What Are the Stages of a Digital Nomad?

Gina Edwards Updated on March 29, 2020

digital nomad

Your journey is about to begin.

You’ve read The 4-Hour Workweek (well, the important parts anyway), your bags are packed, your ticket to Medellin is purchased, your online business is running – and now you’re poised to head off into the new, unchained adventure of work without walls.

You are ready to be… a digital nomad.

Except, you kinda have no idea what you’re getting into.

Sure, you’ve seen the online forums full of beachside laptop pics and followed all the #digitalnomad posts on Twitter and Instagram. What more is there to know? Right, guys? RIGHT!

Hmm…. hate to break it to you, but there is a lot of adventure to get yourself prepared for – and I’m not just talking about your trip to Machu Picchu down the line.

The lifestyle of a digital nomad (DN) is just that — a new kind of life. Not a vacation. Not even an RTW trip, per se.

It is a complete upheaval of the typical way of life and work — and here’s the key — replaced by a new way of life and work.

That’s right; unless you wind up stranded on a desert island (let’s hope not) or you have enough money to retire early (lookitchu), life and work go on – even as a DN. As with any big life alteration, the move to digital nomadism sparks a lot of changes, both internal and external.

It is not a singular, homogenous experience for all people, or even for one person.

No matter what you have heard, digital nomadism has its ups, downs, and challenges all around. Its unique nature warrants serious consideration before diving in.

Whether you’re considering the digital nomad life, getting ready to embark, starting out, or already on the journey, it is key to know the different stages of a digital nomad experience; this knowledge allows you to prepare yourself ahead of time (and/or adjust course as you go) to ensurethe best experience possible.

If you’d like to check out our video we did on how to become a digital nomad fast, check out our video below.

In this article we will walk through a few of what are considered the “typical” stages of the digital nomad life, as well as discuss some general advice for aspiring and current DNs.

Ready to go?

Stage 1: Honeymoon

Whether you’re already established or you’ve just booked your tickets out of town, let’s channel the moment you get on the plane to head to your first destination. Although there was likely months (or years) of previous saving, planning, packing, and goodbyes, for some DNs, the moment of boarding transportation is when the journey really begins.

You’re buckling your seatbelt in preparation to fly off to a new life. It’s exciting as shit, and rightly so!

Everything Is New and Wonderful

As you travel to your shiny new life, all the thoughts of possible new adventures scramble through your head.

What will the people be like? And the food? I wonder what the weather is there… Will I like it?

All of the freshness sparks promise and possibility, and as you prepare to enter this new place, you await all of the answers to these questions with excited anticipation.

Arriving at your new location means getting used to a new culture, language, currency and many other foreign (literally and figuratively) aspects of this lifestyle. At first, all of this stuff is particularly exhilarating, as it feels similar to other experiences you’ve had on vacation.

At the beginning, this novelty of experience confirms what you had imagined: that DN life is incredible. Like a new relationship, the first stage of digital nomad life is perhaps the most delicious and delirious.

Work Never Felt So Good

Despite the seeming familiarity of feeling like you’re on vacation, sooner or later you will have to do some work.

Depending on your situation, you may be a full-time freelancer, entrepreneur, remote employee, or other location independent worker. Regardless, you will set up your workspace and schedule, which at first, will likely be “anywhere with wifi” and “when I want to.”

For those who have never worked outside the traditional corporate structure, leaning into the notoriously loose structure of DN work style will likely provoke a series of incredulous questions.

No boss? No suit and tie? No commute?

Why would anyone choose to work any other way?

Indeed, the first several months of working as a digital nomad almost feel dreamlike, as you settle into the new normal of minimal structure and maximum freedom. Without the familiar-yet-stressful environment of a mundane office or neck-breathing boss, you seem to find inspiration at every turn.

Friends, Friends Everywhere

The first few months of the DN experience often tend to be the best for making friends. After all, experiencing a new place can be a lot more enjoyable with others who are doing the same.

Each new place relocated to, coworking space joined, and housing setup can be an opportunity for meeting, interacting, and collaborating with new people. The conversations naturally flow as you eagerly connect with other DNs.

