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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21 comments on "Why Thousands of Digital Nomads Failed to Sustain the Lifestyle"

  1. Yes! Totally agree with this. I’ve done things the slow way, but I’m still here. I started freelancing, then created my first guided course, then grew my blog, then launched a self-study version of my course (my first bit of passive income!), grew the blog some more, then created another, better, more expensive course, which I am now adapting into a self-study course. Toss some affiliate links into the mix, and I’ve got a nice mix of active and passive income.

    I’ve been doing this for over three years now, and so far the only travel I’ve done since beginning is short trips – max 3 weeks (though I’ve been on a fair few of them!) – but I have laid the groundwork for a business that will actually be able to sustain me financially should I decide I want to travel long-term in the future. Hopefully for the rest of my life.

    And thanks to you Sean, for showing me how to get started all those years ago! 🙂

    1. Sean says:

      Just glad I could be a small part of the journey! But I’m the same way, yeah I took a few extended trips a few years ago, but now I feel pretty much the same way as you. I like taking shorter, more frequent trips. I still travel 3-4 months out of the year, I just take a different approach to it these days 🙂

  2. I think Google really did a number on a lot of passive income goals and online revenue goals. Know that the economy is getting worse again, maybe there will be a new revival of nomadic lifestyle design bloggers.

    Perseverance is key right? I agree with you that if anybody can stick it out for at least three years consistently they will make a survivable income stream online.


    1. Sean says:

      Definitely. It’ll certainly be interesting to see what happens in the next 5 years.

      And things were pretty easy when I was getting going. Google has gotten smarter, as have marketers and other business owners. But I still think consistency and discipline win out – if you put in the effort and time, you’ll have success.

    2. Joel says:

      This is a bad attitude to take.

      All Google did was get rid of the people who wanted the easy way out.

      It’s still easier than ever if you want to build a real business, but complaining that tactics that worked 5 years ago don’t work anymore isn’t the attitude of a business owner.

  3. Jessica Dusak says:

    I have to laugh, because my “big dream” was to run my business from Starbucks. Or the Public Library. Not super glamorous to some- but to me; dream come true. You can def. be a “homebody” digital nomad.

    My favorite office so far? Sitting in the middle of Nordstroms. It’s not Bali, but for a shopaholic, it’s close.

    1. Sean says:

      Trust me, you’re not the only one! Obviously with my marketing and stuff like that I appeal to the travel the world people – but the majority of my readers and LR members? They have pretty much the same goal as you – ok maybe not Nordstrom, but you get the idea 🙂

  4. Enzo says:

    I think the main reason people failed isn’t because they didn’t start with the “boring” stuff you’re saying, but because they failed and didn’t have the motivation to learn from their mistakes and fix them.

    You have to fail before you can succeed right? Whether that is when you’re starting out with freelancing or with a niche-site. Learn as you go and you will succeed eventually.

    This is my opinion though 🙂

    1. Sean says:

      Totally get that. But you can also make the argument that had they started focusing on building the skills first, and going through that learning process, then later failures may not have been as severe, and they’d then have the tools and knowledge to be able to properly address the mistakes and fix them.

      Appreciate the thoughts!

  5. Nick says:

    Thanks for posting. It seems like there is not enough written about how hard it is to actually start a business (waking up early to work while maintaining a full time job, working part time jobs while freelancing skills get good enough, etc. all while questioning yourself if what you’re doing is the right move and if there isn’t really something else that you’re supposed to be doing and that’s why your business isn’t taking off like you want it to) and so this is refreshing.

    I have learned these lessons the hard way and found that there really isn’t a lack of information out there for what to do, it’s more that sitting down and doing the right things is really, really challenging in the face of all the doubts and other things one could be doing (teaching English in Asia for example is relatively easy to pull off, provides a great quality of life, and lots of vacation time, but if you want to do something other than teach English forever, it’s going to take some hard work). Just my experience/interpretation clearly.

    1. Nick says:

      I’ve also found that focusing on the really tough things that will take your business to the next level (usually the things you’ve never done before) and not putting to much weight on everything else that needs to be done is what pushes the business forward. This will save you tons of energy which can be used for focus on the important things. Working well beats working more.

  6. Mel Wicks says:

    Hi Sean, great post. I think it’s a really important message – that it’s not all about glamorous travel and passive income from day one. You have to put in the hard yards. You have to build the foundations of a realistic income through freelance work before you can start to become truly independent. Then you can start to unshackle yourself and work from wherever the hell you want. And I’m not surprised that most of your readers are not ‘travel the world’ people. For a lot of people, unshackling themselves simply means the luxury of working from their back bedroom (or their local Starbucks), instead of donning the suit, fighting the rush hour traffic and working in a grey lined office, day after day. God, I’m getting depressed just thinking about it!

