Why Becoming A Digital Nomad Was A Bad Idea

DISCLAIMER: Let me just start by saying I think “Digital Nomad” is perhaps the lamest term on the Internet. I don’t identify as one. In fact, I’d much prefer to be labelled any number of horrible names rather than a digital nomad.

…But alas, in reality it’s probably the easiest way to describe my lifestyle, so I will be using the word in this article.

Hence my self-loathing🍸


I’ve been doing some thinking.

More like some re-thinking.

I’m not sure this digital nomad thing is for me.

You see, it was never my intention to work from the Internet without a permanent residence. But after blowing all of my money on my first trip to Latin America my options were limited. I knew I wanted to go back to the region as soon as possible.

I just didn’t know how.

Initially, my plan was to pick one of the handful of cities I liked, move there and skin by teaching English until I could transition into something better. However, upon researching how little English teachers made in these countries, I was quickly dissuaded. I had already experimented with working online and had made a bit of money, so it didn’t take me long to realize that I’d be much better off freelancing than teaching.

With that in mind, I started directing all my longterm money-making strategies to the Internet.

I didn’t know it at the time, but I was about to unwittingly become a “digital nomad.”


What Happened?

What was meant to be a semi-permanent move to Mexico City did not work out as planned. Upon arriving, I had big dreams. I was going to network, do some freelance journalism, maybe start up an off-the-books business. My online copyediting and copywriting gigs were just meant to keep me afloat while I was hunting for bigger and better things and establishing myself in the city; a means to an end.

But I learned that making money online was no walk in the park. Even in a developing country, I had to hustle hard to make ends meet. Between unsteady and unpredictable workloads, late pay checks and occasionally getting screwed over by clients, figuring out how to break three figures a month was turning into a full-time endeavour.

I soon forgot about my offline goals for the city. In order not to go into debt, I had to focus 100% of my energy on the only things that were actually making me money.

I eventually (sort of) figured things out. I developed a few different online income streams, including this blog, and I was finally able to live comfortably.

But it took a year to get to that point. A point where I was still making much less that what I was earning in an entry-level position in Canada.

Then, something else happened. I began to grow weary of Mexico City. I’d spend a few weeks on and off working from different parts of the country, I popped back up to Canada for awhile, went back to Mexico City and eventually found my way down to Lima, Peru.

Somewhere along the line, I’d adopted the “digital nomad” lifestyle.

I’ve since temporarily left Lima. I’m still working on my online income through this blog, one niche site and freelance work. I’ve also started a service-based website that has the potential to be a massive success or a theatrical failure (like all things, I suppose).

Problem is, I can’t shake the thought that the return on investment for all of this is humorously low.

Countless hours trying to see what sticks for two-figure monthly increases to my bottom line. In the past few years I’ve watched two Internet business ideas of mine crash and burn because I couldn’t figure out how to manage them.

Money and, more importantly, time down the drain.

I would like to say I’ve learned a lot, but I haven’t, really. That tired cliche of “you learn from your failures” isn’t as true as you might think.

I guess I’ve learned that much, at least.

I’ve also learned that if you are attempting to build a life that is 100% location independent, chances are you’re handicapping yourself both personally and professionally.

Here are some of the things I’ve noticed since adopting the digital nomad life.


1. It’s harder to make money

If your criteria for an income source is that it must be location independent, you are shutting yourself off from a plethora of opportunities.


– Forget about any brick and mortar business.

– …Or any business that requires you to keep a lot of stock

– Forget about any job that demands face-to-face interactions, management and/or meetings, conferences…

– Forget about any job where the equipment to do that said job is too big to fit on a plane.


Basically, forget about most things.

Part of the reason I returned to Canada while I was living in Mexico City was because I was offered a high-paying, short-term contract position. But it absolutely required my physical presence in the office. I was able to stroll into that job and earn as much money in one month as this blog makes in six months. And that’s not considering the 100s of hours I put into the site before it earned a dime.

A good friend of mine has a successful construction business in my home city. In three years, he went from earning minimum wage as a labourer to starting his own business and personally earning $150,000 – $200,000 each year. He’s hired the right people and can take vacations anywhere he wants for as long as he wants. At 28 years old, he could be a “nomad” if he chooses.