Where are you from? Oh, I have an aunt from there!

How long have you been living the DN life? 2 years, wow!

What’s your favorite thing about [the place you’re in]? Cool, I’ll have to check that out!

Before you know it, you have new lunch companions, travel buddies, and coworking pals – and you’re living the dream.

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Stage 2: Grind

Nothing gold can stay – and the saying goes for digital nomads, too.

While the first several months of digital nomad existence might feel like floating on a cloud in comparison to your lifestyle before hitting the road, you’ll soon realize that it’s not all rainbows and that the DN life has unique challenges all its own.

For many, the second leg of the DN journey (be it several months or years into the experience) starts to shift from starry-eyed wonder to something a bit more familiar: the grind.

Novelties Become Frustrations

While the beginning phase of DN life might feel a lot like vacation, the longer you lean into the experience, the more it will start to feel like everyday life – except with problems that you never had before thrown into the mix.

The things that used to be novel and interesting become mundane, or even frustrating.

The language barrier might become a chore rather than a fun challenge, and the local food might go from being a tasty change to a disappointing necessity. You start to question if the “no shoes, no shirt, no problem” dress code was such a good idea after all, as you haven’t worn real clothes in weeks. Those cool new friends you met way back when either hit the road, or you start to realize they weren’t that cool after all.

In other words, the novelty starts to wear off.

Note that this can happen even if you move fairly frequently. Even the simple act of unpacking and repacking or catching transportation from here to there can start to feel like an unpleasant routine.

Sometimes the constancy of change starts to make you feel like you’re in a rut. Probably didn’t consider that paradox, huh?

Loneliness Sets In

On top of those newfound frustrations, depending on your situation, you may find that your digital nomad life starts feeling pretty lonely.

Sure, you could get together with the community of expats nearby or even try to get in with some locals, but if you’re the kind of person who appreciates a few deep friendships over a myriad of acquaintances, you’ll likely find yourself yearning for your squad back home.

Even if you are traveling with a significant other or friend, loneliness and isolation can still hit.

Even the most introverted among us often need regular and meaningful human interaction with others in order to stay happy and sane.

DNs eventually learn how to either comfortably create new networks of transient acquaintances, skillfully meet up with people along the way, or simply resign themselves to just having a smaller circle (perhaps even square or triangle) of individuals around.

Couple that with homesickness, and suddenly things aren’t as amazing as they once seemed.

While missing home may not be the sexiest topic in DN circles, it certainly warrants consideration. Even if you can go long stretches comfortably without seeing your family or friends, there’s a good chance that the DN life challenges will make you miss them more than you thought at the outset.

Work – Work – Work – Work – Work

Whenever this stage hits, not everyone responds in the healthiest way. In fact, many people end up doing the opposite of what the DN lifestyle was supposed to be: they work themselves to the bone.

The conversations that once happened with other similar people start to become internal dialogues that all seem to end in just doing more work.

Nothing to do tonight? Might as well get some work done.

No plans for the weekend? Guess I can check off those lingering to-do list items.

Don’t feel like meeting new people? Staying at home with the laptop is always an option.

You can see how easily people can get sucked into the “work over socializing” decision.

Especially, if, say, you are a freelancer who relies on the constant flow of new work to stay afloat, or an entrepreneur who is trying to get a business model rolling. Work can become the catch-all replacement for the elements of your former life that you once enjoyed.

The second stage of DN life may indeed be the most challenging and can be the sink or swim moment for many new digital nomads. Because it tests so many aspects of a person at once — emotionally, physically, geographically, and more — some people literally decide to pack up and call it quits at this point.

However, although precarious amounts of work might not be the best for one’s health, the result of that work can lead to the next (and more enjoyable) stage of the DN journey.

Stage 3: Abundance

As mentioned above, some aspects of the DN experience can make or break people in this lifestyle. Depending on the personality, type of work, location, and other factors, a DN may find that this way of living wasn’t all it was cracked up to be.

