Why Most Digital Nomads Fail Within Their First Year.
Over the last 12 years we’ve seen almost every digital nomad we’ve met fail. Why? The general reasons start with impossible dreams, poor planning, insufficient resources and unmarketable skills. Even doing everything right, there are the mental aspects of being a digital nomad which leads to many quitting. The grass isn’t always greener on the other side, in fact, it usually isn’t.
In this post I’ve cover the reasons why most digital nomads fail within their first year, exemplified by real life examples. And I’ll tell you why some, like us, have survived.
The Selling of the “Digital Nomad Dream”
Around 2010, the world still reeling from the Great Depression, books and blogs started promoting the “Digital Nomad dream”. Tim Ferriss wrote a book called the 4 hour Workweek which pushed the concept of leaving corporate America to start your own online business. Travel bloggers such as Nomadic Matt pushed it further, selling a life of travel and adventure where you could essentially earn big bucks writing content on a blog while sipping Piña Coladas by the pool.
When we started travelling full-time in 2014, we met young people who chased the dream. One was an American couple we met in Prague. They had read Nomadic Matt’s book and thought they could achieve his success. They went to all his meetups (drinking parties in European cities) hoping that his magic would rub off on them. The truth was that they barely made enough money to survive, despite working 100-hour weeks on their blog. They told us that they had spent 6 months in Thailand living in a corrugated metal shack.
Less than a year later they had stopped posting on their blog.
95% of these young people ended up quitting their digital nomad dream within a year. The truth is that blogging success is very, very difficult and that you’ll make more money working equivalent hours at McDonalds than you ever will on a blog. Nomadic Matt was successful because he was among the first people to ever have a digital travel blog. It was a novelty…and he capitalized on that.
If you’re pinning all your hopes on nothing more than a dream, chances are that you’ll be giving up on your Digital Nomad aspirations within a year.
Burnout
People who do make it as digital nomads have busy schedules and often burnout, especially if they are freelance writers or bloggers. If you are either of these, you usually have to travel to have material to write about. A travel blogger, for example, won’t be able to generate content if he/she doesn’t travel. You’re constantly on the move – great at first but it can get old fast for many. Add to that the conferences and events* that nomads usually attend to network and learn new skills. That’s just part of being an independent worker but it can also be mentally and physically draining.
* Logistics are important and time schedules tight, which is why most events arrange transport by charter bus such as BCS Bus Spain. It’s the best and most cost-effective way of getting people places.
We know of several travel bloggers that, in the end, decided to go back home. Working 9-5 was for them easier and more conducive to a healthier lifestyle.
Poor Planning
Poor planning can come in many forms but the one that most comes to mind is the bureaucratic red tape that might pull you back home. Perfect example: A middle-aged American couple that we met in Croatia who had been travelling the world for a year. In their 2nd year, their bank caught wind that they were no longer residents of the US and told them that they could no longer keep them as clients. Their investments were cashed out. The couple had to go back to the US to take care of their banking and eventually decided to abandon their lives as digital nomads.
We’ve met other people who’ve had issues with Capital gains taxes, healthcare and home insurance. These days there are a lot of resources for digital nomads (you can buy a virtual address or get a telephone number from your home country for example). Travelling is easy, it’s the stuff back home that can get you in trouble.
More: 9 pieces of Advice for those thinking of living a Nomadic Lifestyle
Loneliness and family
It’s very easy to feel loneliness when away from family. The idea of being a digital nomad might sound great, but being alone in a hotel room in a strange city can get to you. You’ll end up thinking of your family and questioning the lifestyle you chose.
Family medical emergencies may also put an end to your digital nomad dreams. We’ve seen it happen a few times where travellers have had to go back home to take care of loved ones.
Making money overseas is hard…even harder than back home
Yes, there are jobs for digital nomads, the most typical being as English teachers, bloggers, and freelancers. But they won’t make you rich. A young person might consider themselves well off if their digital nomad jobs fund their lifestyles. But what about the future? You won’t get a pension from your digital nomad job. Will you make enough to buy a house (which you may want to do at some point) or to fund your retirement? Let’s be honest: digital nomads these days are competing from people from all over the world as well as AI. It’s competitive and if you don’t have specialized skills you won’t put much money aside for the future.
Many digital nomads at some point realize that and go back home to work 9 – 5.
That brings up the ideal scenario: having a good job back home and being able to do that same job remotely. When we started our full-time travels in 2014, Lissette continued working remotely for her Montreal employer. She did that for 5 years. Imagine, you’re making a North American salary and paying expenses in a country where the cost of living might be half of what it is back home. You could be saving a lot of money.
