Digital Nomad Secrets

Kent Stuver
11 min readDec 9, 2021

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How to live and earn on the road, even if you have a family.

The Gen Z has latched onto the digital nomad lifestyle. But what if you have a family? Has the digital nomad dream passed you by? Are there any options for you to be able to live and earn your income wherever you want to?

One of the biggest challenges is just to identify what kind of digital nomad you want to be.

The term “digital nomad” has been used by so many people in so many ways to describe so many different types of lifestyles that it can get pretty confusing. And each digital nomad lifestyle-type has its own set of plusses, minuses, and pitfalls.

The reality is that, if you have the desire to travel and are willing to adapt how you earn your income, you can probably find a digital nomad style that works for you–AND your family.

See also:

Digital Nomad — A New Normal

You know, it’s become the ideal of the millennium….Sitting with your laptop on the beach while you work. And, being able to work any place and any time you want to — anywhere in the world.

At the pool, in the mountains, at the park, in the forest… as long as you have your laptop computer and a connection to the internet, you can work.

But what does it really mean to be a digital nomad? There are several distinct types of digital nomadism that may not seem to have a lot in common.

So, it’s important to have the complete understanding of what all the options are, otherwise you may pass up on an option that would be ideal for you, simply because you don’t know it exists. (Or, because some other “digital nomad guru” doesn’t think your thing is really digital nomadism.)

And, how can you get started in this lifestyle?

More importantly, how can you avoid the pitfalls…?

‘Cuz I gotta tell ya…. There are some doozies out there for people who try to jump into the laptop lifestyle without taking the right steps.

What Is This Digital Nomad Thing, Anyway?

In this post, I’ll describe several different styles or types of digital nomadism. They are actually very different, but all have been referred to by different people at different times as being “digital nomads”.

In fact, I’ve even heard digital nomad gurus say that their own style of digital nomadism is the only true and legitimate form of digital nomadism…And nothing else qualifies.

Kinda crazy, eh?

Each style has different plusses and minuses. And each style has different considerations based on your own personal circumstances.

So, let’s start by taking a sec to get on the same page.

Unbridled Jetsetting?

The idea of digital nomadism is over two decades old. In 1997, a Hitachi executive named Tsugio Makimoto wrote a book called (appropriately) Digital Nomad, with his co-author David Manners.

Makimoto predicted that high-speed wireless networks and low-cost mobile devices would break the link between occupation and location.

The public pretty much ignored his book.

Ten years later, Tim Ferriss wrote his epic bestseller, The 4-Hour Workweek: Escape 9–5, Live Anywhere, and Join the New Rich. Tim painted a seductive picture of unbridled jet setting that very few people were able to grasp at the time.

But the idea and ideal of being a digital nomad received tons of press time, even if only as a wish and a fantasy.

Today, the ability to actually be a digital nomad has gone mainstream. Nearly anyone can create a situation where you can live as a digital nomad of some kind.

Most importantly, the economy and the workplace has adopted the idea of remote work, which is making the reality of being a digital nomad more and more feasible.

There’s now an entire industry around co-working spaces, for example, which are essentially offices on the go.

Even trendsetters like Air BnB, Uber, and Lyft are playing a role in how easy it is for people to adopt certain styles of digital nomadism.

The Laptop Lifestyle

It’s basically this simple at the core: If you have a laptop computer and a good connection to the internet, then you can work anywhere in the world that you want to.

This is often called a location-independent income. And, it’s the key requirement to be a true digital nomad.

A secondary aspect of being a digital nomad is that your income is time-independent. This simply means that you can work when you want to.

Time-independent income is a little less critical to digital nomadism. But certain digital nomad styles benefit more from time-independent income than others do.

To a large extent, the type of location-independent income you can create will have a lot to do with what kind of digital nomad lifestyle will make the most sense for you. So, I’ll start by talking about the types of location-independent income that are possible.

Then, I’ll talk about the digital nomad styles.

Digital Nomad Money Matters

Three main types of income can support a digital nomad lifestyle. There’s also a fourth type, which isn’t strictly a location-independent or digital nomad income type. But, since it’s compatible with certain types of digital nomad lifestyles, I’ll mention it here.

Remote Employee

In many ways, being a remote employee can be one of the quickest paths to a location-independent income.