  7. As a business owner of both a web dev firm (now mostly quiet) and a high end audio mfg company since 1998, I appreciate your history and analysis of what went wrong for many. I used to hire a lot of you nomads — my best web developer was an American who lived in Spain for example. I have another reason for following your blog and I’d love everyone’s thoughs and ideas around this. I have a great lifestyle business in that I work from the second floor of our house with a team of about 5 people with our mfg less than five miles away. I have an amazing view of the river, my Springers at my feet and I love this setup. As the CFO, I have my hands on all the paperwork and finances in this business. What I’d love to do is figure out how to create a paperless accounting system so that I can do my work from anywhere. Not sure how much detail to get into here but I’ve got a full business with employees, invoices, parts inventory, etc. so it’s no small thing to set this up. And I am not hiring anyone to do this for me because my last hire became my marketing coordinator instead because she can write better than me and my next hire is the mfg manager, the EE, the sales engineer, etc. Is your site a good fit for talking about this — because if I want to do this, I am probably not the only one 🙂

  8. Jeca says:

    This is so true. As a freelance animator and illustrator, it really is a struggle to establish yourself as a legitimate and sustainable business without sufficient knowledge on how to start. It’s sad to think that art schools only focus only on teaching students how to design and use software, and not enough on the business side of art. Thankfully there are a lot of resources online about marketing, pricing, etc. However I wish I could’ve had the chance apply some business practices with mock scenarios in school…it definitely would’ve saved myself from a lot of embarrassing mistakes -_-

  9. Elisa says:

    I think on this a fair bit, probably more than actually deserves my brain space.

    Do you think that these people all ran out of money and/or “found higher paying, more secure jobs as the economy got better – and went home” — or did their lives just change?

    Don’t get me wrong, I am snarky as hell about the coconut cowboys I meet out here, flitting from shallow money-making scheme to English teaching gig to freelancing forays, but I also recognize that a big part of the shifts in lifestyle and business have to do with the way lives change and we, for lack of a better term, “grow up.”

    Digital nomadding first appealed to a number of people in their 20’s, rocked by a recession they weren’t equipped to experience (or oftentimes understand), disenchanted with a crumbling system and seeing a potential way out with their technological know-how.

    I don’t know about you, but my priorities and goals as a person in my 30s are much different than my priorities and goals were when I was in my 20s. Well, I’m a bad example, since I had a decade long stable career in finance and management in my 20s before I packed a backpack to start working and traveling at the age of 31.


    I do find myself having this conversation more and more with people who choose to move back and settle into a more “stable” life – whether that is buying a house or starting a family or taking a job rather than dealing with the (sometimes) hell of owning a business – that it isn’t about not being able to hack it out here.

    Instead, it’s about what they started out wanting. To be able to have enough control over their incomes, careers, and lives to have the ability to CHOOSE what they wanted to do. They are just choosing to not live out of a backpack bumping around various countries fighting out terrible wifi and Skype speeds to do business.

    (Says the digital nomad working on her business from the upstairs bench seat at Starbucks….in Thailand. 😉 )

  10. Martin says:

    I think the main issue was that many of these bloggers were all competing against each other and writing the same articles. They ran out of things to talk about after telling people how cool their trips were.

    What’s your favorite blog that went away?

  11. Halona Black says:

    I started out as a freelance writer and learned all of those great skills that lend to my newer business in being a book coach. Freelancing has been great, but I don’t love it. However it has provided a base where I learned how to hustle up clients, online marketing skills, wordpress, writing ebooks and print books, etc. All of those skills are things my coaching clients want to learn as well. Now I need to learn how to organize my own events and I’ll really be in business.

  12. April says:

    I had already gotten world travel out of my system when Ferris came along. However, like many, I clung to every word in his book.

    I still haven’t figured out how to make a real living online. Unless you are building your empire based on something like “how to make money online” blogs don’t really pay.

    I would be happy finding a regular gig that would allow me to work remotely. It would come in handy when I move my family to Canada. I’m tired of the commute and senseless meetings. Why are employers so old school?

    1. Sean says:

      Thanks for the comments April!

      I actually disagree with your statement about blogs not paying. I can think of dozens of blogs outside of that niche that do extremely well for themselves.

      Steve Kamb’s site nerdfitness.com, Elsie’s site abeautifulmess.com, my site breakingeighty.com

      Each of those are in three very different niches and each does very well monetarily.

  13. Wendy says:

    To Lori Ann Clark: There is a growing virtual accounting world, so, you should be able to have much, really all, of your accounting, recording needs taken care of. Just work with someone who knows what they are doing, regardless of the accounting programs they are using.
    Ingeneral, I think a business is a business, and most or many people that strive for a particular kind of business may be good, or get good at, being the technician, but that does not mean they know how to operate a business. You still need to know what your expenses are or will be,, how much you need to cover expenses, including taxes, like , if any, or how to reduce,or pay estimates) what kind of a profit you want, how will you get there,i.e. how many articles do you need to write, what fees will you charge, what fees actually get paid and when, etc.etc. So, I think it is important for those without, to get a fundamental understanding of running the operations part of your freelance business, then decide what you can do on your own, or who you might hire to assist you. So, in my opinion, along with the fundamentals of particular writing skills,(of course, or whatever your field might be) comes the need to gain fundamental understanding of managing business operations, expenses..profits and tax bears, oh my!

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