On top of that, professional digital nomads are eligible for digital nomad visas in many places. Countries like Thailand, Portugal, Spain, Croatia and Costa Rica. So you could spend 1 year (minimum, most allow you to renew quite easily) living in a beautiful country and doing your job remotely.
How we’ve survived being digital nomads
It’s been 12 years since we left Canada. Since then we travelled the world and have lived in two countries (Croatia and Spain).
How we’ve survived that long being digital nomads:
- We made our money before becoming digital nomads. We had to wait until our mid-40’s, but by then we had our nest egg (which we haven’t touched).
- I touched on it above: Lissette was able to continue her Canadian job for 5 years while we were overseas. That was huge.
- About 6 years into having this blog, it finally started making money. Not Nomadic Matt-type money, but enough to fund our lifestyle and not have to dip into our investments. I’ll repeat it because some people still think you can become rich having a blog: you most likely won’t. It was always hard and, with AI, blogging has become harder. Another piece of advice: we’ve met people who started a blog just to make money. Their heart wasn’t in it. If you get into blogging it should be a passion, something you enjoy. It’ll make up for all the hard work you put into it.
- Have a backup. Before we started off in 2014, I did an online TEFL Certificate (Teaching English as a Foreign Language). Just as a backup. I also reached out to a few newspapers and got some freelance writing work, using this blog as my calling card. One thing I’ve learned from successful digital nomads is that all are flexible and adaptable.
- Slow travel. We saved a ton of money, didn’t burn out from excessive travel, and really got to know the places we were visiting. All about Slow Travel here.
This post isn’t meant to discourage you from becoming a digital nomad. It can be done, it just has to be planned consciously and considering all the pitfalls mentioned above. Done right, it is one of the most rewarding ways to live your life.
Related: Regrets of living a Nomadic life



Really useful read. This is the 7th bbqboy.net tab I’ve got open – I keep clicking the related article link at the bottom and can’t seem to stop.
I’m 29, in the UK, and a few months from a decision that determines whether any of this is possible for me. On one side, a software engineering role at a large bank: solid salary, pension, structured progression, and a 9-5 with fixed office days. On the other, a smaller design-led studio with an equally solid salary, where the work is already remote-friendly and flexible enough to make slow travel viable.
Your “ideal scenario” paragraph about keeping the job you already have and doing it somewhere cheaper is essentially a description of that second option. Your point about slow travel is one I’ve arrived at independently. It makes far more financial sense to use the 28+ night Airbnb discount, or a discounted monthly hostel stay, as a base to work from during the week and explore in the evenings and at weekends. The idea of travelling slow, settling into new places, finding a local gym and café, people, going for a morning run and simply getting to experience living/travelling in all these cities and places sounds fantastic.
I’ve tried to do the boring part properly: monthly costs modelled city by city against what renting a flat would actually cost me at home, a fixed percentage of income reserved for tax and another straight into savings, a buffer month of cash that doesn’t get spent, and monthly bases rather than constant movement. What surprised me is that the slow travel version comes out either the same or cheaper than staying in the UK once rent and commuting are accounted for. I feel what I’m trading is security and structure on one side, against flexibility and actually being able to live somewhere else for part of the year on the other. I’m aware that makes me more or less the person your post is warning about, with the one difference that I wouldn’t be inventing an income from scratch, just relocating one that already exists.
The question I’d put to you: you waited until your mid-40s and had your nest egg in place before going. If you’d been in my position at my age, without much savings but with the option of doing a stable job remotely, would you have gone earlier?
Interesting position you’re in! For me I would not at your age (29) because at the time I had other scenarios/issues:
– I had a young son. So it was an impossibility.
– I had a great job…but it wasn’t possible to do it remotely
– I didn’t have savings at that point
– I hadn’t met Lissette.
At that point in my life it was only a dream that I could work towards.
If I was single, had no dependents and had stable money, I would 100% have gone for it. What is holding you back? The only thing I would consider: are you jeopardizing future career options by making such a move? That’s “opportunity cost” and it can be a big one. If you decided to come back home after 5 years, would you be able to pick up where you left off?
We’re in the UK right now (for 3 months) and it’s so expensive. Done smartly, you could save lots of money taking your job on the road. But that’s the financial side, you also have to consider the loneliness issues etc. In my case I always had a strong sense of wanderlust and that drove me.
You should read this post: https://bbqboy.net/regrets-of-living-a-nomadic-life/
Good luck!
