The Dark Side of the Digital Nomad

Traveling the world while making a living as a digital nomad is an experience like no other, but there’s another side of it you don’t often hear about.

The following is the original piece I wrote for CNN last year about location independent entrepreneurs, also known as “digital nomads.”

Since the whole “Work Online, Travel the World and Live the Dream” angle had been done to death in a million places, I decided to go the other direction and show the dark side of being a digital nomad — the challenges one faces, the emotional pitfalls, the social sacrifices.

Predictably, CNN hated it. The editors hacked it to pieces and asked me to rewrite sections to make it less gloomy. And since they’re CNN and I’m just an asshole with a book about smut, I said OK.

But I was always fond of the original, so I’m posting it here unabridged. Also note: the people and events in the piece are actually composites and mash-ups of my real life experiences and relationships. I did that for the sake of narrative and space. Enjoy.

It’s 12:20PM on a Friday afternoon when most of them shuffle into the hotel conference room. The schedule said 11AM. Wishful thinking.

Floor-to-ceiling windows look out over a rooftop lagoon with the sunny reflective skyline of Bangkok draped behind, 19 floors up.

The people’s feet are adorned with flip-flops and Converse sneakers, some of their bodies in button-downs and blazers, others in cargo shorts and tank tops. They are mostly men, single, in their 20’s and 30’s. But as with every group, there are the exceptions. Eventually 44 of them will fill the full-windowed conference room, bathed in natural light, sipping Singha beer and thirty-cent Red Bulls, listening to ad hoc presentations about outsourcing, systems management, dropshipping, grey-hat SEO, and other esoteric topics.

Unless someone told you, you would never guess that this was a conference for successful internet entrepreneurs and business owners from around the world, that the median income of the scraggly-faced, wrinkle-shirted crowd is likely well into the six-figures. And many of them make most of it while sleeping off their Tuesday night hangovers.

Spontaneous international congregations like this are quickly becoming the norm as more and more entrepreneurs remove themselves from the grid and choose to live nomadically.

In his book The Four Hour Work Week, Tim Ferriss dubbed us the “New Rich”. The idea is we leverage the internet to scale and automate businesses quickly, and then we leverage our location independence to create a greater wealth of experiences through travel and adventure rather than collecting material possessions.

For a group of people spread all over the planet, the New Rich paradoxically run into each other quite often. We’re highly networked online and we all have a penchant for landing in the same handful of locations.

There are the start-up incubators: groups of green internet entrepreneurs who come together in an affordable location to live together and help each get their projects off the ground. Southeast Asia is ground-zero for many of these incubators due to the rock-bottom cost of living and high quality of life: Chiang Mai and Bangkok in Thailand, Saigon in Vietnam, Bali in Indonesia, Cebu in the Philippines and also more recently Medellin in Colombia.

Then there are the entrepreneurs bent on cashing in on emerging markets – countries and cultures which are maybe 5-10 years behind the curve in terms of internet sophistication and market saturation – ambitious Western entrepreneurs swoop in to take advantage of the opportunities in places like Buenos Aires, Sao Paulo, Beijing, and Kiev.

Then there are the conferences, the meet-ups and the masterminds, a smattering of which are organized across the world in places like Las Vegas, Berlin, Tokyo, Miami and now Bangkok.

The social life of the New Rich is bizarre. The line between business networking and friendship is non-existent, as the handfuls of people on the planet who can relate to your lifestyle also happen to be possible joint venture partners and/or clients. Conversation and support is always a blur of intentions.

The other strange aspect of this lifestyle is that the people who you are most connected to and relate to the most, you only see a few times a year. The last time I saw my best friend (who is location-independent as well) was last December in Guatemala. And before that I saw him in Singapore in October. Before that he visited me in Thailand in August.

But there are some friends who you never actually see.

Sitting at the table with me is Jay. I attended one of Jay’s webinars a few months prior and recently hosted him on one of my site’s podcasts. He also briefly lived in Bali with an SEO expert I was friends with in Colombia. Despite “knowing” Jay for six-plus months and strategizing about our businesses regularly, I have never met him until today.

