The Realities of Digital Nomad Life

This week we are pleased to present a guest post by Stephen Schreck a digital nomad and the brains behind A Backpackers Tale travel blog. He has been wandering the globe to discover other cultures and ways of living for the past four years.

For some people, myself included, the beckoning of the road is too strong to resist. Several years ago, I fled the universe of house mortgages, car payments, and office politics. Determined never to return to the endless grind of a 9-5 career, I took my passions of traveling and writing and forged them into a new online career.

Thus began my journey as a digital nomad. Having traveled through over 30 countries, I have experienced some incredible adventures; from running with the bulls in Spain, celebrating Chinese New Year in a cave house in rural China, and racing from England to Mongolia in a beat up junker. All the while drawing an income online. To some, that might sound almost unbelievable.

However, I am not alone. There are thousands of nomads doing various jobs online while bouncing around the globe having unforgettable experiences.

Traveling the world for a living is incredible. Many mornings I wake up in a new part of the world, sip my coffee, and gaze out at a new horizon waiting to be explored, completely content with life. But, like any other career choice, there are struggles.  I spent some time, recently, talking with other digital nomads about the difficulties of a lifestyle that demands as much as it rewards.

Personal Struggles of Being a Digital Nomad

Before we dive into the untold truths of being a digital nomad, it is important that we all have the same understanding of what a digital nomad is.

Jodi Ettenberg from Legal Nomads  puts it this way:

“The term ‘digital nomad’ is a popular one these days, referring to people who work online where their chosen work allows them to do so from anywhere. I am not a huge fan of how ubiquitous it has become, and as with anything, it has its dark sides. Barring a new term that emerges from changes to the job market, it remains the most apt label for people who want to live flexibly as self-starters while exploring the world.”

Working online and living in foreign countries is not always easy. It is a job that comes with a mess of problems and frustrations. Honestly, at certain points, I have almost given up. I have been burnt out, tired, discouraged, and lonely. At times, the sacrifices seemed to outweighed the rewards.

Relationships Are Temporary

Entering a community of nomads means that saying goodbye to friends, and peers is a common part of life. Friends come and go, and you don’t know how long it will be until you see them again.  Dating is virtually impossible unless you are ready to plant roots in the same place for a few months.

Here is what a couple of long-term digital nomads had to say on the subject of relationships:

“The biggest downside to being a digital nomad is having a bit too much freedom and independence. I’ve been to more goodbye dinners than birthdays as people are always coming and going.” —Johnny Fd

“You’re constantly resetting your friends circle, so you need always to be meeting new people.”  Derek

“Relationships can be tough if you don’t both have the same vision, goals, and drives… but this goes in any relation. The difference is the ‘location independence’ of the digital nomad – it must be something you either both share or can bear the time apart. I’ve been fortunate to be surrounded both by friends and loved ones who shared my passion for travel and the world.”  –Ian Ord, Where Sidewalks End

Business is Constantly Changing

Everything is always changing when you live life as a nomad, sometimes, even how you make an income.  The internet is a fickle bed partner and constantly needs monitoring.  I am always testing my strategies to make sure they are working, researching to stay current on the latest trends, networking and nuturing multiple connections.

Big companies like Facebook or Google own us. One new update can totally change a way we run our business, or even worse, destroy a strategy that had been working for years. The internet runs our lives, and we have to play by its rules.  The worry is that, at the drop of a hat, I could lose all my search rankings and, just like that, lose my outreach to the community I have spent three-plus years building.

Because of this, many of us have numerous projects constantly on the go, learning new things to create multiple streams of online revenue for safety. The thinking is that if one way of business disappears tomorrow, another one will pick up the slack.

“Be grateful for whatever you have. Be confident in man’s ability to adapt to any situation. Be prepared to wake up tomorrow having lost everything, and you’ll have one up on fear.”   –Dino, Wonder Kids English

Loss, Loneliness & Starting Over

A nomadic lifestyle is one of constant loss, long stints of loneliness, and always starting anew. After a while, it can take an enormous toll on you. Personally, my second year on the road was rough. I was sick of meeting people for three days, and I started to feel as if no one really knew me.

Where traveling usually makes people more social, when doing it for a living, it can sometimes have the opposite effect. I found myself more comfortable alone in my bubble. I often found myself focusing on work, not because of deadlines, but because I couldn’t stand any more goodbyes.

Now, I travel much more slowly and put energy into making real friendships. Sure, I still have to say goodbye, but the friendships I make now are deep and lasting. Although the miles frequently divide us, I find myself meeting up with these people over and over again.

Travel Burnout

Balancing work while traveling full-time truly messes with peoples minds and, if we are not careful, we can end up feeling drained, depressed, or eventually despise traveling. The things that were once new and exciting, like the buzz of an airport, staring in awe at a towering temple, exploring vast landscapes, or feeling the electricity of a new city, lose luster with time.  Activities that were once loved, almost become a chore, and it is easy to lose that vision of why you chose this life in the first place.

