Last updated: February 16, 2017

A Look Into the Dark Side of Being a Digital Nomad

Online Business


(Hey gents, Kyle here. This is a guest post.)

Vance here from My Latin Life.

I still remember the first dollar I made online.

What a feeling.

Sure, I was proofreading e-books written in India for less than a dollar a page, but the minute I saw that deposit in my PayPal account, I realized one very important thing.

It’s possible.

It started in Havana, Cuba: the first step on my journey to a location independent life. I had just quit my job as a content writer for a marketing firm in Canada, and decided to use some of the money I’d saved to take a trip and clear my head. I didn’t know what I was going to do, I just knew I wanted to travel and see the places I wanted as a child. Cuba was one of these places.

It was never my dream to work on the Internet. But it was always my dream to travel. As a kid, I remember looking at a world map on my wall. My eyes would drift to Central and South America and I’d wonder, what’s going on down there. I couldn’t wait any longer. I had to discover a way to find out. And since I’d just left my job and didn’t have a trust fund, online income was the only answer I could think of.

When I got back to Canada, I immediately started to get to work. I spent everyday applying for work-from-home jobs on Craigslist and any other Internet job sites I could find.

The first month I received nothing but rejections.

Fortunately, I had savings from my job and I was debt-free thanks to scholarships throughout university, so I had a bit of a cushion. But the money wasn’t going to last forever.

After failing for two months, I finally had some luck.

I landed two contract positions that I’d found on Internet job sites. The first was editing e-books, and the second was writing the blog for a corporate survey company.

Neither job paid much: $25-$50 to edit 50 page e-books, and $20 for each 1000-word blog article, but I was thrilled nonetheless.

Over the next couple months, I landed a few gigs writing essays for students. In 4 months, I had exceeded the modest goal I’d set for myself: $500 a month.

Then I did something rash.

I used the rest of my savings to take a backpacking trip through Latin America. Now that I knew it was possible to make money online, I didn’t want to leave myself another option. Buy burning all my money on something I’d always wanted, and getting the taste of a life I’d always wanted, I knew I wouldn’t be able to go back. Nor would I have a fallback plan to allow me to do so.

(In retrospect, this was a short-sighted and financially retarded move, but it was also the most fun I’ve had in my life).

When I returned home, I took a sales job to cover the bills and got back to work on the online stuff. Eventually I got hired by two online proofreading and editing firms that offered the ability to earn $1000-$3000 a month, depending on how much I wanted to work.

That, in addition to some sporadic content writing gigs, was enough for me to take the leap and live abroad as a so-called “digital nomad.”

I booked a one-way ticket to Mexico City.

At first, things were incredible. I thought my dream had come true. Sure, my work all but dried up shortly after I arrived, I was going out too much and barely making ends meet, but each day was a new adventure. The mundanity of my job editing university papers, applications and business reports didn’t occur to me because I had a fun and active social life outside of work.

I was so hung up on chasing Mexican girls, partying and hanging out with friends in Mexico, any job that could support that seemed worth it.

Hell, I would have probably been happy working the drive-thru at McDonald’s if it meant I could keep living the way I was.

But, like anything, the novelty wore off. Working from home became my new normal, and I was bothered by the fact I still had to rely on someone else for my paycheck. I quickly found that unless you absolutely love what you’re doing or building your own business, it will get stale. For me, it took about a year to discover I hated my new job.

I realized that I was no different than an office wage-slave saving up for a new television or iPhone. Only my vices were drinking and partying.

A tough pill to swallow.

Nevertheless, I chose to ignore this ugly realization for another 8 months, after which time I went back home to spend the holidays with my family.

Thanks to a friend, I had a chance to return to an office job during the 3 months I was back in Canada. It was in the firearms industry, and they offered me excellent pay to write content for 3 new products they were launching. It was a unique opportunity to directly compare working online with working in an office, since I’d be doing both jobs at the same time. This allowed me to see what kind of work I liked better or, more accurately, hated less.

I thought about it. I knew I could use the money, but 3 months in a cubicle sounded cripplingly depressing. After taking that trip to Havana, I vowed never to spend another minute working in an office.

I decided to take the job.