Also with us is Tom. Tom is American and a top-dollar online business consultant who lives in the Philippines and is now mentoring one of my friends back home in Boston. Tom and I and half a dozen other entrepreneurs are members of a mastermind group that hold weekly hour-long calls together where we discuss our businesses and our lives. Despite speaking to Tom weekly for the better part of a year and asking and answering each other many personal questions, this is the first time I have met him in the flesh.

And yet this feels normal now. It doesn’t occur to any of us that almost none of us actually know each other. We run in the same private forums and are members of the same email lists. We all know someone who knows someone who knows someone. And we’ve all cut our teeth building our businesses while living in the same half dozen or so places around the world. Yet we don’t know each other.

We can relate on a deeply experiential level. In a lifestyle where none of our friends or families back home can comprehend what our day-to-day is like, these loose global networks exist for us to keep each other sane.

Yet, for our philosophical connections, we lack that emotional depth and bond that comes with shared struggle and life’s important moments. Mainly because there are few struggles and when the important moments happen, we’re always somewhere else.

The Two Sides of the Digital Nomad Life

One successful entrepreneur, in a rare moment of vulnerability, recently wrote that he burst into tears in a small suburb in Japan watching families ride their bikes together in a park. It struck him that this simple, mundane pleasure was something he would never know again. On my annual short visit home for the holidays, my mom asked me with disappointment in her voice, “Am I ever going to see you for more than a few days each year again?” I didn’t have a good answer for her.

The nomadic lifestyle seems to bolster some egos and bruise others. I credit it with building my confidence and self-esteem. Looking back, I was obsessive and desperate with my habits and relationships back home. Being put in country after country where nobody knew me and nobody cared who I was did me a lot of good. I let go of a lot of baggage.

But for others, it’s the opposite. There are plenty of vices one can freely indulge in in the world, especially in developing countries. And when you’re constantly the center of attention for everything you do and every choice you make, one can fall into a quiet narcissism without even realizing it. I’ve seen it. And it sucks. Or as another nomadic friend recently said, “Some people are better off without this lifestyle. It’s too easy to disconnect. It’s too easy to obsess about yourself. I’ve lost a few friends to it.”

To many back home, we are living the dream. We have access to an unspeakable freedom of choice and boundless personal opportunity. There are few limits. Last year I visited 17 countries. This year I will visit 10. Last year, I saw the Taj Mahal, the Great Wall of China and Machu Piccu in a span of three months. I hiked a volcano and a glacier 2,000 miles apart in the same week.

But I did this all alone. Just me and sometimes a few anonymous faces – acquaintances of mutual travel convenience. My life is awesome – no, really, my life is fucking awesome. It just needs a parental advisory sticker. Because the price of overwhelming freedom is often my isolation.

Back in the conference room in Bangkok, new contacts are made, business ideas are born, and online connections are materialized. A series of agreements to meet up and hang out are made – a pair who will be in Barcelona around the same time agree to email each other; a sub-group mulls over meeting in Berlin next Spring.

For a group of people who all fight the silent battle of loneliness, we sure are fickle with each other. But when you have so many opportunities before you, it’s easy to avoid commitment, even to a friendship. Many of the people and places become interchangeable and you begin to wonder if that’s just because of the traveling or if that’s all human relationships and you just never noticed it before.

Don’t get me wrong. I’m not complaining. I’ve loved every minute of this lifestyle. But there are real, tangible, social and emotional tradeoffs involved. I wouldn’t trade it all for the world because I already did trade it all for the world. Because the world is a pretty badass place. For a while.

Economists say there is no such thing as a free lunch. I say there’s no such thing as a free life. Some of us just learn to choose better shackles than others.

I look back to the skyline, past my Singha-swilling contemporaries. It occurs to me that the New Rich, for all of our impressive values, are just as guilty of materialism as the old rich, it just takes a different form. Instead of an addiction to status and possessions, we are addicted to experience and novelty. And the end result is the same. Our relationships, our connections to what’s real, sometimes suffer. And for the first time in three years of non-stop travel, I quietly wish for a home.

The Digital Nomad Lifestyle

A Digital Nomad – sounds fancy! Right? Well, it’s definitely a fancy word to use for a freelancer. The digital nomad lifestyle implies that you can mix travel with work and clock in from anywhere in the world. Nowadays a hashtag trending on Instagram #DigitalNomad with the pictures of people work on their laptops in beautiful serene places.