Moving all the time can also become a hassle. Every few days, weeks, or months, I reroute my entire life.  This includes planning, researching, and manipulating hundreds of pieces of the itinerary puzzle.

Tangible things like creating our own personal space, buying a pet, or owning a home are almost always out of the question.

“Dealing with logistical things can be a hassle – finding a new apartment, motorbike, etc. every couple months.” –Derek

Losing Time With Family

Digital nomads sacrifice precious time with their loved ones; something that weighs heavily on me. As I am often out of the country 99% of the time, I am lucky to see my family once a year. The older I get, the more I realize that time passes quickly, pushing me to find new ways to share my life with them.

Myths vs. Realities

More than a few misconceptions shadow the reality of what it really means to be a digital nomad.  Let’s debunk some of them.

You’re a Genius, or a Tech Guru

Many people think being a digital nomad takes a certain set of skills, or the expertise of a tech guru. However, many of us know people that are not either, but who have still found a niche, allowing them to to make money online.

Anyone willing to learn is capable of starting projects and developing an income online.

  “A lot of folks think that becoming a digital nomad is far outside their reach. The truth is, however, that we’re now at the beginning of a significant shift to location independent “work styles.” The time is ripe for those with ambition and creativity to carve their own paths.” –Dino, Wonder Kids English

Anyone who has a little ambition, and a desire to learn, while striving to tap into their creativity has the potential to become a digital nomad.

Living On The Road is No Work & All Play

One of the most prevalent myths is that this lifestyle is all play and no work. Oh, if only that was the case.  The truth is, that most of us work more than 40 hours a week because the internet is an incredibly competitive place.  The upside is that we don’t report to anyone and we get to pick and choose the projects that we are working on.

“I like the quote by Lori Greiner – that entrepreneurs are willing to work 80 hours a week to avoid working 40 hours for someone else – that’s also true for digital nomads! The reality of working as a digital nomad is you spend most of the time in an air con room, fighting the wifi, and trying to get work done while your buddies are off island hopping or surfing! It’s totally worth it though!” –Chris Stevens,  Epic Gap Year

Digital nomads are all driven people, and like what they do, so, they are always starting new projects, investigating new paths, technologies, opportunities, and working on building and enlarging their business.

“Most of the time I put in a full workday, five days a week, just like everyone else.  The difference is I have the freedom to do it from anywhere in the world and at my leisure…. and take a lot more vacations.” — Johnny Fd

“In the beginning, the biggest struggle was balancing work with play. Starting off I would spend the majority of my waking hours either working on projects and problems or thinking about them. It’s vital to make time each and every day for activities that are non-work related and require focus.” — Ian  Where Sidewalks End

Having a Life On The Road is Luck

“You’re so lucky,” is a phrase many digital nomads hear almost weekly. For many of us, hearing this phrase over, and over, causes our blood pressure to instantly rise.

If you noticed one common theme in this article, it is how much effort, planning, and problem solving on a daily basis, go into living this life.  Calling it luck implies that it all just magically happened one day. Don’t ignore all of the hard work, sacrifice, and dedication that go into making thd dream of a digital nomad lifestyle a reality.

Many people try to take this path only to quit at the first sign of trouble. More than a few individuals have become discouraged and have given up after the first failure that cost them money, not realizing that they were on the brink of making it.

Successful digital nomads tend to be stubborn, diligent, and determined; having the willingness to go a little further, and sacrifice just a bit more. Flourishing digital nomads aren’t lucky; they are driven.

Tools, Strategies, Logistics & Drive

Digital nomads build electronic empires using tiny devices. What is terrifying about this is that electronics fail. Personally, I lost a couple years of travel photos stored on two hard drives when they both decided to quit working within a week of each other. Needless to say, backing up my work and having copies and multiple components in place is vital to this way of living and working.

In fact, I keep backups of backups on two separate external hard drives and vital data backed up twice more on thumb drives, along with everything backed up on two separate cloud services.  Tools like Google, Dropbox, the Cloud, and external hard drives, all become lifelines to the digital nomad.

“I backup everything on the cloud at Google Drive, including all of my podcast episodes, websites, photos and files. The best thing about having everything in the cloud is being able to access it from anywhere, and being able to get back to business within minutes even if you lose everything.” — Johnny Fd

“Dropbox. I operate from my dropbox folder. Everything I do is automatically backed up, so even if my laptop breaks or gets stolen, I can download my entire workload to a new computer in a matter of hours. I’ve had to do this twice, and Dropbox was a lifesaver.”– Derek

Strategies of Digital Nomads

Continually developing new and fresh strategies can be overwhelming. The internet is endlessly changing, updating, and adapting to consumers. Here are some winning strategies from some successful digital nomads:

