Why Thousands of Digital Nomads Failed to Sustain the Lifestyle

By Sean Ogle •  Updated: 07/16/19 •  8 min read

2007 might have been my most important year ever.

The stock market was at an all time high.

I was graduating college and entering the real world.

And the Four Hour Workweek was published by Tim Ferriss.

For myself (and many others), this was the beginning of a perfect storm of circumstances that would forever change the direction of our lives.

While I was in college the terms “lifestyle business,” “solopreneur,” and “digital nomad” didn’t exist – or at least not in the widely used ways they are today.

I studied finance and learned all sorts of things that would help my dreams of travel and entrepreneurship. Things such as the Black-Scholes options model, how to read balance sheets for major corporations, and advanced calculus that I still haven’t thought about since the minute I turned in my final.

Sense the sarcasm…

After graduation I entered the real world, and was stoked to don my suit and tie.

It only took a few months to realize how miserable it is to have to put on a suit every morning.

Within months of entering the real world, the stock market began to crash, banks began to fail, and I found myself yearning for the adventure I never got to have post college.

How the Recession Created the Digital Nomad

By 2009, the sky was falling.

Everyone was panicked.

From the baby boomers who were seeing their retirement complete disintegrate in front of their eyes, to the recent college grads that were now having to pay back their student loans, but couldn’t find jobs – everyone was beginning to feel the effect.

So when The Four Hour Workweek came out, many people treated it as an escape from the very bleak reality of their own lives.

For $19.95 it allowed them to dream of becoming a world class tango dancer, or to leave it all behind to move to Brazil and open up a small dive shop in paradise.

I took my own Brazilian adventure in February of 2009 - it was the beginning of the end for my day job. This is Igauzu Falls.

I took my own Brazilian adventure in February of 2009 – it was the beginning of the end for my day job. This is Igauzu Falls.

Just as millions of people bought their $2 powerball ticket this year to allow themselves to dream, the FHWW let them dream – but made the odds of success seem much more attainable.

Around this time, there were a handful of blogs popping up that specifically talked about travel and working online.

The three at the time that most readily come to mind are:

These were all people either living or traveling to exotic locations while building small businesses from their laptop.

These were the blogs that made the idea of the digital nomad become a truly obtainable thing.

Thus the perfect trifecta for the rise of the digital nomad fell into place:

I know this, because I was at the forefront of this revolution.

Digital Nomad Fail: The Rise of the Wantrepre-Nomad

By 2009, I’d completely bought in.

I read those blogs mentioned above religiously.

I used all of my vacation time for the year to take my dream trip down to Brazil for Carnival.

The day of my return I was given a 20% cut in my pay, which was never reinstated.

By the end of the year I left my job as a portfolio analyst with a dream to travel the world before ever going back to a real job.

And I picked the most stereotypical place to begin my journey (and the defacto hub of every new digital nomad) Thailand.

Note: A huge thank you to Dan Andrews for helping me make this happen.

While some of the particulars were unique to me, the general story was not.

Thousands of people over the next few years went through their own version of this.

Thousands of digital nomads were born as those who couldn’t find jobs hit the road, started their blog, and set out to become the next Tim Ferriss.

However, how many of these people became actual digital nomads, or built actual businesses?

Not many.

I met hundreds of people and saw hundreds of new travel blogs or blogs about remote working hit the interwebs from 2009-2012.

Do you know how many of them are still around today?

Not many.

Do you know how many of them are legitimate businesses?

Even fewer.

While the idea of a digital nomad got a lot of people to travel, most of those people fell into one of the following buckets:

At the time, I didn’t know what was happening, and I certainly I didn’t expect Location 180 to turn into a viable business that would help thousands of people over the years.

I didn’t expect to truly be able to stay away from a day job for many years to come.

I didn’t expect my life’s trajectory to be changed in such a profound way.

But I did, and it was.

The New “Nomad”

One of the primary reasons I think so many people packed it in and went home during this time was because honestly, they didn’t know any better.

There wasn’t a whole lot of information out there that actually provided a roadmap for how to sustain a business on the road.

A blog on it’s own isn’t a business model, and for many the idea of a niche site, info product, or e-commerce store was daunting without the marketing know-how to go about it.

Too many people tried to start at the end, rather than the beginning.

You wouldn’t graduate college and go out and buy a million dollar house in the hills after landing your first entry level job, would you?

You wouldn’t run a marathon without having trained for months beforehand?

Ok. Bad example.

The point is, too many people tried to go for the sexy businesses, rather than start from the ground up and build their knowledge and confidence.

And a lot of people, simply didn’t consider all of the downsides to becoming a digital nomad.

So how do you do it all, successfully?

You start with the boring stuff.

You learn the proper skills. Things like copywriting, SEO, social media for business, WordPress, basic design etc.

These are the skills that will come in handy no matter what you do online.


Rather than trying to generate passive income up front, you generate active income through freelancing.

Choose one of those skills that you really excel at and find clients on a freelance basis. That will build both your income and your confidence, and it will keep you from making the same mistake so many “digital nomads” have made over the last 7 years.

Then after you’ve built that foundation, that’s when you get into the fun passive income opportunities like affiliate marketing, info products, SaaS apps, e-commerce etc.

And the good news?

You don’t have to move some place exotic to run your business.

You can do it from your dining room table.

Or Starbucks.

Or Bali, if that’s really what you want.

The myth of the digital nomad, doesn’t have to actually be a myth anymore.

And that’s what I’ve set out to prove with Location Rebel Academy. We teach you how to do all of this, and while it may not be super sexy at first, if you follow the plan as it’s laid out, your life will be pretty amazing before too long.

Sure, there’s a lot of people that have packed it in, but there are a ton of people who have followed this model and achieved incredible success.

It takes a bit of patience and discipline to forgo the shiny object that is passive income, but I promise you, if you wait it out and invest in yourself and your business the right way – you will truly be able to have a life that most people would kill for.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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