In some cases, it can be as easy as making an arrangement with your current employer. More and more mainstream companies are creating policies that are friendly to remote work.

But, if your current company won’t work with you, you may be able to find another employer who will, without too much difficulty.

Many new startups are being founded from the ground up with the expectation that ALL employees are remote employees. And, several new job sites have sprung up that are focused on job listings for remote work only.

Being a remote employee, though, can be one of the least time-independent income types. In fact, it might be very time-inflexible.

You’ll often need to work according to your employer’s office hours, no matter where in the world you are. And, some employers who offer remote work may require that you are physically in their office periodically.

See also: 4 Steps to Create a Digital Nomad Income as a Remote Employee

Freelancer

The freelancer income type is a nice blend of location-independence and time-flexibility. But, there’s often a learning curve in getting started, as well as some ramp-up time to create a big enough income to meet your needs.

As a freelancer, you have a skill that people want to pay for, but that they don’t necessarily want to hire someone full-time for. An example might be something like graphical design, programming, copywriting, or social media marketing.

Many freelancers list their skills availability on freelancer marketplace sites. And, as potential clients need skills such as yours, they go to these websites and search to see which freelancers are available and what their specific service offerings are.

Freelancing is typically location-independent because you usually do the work from wherever you are.

It is somewhat time-flexible in that you only accept those clients that you choose to, and that you generally perform the work according to your own schedule.

But there’s also an element of time-inflexibility: once you accept a client assignment, the client will generally have a deadline that you need to work quickly to meet, even if it’s inconvenient.

See also:

  1. 5 Compelling Reasons To Start Freelancing
  2. Freelance Work: 5 Easy Steps to Start
  3. 4 Steps to Create a Digital Nomad Income as a Freelancer

Online Entrepreneur

Being an online entrepreneur is one of the most location-independent and time-independent income types out there.

In fact, more than any other, the online entrepreneur income type most resembles the dream of making money while you sleep or while you relax on the beach.

It also has a pretty significant learning curve and ramp-up time. So, this is often an option to pursue as a long game, while working as either a remote employee or as a freelancer.

It also has several sub-categories. An online entrepreneur can use one or more of these strategies.

  1. Affiliate Marketer
  2. Content Creator
  3. Course Creator
  4. Ecommerce Marketer
  5. Online Networker

See also: 5 Online Entrepreneur Types (Which Are You?)

Seasonal Employee

Being a seasonal employee doesn’t truly fit the digital nomad characteristics. But it can work with certain digital nomad lifestyles, so I’ll mention it here.

As a seasonal employee, you may work at a particular location for 3 to 18 months, then move on to a new work location in an entirely different part of the country.

Because of the short time in each location, traditional housing arrangements, like buying a house or renting an apartment, may not work out well. And, a couple of the digital nomad lifestyle types are ideal for seasonal employees.

Digital Nomad Lifestyle: It’s A Matter Of Preference

Remember, the digital nomad lifestyle is all about the flexibility to live how and where you want to. And, it’s very common to start out in one digital nomad lifestyle, and then to change over time to a different digital nomad lifestyle.

It’s also possible to live a hybrid lifestyle–one lifestyle type for part of the year and another lifestyle type for another part of the year.

So here are the basic digital nomad lifestyle types.

The Jet Setter Digital Nomad

Living the Jet Setter digital nomad lifestyle is all about seeing the world — and as much of it as possible.

If you’re a Jet Setter, you carry all your active belongings in a couple of suitcases and travel full-time.

You stay a week to a couple of months in a given location, then move to your next destination.

A Jet Setter will typically not own a house or rent an apartment. Instead, you’ll live in a hostel, a co-living accommodation, or an Air BnB-type place.

You’ll often work remotely from a co-working facility, but frankly, anywhere you’ve got your laptop and your internet connection will do: by the pool, at the beach, at a park, or wherever.

Family Prospects

This is the digital nomad lifestyle that Tim Ferriss initially advocated in The 4-Hour Workweek, and even today some high-profile millionaires follow this lifestyle.

It is also the digital nomad style that you might be most familiar with. It’s the style that millennials have adopted like crazy. And it’s perfect for unattached singles or couples.

