, don’t get me wrong, are fun to answer). But at some point, all people would care about was living vicariously through you, not about you. I started to feel like I didn’t exist as a person outside this persona, and that was a terribly hollow feeling. Since then, I’ve intentionally refrained from letting it be the focus of any conversation I’m part of. After all, it’s a lifestyle, not my entire life. I’m a person who also happens to live a nomadic lifestyle, not solely a digital nomad.”

6. Konrad Waliszewski, Founder/CEO of TripScout

Current location: New Zealand

Waliszewski, who has visited 100 countries, believes that the various lifestyle, financial, and productivity benefits of being a digital nomad far outweigh the costs. However, every path has its tradeoffs.

Challenge: Bureaucracy is alive and well

“This may come as a surprise, but processing any official documents can take much more time than you’re accustomed to depending upon where you’re from. Dealing with rare archaic systems can be very frustrating. Some things take way more effort than they should. For example, signing a contract where the other party requires a printed and authentic signature involving a notary or similar official versus just sending a digital version.”

Challenge: Work “routines” change dramatically

“First of all, finding a reliable and quality WiFi connection for calls can be a constant hunt instead of a given. Technology in general can cause headaches: 10 percent of my conversations with my co-founder is asking ‘can you hear me now?’ Because you’re likely in a different timezone from your customers or colleagues, you wind up working odd hours in order to accommodate different time zones. Last but not least, creating a work culture takes a lot more effort; communication needs to be very deliberate, and it’s harder to build relationships.”

While the challenges for digital nomads are plentiful, it’s still a path that many gladly take. If you want to become a digital nomad, check out remote job listings.