While the DN newbs and grinders certainly get to enjoy some of the benefits of the lifestyle, many of the richest aspects of the DN life come from the outcomes of purposefully planning  how to best enjoy those benefits; in other words, creating income streams that don’t require close involvement so that you can eventually free more time for yourself.

For those who stick it out, the final (and perhaps most rewarding) stage may be worth the wait and hard work: abundance.

Feeling Rich

This freedom to move about the world and take advantage of differences in currency exchange rates, cost of living, and the like can help long-term DNs live a “wealthy” lifestyle in other parts of the world.

Turns out, an apartment in Colombia or Thailand is a lot cheaper than one in San Francisco or London… who knew!

DNs can plan their place of residence according to what suits them, rather than opting to pay higher prices just to be in a specific place. While DNs may sacrifice living in the most cosmopolitan or sought after location, they can enjoy a high standard of living by opting to live elsewhere.

This can go for many different aspects of life depending on your location and priorities. Maybe you want a house by the beach and can’t afford it on the Italian Riviera, but it’s possible in Mexico. Or you want to eat like a king, but the price point of French gourmet just isn’t working out? Again, go to Mexico. (Personal bias – I love Mexican food.)

Ultimately, the DN lifestyle is one of choice — malleable and adaptable by those living it. Those who have given particular thought to using the freedom of DN life to create an experience according to their desires and values will find that this lifestyle offers the ability to truly create their life as they wish.

Work As Much As You Want

Largely speaking, the abundance stage finds those who have leveraged the DN lifestyle into their own location independent businesses with low levels of involvement.

While, of course, those starting out as freelancers and fledgling entrepreneurs enjoy location freedoms, those who have reached abundance stage feel a different kind of freedom, as they have moved from working in their business (weekly meetings, managing staff, minutiae) to on their business (bigger picture activities).

For many entrepreneurs and freelancers alike, this means working on the parts of their business they enjoy most, adding a great deal of personal and professional satisfaction.

This fact doesn’t mean that the business owner has abandoned their business, but that they have automated, outsourced, or otherwise removed themselves from it so that it can function without their input that often. (Note: this is actually a great business practice whether you are a DN or not!)

At this level, the business is also earning enough money to cover the DN’s expenses (and probably then some), so working on it all the time stops being a necessity.

When this financial sustainability is achieved, a DN becomes truly free to work (or not work) wherever and whenever they choose.

So, What Stage of DN Life Are You In?

As the internet allows for more individuals to shirk the confines of traditional life and work and opt for moving around the world with a laptop in hand, this way of life may start to become all the more commonplace. Office dwellers with 9 to 5 schedules may begin to ask themselves one of the simplest and most dangerous/exciting questions that lead them to a big life change: “Why not?”

For all those who have hopped on the train of this new wave of Digital Nomadism, the possibilities can seem endless — an open road.

However, just because the road is open, doesn’t mean it is without bumps, twists, and dips.

In the first stage of DN life, everything is great. The new places, the new people, the new experiences, the new way of working. It’s as though life as you know it has been reborn into a dreamy fantasyland! (Might be exaggerating a bit here, but it really does feel like a dream for many people.)

The second stage is where the fun (by which I mean hard) stuff hits. Think loneliness, homesickness, and out-of-country frustrations. It’s when the things that used to be fun turn into inconveniences, and when you may start questioning what you’re even doing in the first place. This stage can be the moment where DNs lean into their work as a way of coping – or take the completely opposite path and tap out.

For those who make it to the last phase, things start to look pretty good. By committing to true location independence and building a company that can largely run on its own, DNs can create true abundance through their lifestyle creation. Moving to remote places where their currency goes farther allows DNs to feel wealthy and attain a very high standard of living – even if their salaries relative to those back home aren’t as high. Combining these elements, DNs can reach the abundance phase of not only money but time, as their businesses can cover all of their basic expenses without taking up very much of their time.

Like any other big life transition, moving to the DN life carries its own set of unique characteristics, or stages, that those who espouse it go through. Regardless of what stage you’re in, it’s important to know what’s awaiting you on the other side of the plane ride. Maybe I’m biased, but I think you should take the leap.

Photo credit: ViewApart

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