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Digital Nomads Screw This Up Big Time
This can wreak havoc on your emotions...
991 Words | 4 Min 8 Sec Read

Today we’ll be discussing one the largest problems faced by digital nomads and WiFi money business owners worldwide.
In particular, one that can wreak havoc on your emotions if you don't know how to deal with it.
Let’s dive in.
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When I quit my job to travel the world in 2010, the concept of being a digital nomad was unheard of.
At the time, Tim Ferris’ The 4-Hour Workweek was just one year old.
And while it might be hard to believe, back then, high-speed Wi-Fi was not a given. In fact, when I first ventured out in 2011, I had to travel with ethernet cables and my own Wi-Fi router incase the local Internet Cafe wasn't open.
Fast forward to today and you can get high-speed Wi-Fi in all but the most far-flung corners of the globe.
The reason I bring this up is because, as someone who’s been in this world for almost 15 years, I’m noticing a new trend developing.
It started with the rise of backpacking, which gained steam in the late 1990s and early 2000s.
Back then, however, working online was virtually unheard of.
Mainly because in 99% of cases, "work" was something you did in-person (assuming you weren't a traveling salesman). Along the same lines, the internet was still new, with very few opportunities for people to earn a legitimate living online.
In the late 2000s and early 2010s, however, that all changed.
From information products to consulting and agency services, I watched firsthand as the "digital nomad" movement exploded.
And really, it made perfect sense. Why?
Because being able to earn a living online solved the #1 problem that prevented backpackers from wandering the globe year round:
The ability to earn a living without having to be physically present in an office.
And because of that, the digital nomad movement gained serious momentum in the mid-2010s.
It was COVID, however, that blew the doors off the hinges.
Today, a record-setting number of people earn a living online while working from a foreign country. But as someone who’s been doing this for over a decade, I’ve started to notice something:
Despite being able to work from quite literally anywhere, the overwhelming majority of people I speak to are unhappy with where they’re living.
The reason why boils down to the Paradox of Choice.
According to the theory, if you only have to choose between three items on a menu, you’re much more likely to be satisfied with your choice.
However, if you’re facing a Cheesecake Factory-style menu with over 100 options, it can be exponentially harder to choose. And once you’ve chosen, you’re dramatically more likely to be unsatisfied with your choice. Why?
Because in the back of your head, you’re constantly questioning whether you would’ve been happier choosing something else.
And whether we're talking about something as inconsequential as choosing a dinner plate, or something as serious as choosing a life partner, the Paradox of Choice is always at play.
Which explains the precise conundrum most digital nomads find themselves in:
With the ability to work from anywhere, the process of choosing just one place to live can cause massive anxiety.
It’s the paradox of choice to an exponential degree. With no geographical limits, you can plant your flag most anywhere on planet Earth.
The problem is, no one city, town or neighborhood will check every box on your list of desired criteria.
Which, in turn, can leave you constantly questioning whether you should live somewhere else that does check ABC box.
While this may sound like a first-world problem (and honestly, it kind of is), it’s a massive problem nonetheless.
The solution?
There are a few.
First, being made aware of this behavior is by itself a good step in the right direction. As they say in AA:
"The first step is admitting you have a problem."
Second, understand you will never find the "perfect" location that ticks every single one of your boxes.
So instead of spending years trying to find your Shangrila, you're better off defining which of your criteria are most important, and which locations (out of the ones you're considering) are most aligned with those criteria.
Third, and the one many people are choosing, is to split their time between two or three places throughout the year.
In doing so, you eliminate the need for one location to meet every single one of your criteria. Because instead of depending on one location to tick every box, you can now get your needs met by living in two or three places.
For example, if you’re someone who likes the hustle and bustle - but you despise when your city becomes infested with tourists during the summer -maybe you decide to spend those months elsewhere.
This could work especially well if you like big cities, but also like far flung beaches or snow capped ski resorts.
In conclusion, while the digital nomad life might look fun on people’s Instagram highlights, understand we’re all human beings dealing with our own set of problems.
More important, if you’re struggling with the conundrum mentioned above, hopefully being aware of the paradox of choice—and giving yourself permission to split your time between multiple locations—can help you reduce some of that anxiety.
💡 Takeaway: The process of choosing somewhere to live has massive implications for most every area of your life, from taxes to dating options. However, by being aware of our brain's tendency to think the grass is greener on the other side - and giving yourself the flexibility to split your time - it is possible to be satisfied with where you're living.
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