The Jet Setter style, however, isn’t well adapted to people who are more advanced in life, or who have families. Some GenX’ers have successfully lived the Jet Setter style with their families. However, it’s usually only been for a couple of years before they’ve found a place they like to settle down a little.

And, speaking of…

The Expat Digital Nomad

Following the Expat digital nomad lifestyle is about finding a place to settle down a little.

It’s about falling in love with an (often) exotic locale and staying a while to get to know it a little better. But it’s a place anywhere in the world, regardless of where your income may come from.

For example, you may work as a coder, or as a social media manager, or as a customer service rep for a large, well-known company… But, you live in Chiang-Mai, Thailand, or San Jose, Costa Rica, and do all your work remotely.

Since you’re there for 6 months — ?? years, you’ll usually find a local apartment to rent.

Family Prospects

With the Expat digital nomad style, prospects are pretty good for families. There’s one caveat, however. You need to know where you want to spend some time.

Most Expats start as Jetsetters, and through the course of their travels, find the place that they fall in love with. With a family, you may not have the luxury of that extended period of roaming to find your dream location. If you haven’t had other reasons to travel extensively, you likely haven’t found that place yet.

There’s another benefit of Jetsetting before switching to the Expat style. As a Jetsetter, you often get to know a location in ways that tourists seldom can.

If the Expat digital nomad style interests you, then here’s an option. Check out the cities that are recommended for digital nomads to live in. When you see one that interests you, schedule a vacation there with your family. See if you can get in touch with a digital nomad living there who’s willing to meet up with you and show you around.

You may want to do this several times, and talk to several different digital nomads in the area. Then, if it still feels right, you can move forward with your plans.

FullTime RV’er Digital Nomad

In many ways, the RV’er digital nomad lifestyle is a hybrid between the Jetsetter and the Expat lifestyle.

It’s all about taking your home with you, in the form of a motorhome or a travel trailer, and working remotely while you travel the highways and byways of a country or a continent.

In Europe, and other parts of the world, RV’ing is often referred to as caravanning, and a recreational vehicle is often called a caravan.

Within the RV community, you may refer to yourself as a full-time RV’er, or even just a fulltimer.

If you’re already familiar with RV’ing (especially if you already have a rig that works well for you), then it can be a straight-forward transition to the digital nomad life.

If not, then the ramp-up time can be a bit longer than for some of the other digital nomad lifestyles.

The RV’ing digital nomad lifestyle can be full-time or part-time.

When Darlene and I jumped into the RV’ing digital nomad lifestyle, we sold our 5,500 square-foot house, bought a 37-foot fifth-wheel trailer, and chose to live in the fifth-wheel full-time.

We know several friends who did something similar, and now live on the road with their families.

The RV’er digital nomad lifestyle actually has several sub-variations, which are important when deciding which type of recreational vehicle to get.

  1. Seasonal RV’er
  2. Touring RV’er
  3. Boondocker
  4. Van-Lifer

Family Prospects

In many ways, the Fulltime RV-er digital nomad style is one that is best suited for families. As long as you are clear on the RV-er sub-variation you want to pursue, and as long as you choose an RV that fits your family well and meets your desired level of mobility, you’re good to go.

Many families live the Fulltime RV-er lifestyle. The “Fulltime Families” organization provides support for RV-ing families with children, including events to connect with other families and roadschooling assistance. The “XScapers” organization focuses on GenX’ers or Millenials who are Fulltimers, many of whom have families.

You have lots of resources and lots of support, and you’re part of a large community. As long as you are happy with travelling around your continent, instead of travelling the world, it’s a great option.

More Specialized Digital Nomad Styles

There are a couple of specialized digital nomad lifestyle types.

Lots of people live these digital nomad lifestyles, but jumping into them without knowing what you’re doing can create life-and-death situations.

So, you really need to become familiar with them as hobbies first, before you try to adopt them as full-time digital nomad lifestyles.

These are: Sailing, bicycling, and backpacking.

In the end, it really doesn’t matter what life-stage you’re at. If you have the desire to travel and are willing to adapt how you earn your income, you can find a digital nomad style that will work for you.

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Kent Stuver

Author. Solopreneur. Gen-X Nomad. Copywriter. Online Marketer. Husband. Grandpa. Sax Player.