But he never could have built his business on the road.

It’s important to remember that you can still build a side business on the Internet or work online while having a location-dependent 9-5 job, with benefits. What you can’t do (barring extraordinary circumstances) is have a location-independent 9-5 with benefits.

Staying in one place, in a country where you can legally work and/or establish a business, provides you with many more options and opportunities than floating from one country to the next without the rights and benefits of citizenship.

Keep that in mind.


Have questions?  Skip the guesswork…

Schedule Your Personal Consultation With My Latin Life


2. You won’t maintain personal relationships

I never thought this would be an issue for me.

I’ve always been able to spend days, weeks even, without seeing or talking to anyone and be fine.

Hey, I’d usually be happier that way.

But as I’m getting older and meeting more interesting people, I’m not going to lie: it’s tough leaving people behind. Whether it’s an old friend you’ve known for years, a traveller you’ve known for a month or a girl you’ve known for a night, it’s never easy.

And it never gets any easier.

I often wonder what could have been with some of the women I rejected having a relationship with because I knew I’d be leaving.

Or, potential business and social connections I didn’t foster because my days in their city were numbered. “What’s the point?” I’d say.

And friends. It’s tough to find a good friend these days, no? It’s even more difficult when your constantly moving around. And if you do manage to make friends, good luck staying in touch while you’re thousands of miles away. I love sharing war stories on Facebook and WhatsApp as much as the next guy, but by no means is it a replacement for hanging out in person.

While it’s true that you’ll likely cross paths with more unique and exciting people than you ever would at home, and while it’s true that you never really have to be alone while abroad because it’s remarkably easy to meet people, your interactions will be mostly superficial.

You will not form many deep connections with people as a digital nomad.


3. The novelty wears off…quickly

I thought living in a Latin American country would be the coolest thing ever.

And it was.

For about a month.

After a few weeks, wherever you are becomes like wherever you were. You’ll spend 90% of your time in the same few neighbourhoods, going to the same bars and restaurants with the same people.

Sound familiar?

You’re basically living the same life you would back home, but in a place where the weather, food and language is different.

It’s not necessarily a bad thing – we all need routines after all.

But just know that the endless partying, sex and cultural experiences that you imagined will probably never come to fruition. And the more you try to make it a reality, the more likely you are to fail…and go home broke (I did…and I almost did). If you’re trying to build location independent income, the bulk of your days will be spent in front of your computer. If you’re serious about it, a lot of your nights will be spent there too.

A big reason that digital nomads spend their time in countries like Thailand and Colombia is because they are cheap to live in. There’s lots of sunshine and pretty women in San Diego and Miami too, but they aren’t exactly DM hubs.

(Although I love Latin America for much more than its cost of living, I’m guilty of this too. If money was no object for me, you’d probably be reading a website called “My French Riviera Life” right now).

Point is, you’re not going to have as much spending money or free time as you think. Sure, it makes sense to pick a country you like so you can enjoy its fruits while you’re not working, but don’t think your life is going to look much different than it did in Madison, Wisconsin.


What is Freedom, Really?

Ah, freedom.

The idea that drives the sales of tens of e-books each month for bloggers in the Philippines, allowing them to eat 60 cent Pancit and meet girls.

Find True Freedom! Become a Digital Nomad in 10 Simple Steps.

Or something in that vein.

But what is freedom? In the digital nomad’s case it seems to mean nothing more than to be mobile; to earn money from anywhere in the world.

The irony of this of course is that most digital nomads don’t earn enough money to live in developed countries. They are confined to places where the cost of living doesn’t exceed $2000 a month.

That is the opposite of freedom.

You know who’s pretty free? My friend back home who started that construction business. That dude is gearing up for a one month trip to Australia for the sole purpose of partying and going to electronic music shows. And that’s after he’s just come back from Cancun. He’s got contracts lined up for the next year at least, so all he’s got to worry about is how he’s going to spend the $15,000 he earns each month.

But nobody talks about that kind of freedom and passive income.

Not quite as sexy, I suppose.