For some, a year of travel and freedom just isn’t enough. These people want to spend their lives exploring the world while working when and where they want to and making their passion, their work.

It’s not just a wistful want, where they talk about it, spout travel quotes, read 4-hour Workweek and then come back off their lunch hour to be in free space. They’ve used their skills, qualifications, and passions to engineer their life to suit them.

For them, it’s not about getting a job and living life around that like everyone else. Its living life and creating or finding a job to fit them they are called “Digital Nomads“.

Living As A Digital Nomad

There are WordPress developers, Start-up directors, Amazon shop owners, UX Designers, Inventors, Travel Bloggers and no doubt another few hundred trades. All with different skillsets, interests, stories, and life histories but all with the same passion for somehow making their life pan out differently from the School-Uni-Work / 9-5 society.

As digital nomads, they can combine their work and indulge in their hobbies, spare time interests too. Some locate themselves in destinations specifically for surfing, for kitesurfing, for the beaches, the sun, the city, the festivals, the lifestyle, the culture- wherever it is that allows them to work alongside their idea of fun.

Sounds like a pretty sweet life, But it’s not that easy how its sounds. To be a digital nomad you need endless self-motivation. There is no one to check whether you were in at work at the right time, or how long it took you to finish your lunch. You do the work because you want to. For some, you need to be able to adapt quickly to change and try to stay one step ahead of your peers. You need to understand when to work as a team, and when not; you need to know when to roll with an idea, and when to realize you really don’t know what you are talking about.

If you want to be a digital nomad who works for yourself I’d also recommend you have the wheels in motion before you leave your current job or education. If you don’t, try to find a job that will enable you to work remotely, or even spot a gap and create one in your current company.

It’s not a good idea to leave security to become a digital nomad. You need to have another skill, trade, idea or income source to make the digital nomad part the lifestyle rather than the focus.

Digital Nomads Tips

Becoming a digital nomad is not an easy transition by any means. It’s a lot of work; don’t believe otherwise. No one is telling you what to do it- you have complete freedom to manage your time. This can work in your favor or against you.

Some days you wake up feeling super motivated and smash out a lot of work. Other days you lounge about in your apartment, avoiding working at all costs and telling yourself you can make up for the lost time tomorrow. The only problem with this is if you don’t stay on top of things you will quickly run out of money.

If you dread waking up on a Monday knowing you have another full week of working at a job you hate, then honestly, why work there? Maybe you feel that you are in this cycle of having to work in order to pay for your student loan, apartment, car, and general lifestyle. But instead of saving money or time to do this, then read on for the basic step to becoming a digital nomad.

If you have ever had thought of quitting your job and traveling but couldn’t because you didn’t have enough money or time to do it, then read on for the basic step to becoming a digital nomad.

Firstly start saving your money. Figure out how long you think you’d like to invest in becoming a digital nomad. Start budgeting where your money really goes every month, and save as much as you can.

While you are saving, do some serious research on where you’d like to travel. Start with the Nomad list. It’s a useful site I use from time to time when trying to figure out where to go next. This website provides you with a list of the best cities to live and work in as a nomad. It covers the overall costs of living, Internet speeds, weather, how many nomads are currently there, etc.

Buy a plane ticket. if you really are committed to trying out this lifestyle then just go for it, pack your bag and don’t overthink it. The rest will fall into place. If you are really passionate about working online then you will find something, so just pick a place that ticks all your boxes and go for it.

Think about what you’d like to do abroad. How would you like to make an income? Find something you might be interested in. Or maybe you already have skills such as Android development, editing, designing, or even working as a personal assistant. Play around with ideas and brainstorm a few you may like to peruse abroad.

Minimalize your possessions. If you really want to go the digital nomad route, then you won’t need your possessions at home, like your car, tv, etc. Sell what you can and put the rest in storage.

Once you have completed the above, then it will eventually be time to leave your company. If you have the possibility of taking your current job abroad, then ask your boss.

Before you head out, make sure you have the necessary electronics with you. You will be spending 90% of your time on the computer, so invest in a new one if need be, and make sure you have adequate chargers, USB, etc.