“Staying true to core values and vision. Sometimes this is hard for a lot of small businesses when opportunities knock on your door offering fame and fortunes – but building a business, you can be proud of means sticking to your own personal core values from the beginning and not straying. For me, that’s definitely about giving back! If it’s to our employees, partners, or projects in the areas we operate – anything you can give back (time or money) goes a long way. “–Ian , Where Sidewalks End

“Learn how to live below your means and try to have enough of a financial buffer to last you 6 months so you know you can take your time to build a proper business and not run out of money and stress out.”–Johnny FD

“Travel slow, keep a visual checklist of tasks (I carry around a mini white board or turn hotel mirrors into my notepad!) and keep your eye on the goal.”–  Chris Stevens – Epic Gap Year

“Set easy to achieve goals to strengthen your confidence and determination. Look to those around you and online for advice and support. There are a lot of people out there on a similar path who would be happy to pass on a lesson they had learnt. Reflect on your work and experiences each day. Did you accomplish something significant? Was today better than yesterday? How will tomorrow be better than today? Travel slow and take the time to meet locals wherever you are. Learn the customs, speak the language, and experience the culture.” – Dino: Wonder Kids English


Logistics are another tricky part of living and working on the road. Often you are dealing with clients on the other side of the planet. When you are waking up, they are already having dinner with their families or sleeping. Waking up at three thirty in the morning to have a 30-minute meeting sucks. Even worse, is the client with pressing issues who reschedules at the last minute.

One way digital nomads deal with this problem is by basing themselves in an area where the difficult logistics can be minimized, or managed. There are hubs all over the globe in the every time zone for people working online.

“If you’re doing client work and need to schedule phone time, time zones can be difficult. That said, there are a lot of great digital nomad locations in all time zones – for instance, Colombia, Panama, or Costa Rica are all in the same time zone as the U.S.” –Derek

Working online frees our hands in the sense that we can live where we please, work when we want, and on the projects we wish. However, sometimes, this freedom also binds us.

For example: a couple of months ago I was in China, just a few towns away from some amazing mountain hikes that had been on my bucket list for years.

However, I had upcoming deadlines. Even in large cities, the wifi in China is terrible, and I knew if I went to the mountains, there would be no chance of finding an internet connection good enough to meet my deadlines.

This not only meant a loss of income but also the possibility of losing a long-term contract. There I was, right next to a dream of mine, but instead of my having my bucket list adventure, I had to look at it from a train window as I headed back to Beijing to find reliable internet.

“Certain travel experiences are harder to do as a digital nomad. For instance, going into the rainforest for two weeks without WiFi is virtually impossible. So we do need to stay in WiFi range.” Derek

Logistics can be tricky, and you often have to sacrifice pleasure for work. Sometimes that means returning to the same place over and over again.

“I definitely travel slower now that I work online, and I tend to book better accommodations – both for privacy to work and better wifi! I also tend to head to a lot of places I’ve already visited before – I know the setup but also, I’m less distracted by wanting to explore as much! Don’t get me wrong I still have awesome travel experiences, but at the end of the day I need to make sure I have a steady income more than I need to go on another snorkeling trip! Surf will always come first though!”  –Chris, Epic Gap Year

“Even though I travel to seven or more countries a year on average, I try to stay in each of them for long enough to settle in,  find a good coworking space and develop a stable work routine.

My favorite thing about coworking spaces is the fact that everything’s taken care of including meeting other digital nomads and socializing which allows me to plug straight into a new country and get to work.”– Johnny Fd

Tool Kit

A toolkit is also another essential part of this lifestyle. However, the toolkit I carry isn’t quite like what you would expect.  Basically, I have to carry my office on my back. What does a digital nomad toolkit look like?

“Besides my laptop, I need a pair of earbuds with a mic, a couple external hard drives, and a cup of fresh coffee to complete my work.” –Dino, Wonder Kids English

“My office is pretty light – Macbook Pro, 3 external hard drives, and an iPhone. Pretty much all essential!” –Chris Stevens,  Epic Gap Year

“My everyday carry consists of a 13″ Macbook Air, a Roost Laptop stand with a wireless keyboard and mouse. Other than that, I also carry a nice set of headphones, and a quality microphone to interview entrepreneurs that I might meet while traveling or at a coworking space.” —Johnny Fd

“I wouldn’t be able to do my job without a stable, fast internet connection, or my laptop, but aside from that, being a digital nomad requires a lot less equipment than most jobs back in the “real world.”–Derek


Being a digital nomad is a rewarding lifestyle, but one that has challenges as well.

One on hand, there is the freedom to explore the world, to live and work anywhere.  On the other hand, the struggles include:

  • Balancing relationships
  • Managing fluid business landscapes
  • Coping with loss, loneliness & starting over
  • Travel Burnout
  • Settling into the realities beyond the myths
  • Developing the tools, strategy & drive to be successful over the long term

Life as a digital nomad is busy, complicated, and uncertain. Parts of it are fantastic, but it is still life, and life is full of hardships and trials. If you are willing to pay the price, it is a career adventure like no other.

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