Here’s what I came away with:

1. I hate working in an office more than almost any other kind of job

It isn’t so much the nature of the work, but the environment. Bright lights, uncomfortable chairs, mindless gossip. It’s mentally draining. Over the years I’ve worked on farms, in kitchens and on sales floors. My most recent stint in an office confirmed to me that office work is my least favorite way of earning money.

2. Freedom and flexibility are extremely important to me

I underestimated how nice it was to be able to start and end my day whenever I wanted; to take a midday break to walk in the park or buy groceries; to meet with friends for a long lunch. I found that not being able to do that when I returned to an office was detrimental to my well-being.

3. Many office workers are dead inside.

Generally, my co-workers were cool, but at least half of them clearly didn’t want to be there. Most of their days consisted of doing shit they didn’t want to do, and it was written all over their faces. They would constantly talk about their weekend plans because they didn’t want to face their weekday realities.

After the experience, I realized that although I didn’t like what I was doing, I enjoyed the freedom it afforded me – something that no office job could. It would be up to me and nobody else if I wanted to improve my situation and craft the life that I desired.

People with blogs that are living the location independent lifestyle tend to downplay the challenges of what it took to make it happen, or the daily struggle. I’m guilty of this. If you read my website, it probably looks like my life consists of jet-setting around exotic lands and having endless sex with Latinas. What I don’t tell you is about the times after arriving in Mexico City that I boiled tap water to drink because I didn’t want to pay for bottled water. Or staying in my apartment for weeks on end, eating one meal a day to save money. Or the psychological turmoil that came with realizing that my economic value wasn’t high enough to do much more than break even in a third world country.

Looking back, I made many stupid decisions when I was first starting out. I moved to another country before I had enough money or stable work to get by. I neglected work for women and booze. I failed to develop self-discipline or take my job seriously.

I’m doing much better now than when I started, but it certainly didn’t happen overnight. It took years before my blog made any money. I had 2 online businesses fail in the same week because I tried to outsource work too early. I finished copywriting jobs that I was never paid for.

I still make countless mistakes every day, but I’m learning. I’m taking action and trying new business ventures. Things look promising so far. I should be able to quit my proofreading job by the end of this year to focus on these new pursuits and never edit another essay again.

But even after a few years working online, I’m still very much an amateur at this.

Point is, if you decide to go this route you’ll be in the trenches, and you’ll be there for a long time. I know. I’m still there. But while you’re down here you’ll be able to live a life that many people dream of. While they’re drinking craft beers and watching their wives and girlfriends get fat, you’ll have the opportunity to learn languages and experience sights, sounds and women you never knew existed.

Just don’t get complacent. You’ll hit some roadblocks along the way, but always be striving for more. You don’t want to be the 40-year-old guy living off $2000 a month on a beach in Thailand. Personally, that possibility alone is enough to keep the fire burning.

Is location-independent life for everyone? No, it certainly is not. But if you feel a fervent desire to escape the corporate world – a desire that can’t be suppressed – you must pursue it. There is no other option. And if this describes you, you’ll know it. Whether that means sacrificing a few years of your life to start a successful business at home, scaling it and using your free time to travel, or if it means freelancing, selling e-books, drop-shipping or affiliate marketing. There is no right or wrong way to do it. Whatever works best for you. If you want it enough, you’ll find a way to make it work.

Despite many setbacks, uncertainties and personal errors – only a few of which I’ve outlined above – I no longer doubt that I’ve made the right decision. My most recent return to an office job confirmed this.

I’m never going back.

It’s been a rocky road, but blogs like This Is Trouble inspire me to make more money, build something I’m proud of and become a better man.

Who’s to say where I’ll be in a couple years. I have a plan but life doesn’t give a fuck about plans. It’ll hit you however it wants. But that’s part of the fun. If you develop skills and flexibility, two things that will come naturally as you try to make money online, you can adapt; you will be able to hit back and come out stronger.

That is important to remember.

See you on the other side,


You can check out Vance’s site at My Latin Life.

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Leave a Reply

  1. I guess that some people are fortunate to make so much money and do or go wherever they want without getting broke. I wish that I am one of them. I want to escape my BS job, make my blog and online business grow, and travel around the world with my future wife from Ukraine. I would do whatever it takes to make those things happen.

    Thanks to Vance for writing this helpful blog post for me and other men who want to escape our mediocre lives.

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