Remember it takes time, don’t be deterred by being the new guy; each digital nomad started at the same place you are in right now. It may seem like are not making any money, or are not good at what you are doing, but don’t let this bring you down. Nothing is going to happen overnight; the biggest thing is for you to keep going, even when things seem hopeless.

Digital Nomad Jobs

Finding a digital nomad job might seem impossible to some people. Maybe you think that only the “chosen ones” get to work and enjoy getting to know new places at the same time.

However, if you are determined and know where to look for remote jobs, it’s definitely feasible and even surprisingly easy for some people.

The list of profession jobs that can be done remotely and therefore are compatible with the digital nomad lifestyle is getting bigger and bigger every year, which is a definite advantage for everyone who wants to try it out.

Digital Nomad Jobs/ Professions that can be done remotely:-

Can’t figure out what to do remotely while living like a true digital nomad? Hopefully, the next section of this article will help you find something that you are good at, enjoy doing and can do remotely.

Copywriting and writing
As you can imagine, a freelance copywriter can communicate with clients online, therefore, work basically from anywhere, as long there is an active Internet connection.
If you think you can write well, be sure to try it out. And if you don’t want to create only marketing texts, feel free to branch out of copywriting to general writing that can cover an endless spectrum of topics and style, as long as you find the right customers.

Taking Online Surveys
Another very easy way how to start your digital nomad life, On websites, you can get paid for sharing your opinions and testing various products or projects to help brands with their customer research.
All you need is to register and build-up your profile. Once it’s done you gonna start receiving surveys that match your knowledge, hobbies or products & services you usually use.

Social Media Manager
Big companies have their own social media managers or hire online marketing agencies to manage their social media.
However smaller companies often hire freelance social media managers that take care of their accounts and help them grow.

Affiliate Marketing
This is technically not a job, but it’s something that can make you location independent. Start your own websites or blog and promote other people’s products or services that you believe in. You will receive a percentage of sales made to people that came to their websites through your affiliate link.

Illustrating and graphic design
Have you always been good at drawing? Maybe it’s time to turn your skill into a career. Use social media to promote your work or previous drawings and you might find some commissioned work that will mark the beginning of your freelance career.

Programmers can work remotely too! There are countless remote programming jobs opening every day. There are even websites dedicated specifically to remote programming jobs. If you are a programmer or want to become one it’s a great opportunity to become location independent.

Are you great at writing but don’t want to write for other people? Write for yourself! Create a blog and write about stuff you care about. Who knows, it might become a career one day, making you able to become a digital nomad. You can blog from anywhere, can’t you?

Why People Fail In The Digital Nomad Lifestyle?

The digital nomad lifestyle certainly has a lot to conceivably offer. When life is good, it can be exceptional. It’s easy to have a tint of rose color in your sunglasses when you are working from the beach in Bali. What could go wrong?

  • Leaving Without A Plan
    People tend to get really excited when they hear about the great advantage of a “digital nomad” lifestyle. It sounds so easy! Seemly everyone can simply pack their bags, move to a digital nomad hub and everything else will fall into place.
    In the beginning, it might be great to just hang around with like-minded people for a while and relax the day away. But after a few weeks, they realize that they need to generate income somehow. But it is not as easy as they thought it would be. They start to struggle with this lifestyle.
  • Lack Of Funds
    The first reason people failed in the location independent lifestyle is related to money. Without money, there is not much else to discuss.
    So, before you quit your job or buy a plane ticket, make sure you have a steady job or reliable way to fund your life and travels for at least the next 6 months up to a year.
  • Culture Difference and inflexibility
    Few people discuss the considerable energy required to set up a business abroad, or one that can serve your needs across borders, Many digital nomads learn the hard way that their time can be sucked up by paperwork and red tape on the operational side of their business.
    Then there is the personal side of life as an outsider. Some cultural differences that seem endearing while on vacation can become burdensome while living abroad long- term.
  • Loneliness
    While it’s possible to feel lonely even if you are married with kids in a comfortable job with all the boxes of the dream checked, loneliness is one of the most commonly discussed downsides to the digital nomad lifestyle.
    Working alone in advancing your online career or business coupled with living in a foreign country thousands of miles from home can be particularly isolating. Issues concerning loneliness extend to all relationships: friends, family, and partners.
    While it can be easy to meet people while traveling, it can also be hard to say good-bye. The transience of the digital nomad lifestyle is a factor to keep in mind.
  • Leave without enough information
    If you don’t have enough information about this lifestyle, you might end up hating it. Maybe you have expected the wrong things from it. Maybe you thought you can quickly get rich with this lifestyle. But the reality looks different.
    Often people have no idea about the legal part either. They don’t organize a visa in advance when they should. They don’t get working permission when it’s necessary. They don’t get a bank account with good conditions for long-term travelers.