Your reasons for not going at that age are completely valid and make me feel quite lucky to even be in the position I’m in.
So to answer your first question honestly: opportunity cost is exactly what’s holding me back, and I’m not sure whether it’s something I’d be able to pick back up. The risk for me isn’t really the travel or the loneliness; I’m single, no dependents, and the money would be stable either way, plus I’ve solo travelled before and never felt that lonely and can make friends easily enough. I can relate to your sense of wanderlust! This is the first opportunity I’ve had to actually be able to work remotely and travel.
What makes that bet tempting is that the upside isn’t the salary, the two are roughly matched there. There’s profit share/equity, on the table at the smaller studio. If (IF) the business grows, what I earn grows with it, and there’s no ceiling set in advance. That’s the appeal and the risk.
Now, to answer your second question, I don’t think I’d be completely jeopardising future career options, but the two aren’t the same kind of experience. I’d still get the experience in building digital products but I won’t be getting the corporate engineering/financial side: scale, process, working inside a regulated environment, more secure employment and a name on the CV that a recruiter recognises. If I ever had to come home after five years and find another job in tech, I might struggle, depending on the market at the time. The plan was always to find a remote job or contract later in my career (just as Lissette did) – but now I’m faced with the option of beginning that right now.
I read the regrets post too. The storage one made me laugh; I could fit my life in a backpack, and using my parents as a fixed address is thankfully a real possibility. To complement your Thoreau quote, I’ve always been a fan of “less is more”.
Thanks Frank. Hope you’re at least, enjoying the UK?, and sorry about the prices.
These are issues you have to weigh. Nothing sure in life. I was fired/quit because I got into a fight with the new boss and that actually made my decision easier and accelerated when we left. Sometimes circumstances give you signs. And sometimes we just need a little push 🙂
All the best to you. Message me if you ever have questions!
You make a great point when you mentioned that you and your wife were already well established before making the journey, which alleviated a lot of stress. I think if you are in your twenties and thirties, it can be extremely difficult to just make it work without a solid transition plan from your 9-5 income to something remote. I noticed people who seemed the most successful and satisfied were programmers who established themselves with a company that let them work anywhere as long as they finished their projects on time. Tons of other people seemed to be winging it and barely getting by or traveling on family money.
I’m 31 and have not “made it” yet as a remote worker. I end up spending most of the year in the US doing unpleasant grunt jobs like Uber until I have something saved for a couple months of travel in a lower cost of living area, mostly in South America. I started doing this at 24 and lately it has started becoming less exciting. I do know some Spanish, but last time I went to Brazil and the language barrier was extreme there, causing me to feel alienated and stupid. I hate long flights and bus rides now more than I used to. I don’t really enjoy trying to chum it up with other remote workers either as they often are just looking to replicate their home lifestyle on the cheap, and gentrify the environment.
I enjoy getting out into nature and there are certainly still positive aspects, but I’ve found lately I’m getting really tired of the cycle of saving up in a shitty job at home, to traveling somewhere where I face cultural barriers like language, difficulty digesting foreign foods, and other added stressors. I enjoy myself most when hiking and surfing and do not like trying to integrate myself into foreign environments as much as I used to. I would rather have a job that was at least tolerable, which occupied my time and provided more structure. I’m thankful to have been able to travel but lately I’ve been getting more fatigued and am looking for stability and increased financial security.
Hi Reed,
Thank you for your comment, it’s very insightful.
Travel is tough, especially if you have to work to make ends meet. It all sounds glamourous but as you know, certain aspects get old fast. Getting on planes, substandard accommodation, varying food quality, not having steady friends…it can get to you.
The problem though (we’ve found) is that you get hooked to the lifestyle. Having a base and a stable lifestyle sounds good…but every time we’ve done it we’ve gotten bored about 6 months in. So it’s a bit of a catch-22. At some point we know will have to settle down (we’re older than you) and welcome and dread it at the same time.
All the best to you, one way or another things will work themselves out.
The best travel blogs are written by people who are independently wealthy, as this means the writer doesn’t depend on earning an income and therefore can write honestly about their experiences without “selling out” (becoming a marketer, lying, posting generic stuff of little value, sucking up to certain people and places, avoiding controversies etc.). You are in a similar position and this is why I find your blog valuable unlike most other travel blogs.
Thank you very much for the kind words RJA 🙂 What I would tell any blogger is that they have to have a voice. Not a fake voice, but their own style that is honest to them. You won’t appeal to everyone but some people (like you) will appreciate it. Being generic doesn’t help anyone, much less the blogger.