It has taken me far too long to learn this.

For many, myself included, being a digital nomad offers a form of escapism; a mode of egress from a unfavourable dating culture in the west, soul-sucking office work or a dire job market. So, we pick up and leave to a places where the women are more receptive, where our dollars will go further and where the culture is unique and stimulating. When everything starts to get familiar again we pick up and leave, resetting the clock, an endless circlejerk in which we convince ourselves that place x will be better than place y.

We mistake a change of environment for progress; we mistake travel for some weird idea of wisdom; we mistake mobility for freedom.

It is sobering to realize that being a digital nomad is little more than chasing the next high, usually at the expense of personal and professional development.

Before embarking on this path, I suggest asking yourself two questions:


1. What’s the end game?

If you want to become nomadic, you must spend time thinking deeply about your motivation for doing so.

If travel is and has always been your number one goal in life and you can’t see that ever changing, perhaps this life is a good longterm fit for you.

Imagine yourself at 40 years old. What will you want? A family? Kids? If so, you will need an address.

It’s OK to do the digital nomad thing for awhile, particularly if you’re scoping out places to relocate to permanently. But have a plan; a template for where you want to be in ten years time.

The wandering nomad is fashionable when you’re in your 20s.

It’s rarely a good look when you’re pushing 50.

Trust me, I’ve met several of the latter.


2. Are there better alternatives for me?

Ask yourself if being a digital nomad is the best option for you, namely in terms of your skills and priorities.

If your professional talents lie in something that is location-dependent, but you want the time and money to be able to travel wherever you want for as long as you want, don’t worry! Your time will come. Like my friend back home, you can build a business and eventually delegate everything (I know, I know, easier said than done).

Or, you can work a 9-5, stack cash and build an Internet business in your spare hours. Once you’ve replace your 9-5 income with clients/customers, congratulations, you’re free. On top of that, you’ll have a nice cushion due to what you’ve saved in your day job.

If you arrange it right, you can live in your home country and have 3 months or more out of the year to travel or live somewhere else. There is no sense in living permanently abroad if you have the money to enjoy the amenities and advantages of home, while taking numerous trips.

If you truly hate where you’re living, see if your skillset is in demand in a foreign country that you like. I believe that we are not all suited to the places we were born, thus I am a big advocate of expatriation (I will talk more about this shortly).


Still Want to be a Digital Nomad? Here are my Recommendations

I did everything wrong when I started out, and I’m still suffering consequences for that. If I would have stayed in Canada for just a year or two more, I’d be in a much better financial position now.

But I wasn’t willing to wait. If I didn’t go abroad when I did, I felt I never would have done it.

In other words, if you have similar feelings, I can empathize.

If you are truly unhappy with where you are living, don’t have many marketable skills, have little savings and want to get out there and see the world, here’s what you should do.


Have questions?  Skip the guesswork…

Schedule Your Personal Consultation With My Latin Life


1. Have your work situation figured out before you go

The moment I made $500 a month online I decided I’d go abroad and work from my computer.

If I can make $500, I’m sure I can make $5000, I told myself. I’ll just work harder.

This kind of thinking resulted in me living off bread and boiled water my first two months in Mexico City. My copywriting, content writing and proofreading clients unexpectedly dropped off the map and I was left without a way to make money. The proofreading client eventually re-appeared, but I was forced to compete with other contractors for projects on a first come, first serve basis (i.e. first freelancer to click ‘accept’ for a project would get that project).

This resulted in me sitting in front of my computer all day in an attempt to be the first to accept an assignment, all in order to earn less than $100 a day.

Before you even think of moving abroad, make sure you have a steady and consistent stream of income that will cover your living expenses. Don’t try to figure things out as you go along.

…And never stop hustling for more work. Especially if you’re freelancing, you never know when it’s going to go south and regular clients are going to drop off.


2. Don’t start a blog for money

Luckily I didn’t start My Latin Life for money.

I simply had 2 notebooks full of travel information that I wanted to share with the world. I wanted to write stuff about Latin America because I couldn’t find many good websites about it on the Internet. I wanted to help people like myself. If money were my goal for this blog I would have given up long ago.