Should I Start a Blog? 8 Good Reasons to Start a Blog in 2020

If you find yourself wondering out loud, “Should I start a blog?” all the time, you probably need to give that inner voice talking to you a chance.

Blogging is one of the quickest and easiest ways to express yourself online. The fact that it’s literally free and has the potential to bring in an income has seen more and more people start blogs every day.

So why should you write a blog too? What is so good about blogging that means everyone should have a go?

You may not know it yet, but there’s a pretty good reason why you’re having that strong desire to start a blog.

Don’t wonder anymore. Here are some pretty good reasons why you should blog.

*This post may contain affiliate links. If you click on them and purchase something we get a small percentage of the sale.

Why Should I Start a Blog? 8 Reasons to Start a Blog

1. Do something you’re passionate about

Most people find themselves blogging because they are passionate about something and they want to share their passion with others.

A blog gives you the platform to do something that you’re passionate about. You probably enjoy cooking more than anything else. You want people to enjoy making food as much as you do. A blog is a good platform to share your cooking skills.

2. To help people

If you’re an expert on particular topics, share your knowledge with others through a blog. You could be pretty good at managing money so teach people how to manage their income.

Putting all your know-how on a blog has the power to educate and help other people. The privilege of helping others in one way or another is one of the most fulfilling aspects of blogging. You rest assured that you are making the world we live in a better place.

3. Travel the world and work from anywhere

Nothing sucks like having a deep desire to travel but you’re only able to do so for two weeks a year. Forget that you’ve worked so hard all year round and deserve a longer break.

Maybe you just want to go visit family and friends who live abroad. But you have to work.

The beauty of a blog is that you’re not bound by geographical boundaries. Because a blog lives online you can take your blog with you anywhere you want. All you need is a laptop and an internet connection and you can go travel the world while still working.

It’s even better if you are making money blogging because you get free time and extra money

4. Anyone can do it

Blogging doesn’t need any specialised skills. While writing skills are important for a blogger, you can keep improving as you go. Getting started is pretty simple even if you have zero technical skills.

Anyone can be a successful blogger as long as they are committed to it, want it badly enough, and are willing to put in the work.

5. Low startup costs

Starting a blog requires very little investment (if any). In most cases, you can get started immediately without spending any money by using free blogging platforms such as and Blogger.

However, if you want to take your blog to the next level you will spend a couple of dollars to buy a domain name, pay for web hosting and maybe a premium template.

6. Build a money-making business

You may be thinking about blogging as a hobby but did you know that hobby can make you money? Yes starting a blog can be financially profitable.

The truth is that not every blog will be profitable. But many bloggers have made lots of money from their blogging, both directly and indirectly.

It takes time, but once you’ve mastered how to get traffic to your blog and have enough readers you will start making some small, passive income. The more traffic you gain the more income you’ll earn. You can actually earn a living from blogging only.

7. Open up new opportunities

A blog allows you to promote yourself as an expert and when people see you as a real expert they’ll want to partner and do business with you.

If you’re blogging because you love writing, a blog could open up other writing opportunities that bring you more income.

If you’re an expert in a certain area, you could create online courses and make passive income from them.

8. Live your ideal life

As a blogger, you are your own boss. This gives you full control of how you live your life. You can easily incorporate work and your hobbies into your daily schedule.

You don’t have to worry about waking up early to commute to work. You can wake up whenever you want and work on your blog whenever you want. This gives you the freedom to do the things that truly matter to you.

We believe these are sufficient reasons to answer the question “should I start a blog?”

Now, do you feel challenged to start a blog as well? If yes, head over to this guide Blogging Blueprint: Zero to Passive Income Step-by-Step and learn how to create a blog on your own!