Fortunately, last year a fellow blogger gave me advice on how to monetize my site. It now earns close to $1000 each month.

But that’s nothing compared to the hours and time I’ve dumped into it. Don’t get me wrong, it’s nice to have a bit of extra spending money, but my blog has never been and never will be my main money making priority.

If you want to make money online, I highly recommend starting a service business instead of a blog.

Here are some examples of businesses anyone can start anywhere, through self-education and with minimal overhead:


Copywriting Service

Proofreading Service

Ghostwriting Service

SEO Service

Market Research Service

Graphic Design Service

Translation Service (delegate to native speakers on UpWork)


Learn some SEO, throw some Facebook ads at it and cold email potential clients. If you have a decent website, you should be able to get 1-3 clients per every 100 emails you send.

Another hack to this would be focusing on a local market. For instance, if you have a site that is SEO’d for “medical copywriting services in Charleston, South Carolina”, you have a much better chance of being seen than if you attempt to SEO a site for just “copywriting.”

One thing that might mess you up is that some clients will want to meet in person. Since you probably won’t be in the city you’re choosing to target, you’ll have to fudge it a little. If you run into this, make up an excuse and try to arrange communication through Skype and email.

I’ve personally experimented with both a copywriting and proofreading website. Unfortunately, I let them both get worse because I tried to delegate too quickly and messed up on too many deadlines and submitted low-quality work (I had such little faith that I’d be able to get clients that I didn’t even include a payment option on the sites!).

I was surprised to find out just how easy it was to attract paying customers with a decent-looking website and a thoughtful pitch. Even though I cocked it up, I immediately saw that the ROI on a service-based website was much better and faster than on a niche site or a blog.

If you can learn to manage clients and freelancers, a service business is a great way to procure a nice stream of semi-passive income.

P.S. If you’re looking for a model to follow for someone focusing on a service-based business, check out what Dylan Madden from Calm And Collected is doing. He’s got it right. In a few years time, I’m 100% sure he’ll have the money and freedom to travel whenever he pleases.


3. Consider expatriating instead

I now wholeheartedly believe that expatriation is a better longterm plan than digital nomadism. I’ve missed out on countless opportunities simply because I didn’t want to tie myself down to one place. Opportunities which, ironically, could have granted me more money and time to travel in the long run than anything I’m doing now.

The sense of having a permanent location puts you in a different mindset.


It allows you to explore more opportunities in terms of making money.

It allows you to be part of a community.

It allows you to have your favourite bars and restaurants on lock.

It allows more opportunities for social networking.


If you’re always moving around you will have to constantly rely on your own savvy to earn a living. That’s an excellent skill to hone, but you’ll be able to leverage yourself much better if you have some connections and if you have greater knowledge about how the place your living works.

This comes only with time.

You’ll also save money. You’ll find much better deals on apartments if you stay longterm in a place, and you’ll learn numerous other ways to cut costs. If you have it together, you’ll still be able to take a few trips a year, and perhaps even earn a bit of passive income by renting out your apartment on Airbnb while you’re gone.

Best of both worlds.

What is Next For Me?

So after spending the past hour or so speaking condescendingly about digital nomads, you’re likely wondering if I see the irony in the fact that I, by definition, am a digital nomad.

“Digital nomads are people who are location independent and use technology to perform their job.”

— Investopedia

I get it, a bit hypocritical.

That’s why I’m changing my tune.

I’m making plans to relocate. In 2018, the place I will be is the place I intend to stay (with the exception of border hops *if necessary* and trips to Canada to see my family).

I’ll be shifting my focus to include offline ventures in addition to online. It was never my goal to work exclusively from my computer – the idea of making my entire living from running 20 niche sites or selling e-books does not appeal to me…at all.

But I get that there’s a lot of money to be had on the Internet, so it would be stupid not to try to catch some of it.

What city will I choose?

You’ll find out soon enough!


Thanks for listening.

Your friend,


Looking for that perfect Latin American city to set up shop? Check out My City Guides


Have questions?  Skip the guesswork…

Schedule Your Personal Consultation With My Latin Life