3 Important Questions You Need To Answer If You Want To Be A Digital Nomad

Be A Digital Nomad

I am a digital nomad.

What that means is that I work via the internet and I don’t have a permanent place that I call my “home”.

Digital implies that my work is connected in cyberspace and nomad implies that I’m always on the move.

Basically, I am allowed the freedom to travel around the world as long as I can connect to the internet long enough to get my job done.

NOTE: Before we move ahead, I want to mention that some digital nomads focus more on having a fulfilling internet career while others focus more on the “nomad” part- they have a passion for travel and work merely as a means to sustain that passion. While this is totally acceptable, I’m all about finding a job that you both love and will allow you to travel.

Being a digital nomad is an amazing, fulfilling, and enriching experience… for me.

But it’s not for everyone.

Most digital nomads I know are wanderlusters (people who love to travel), but some just love the freedom of being able to go anywhere at any time and communicate with their clientele/employers via the internet.

Others love the unpredictable nature and spontaneity of the lifestyle.

I’ll give you an example of what I’ve been up to recently:

  • One day I wanted to go to Indonesia. So I went to Indonesia, stayed there for a few months, did my work, and traveled around Indonesia. Then I wanted to go to Malaysia. So I went to Malaysia, stayed there for a few months, did my work, and traveled around Malaysia. Then I wanted to go back to the US to see my friends and family over the winter holidays. So I went to the US, stayed there for a couple months, did my work, and traveled around the US. Then I decided that I wanted to learn to speak Chinese. And now here I am, in Beijing, writing this article and 正在说汉语.

Here’s what I did this morning:

Digital Nomad Great Wall

I call this one: “Trying to look like no one is taking a picture of me.”

But I’m not always drinking tea on the Great Wall of China…

Sometimes I’m lounging on a tropical beach drinking out of a coconut. And other times, I’m holed up in a cafe for hours on end struggling to meet a deadline while fighting some really bad internet.

This is the unpredictable nature of my life.

But it’s this level of unpredictability that allows me to stay contented with my work.

For me, having any kind of solid routine or plan is dreadful. I just can’t do that.

I get stir crazy if I stay in one spot for too long. I need to move around a lot; because if I don’t, I’ll spiral into a fierce mania.

Depending on who you are, you could call that “wanderlust” or you could call it “fear of commitment”.

Whichever one it is (probably the latter), I need to move around.

So I’ve chosen this kind of lifestyle to satisfy both my “wanderlust” and my desire to do the kind of work that I find fulfilling.

The Work

This is the part many people get hung up on.

I mentioned this moments ago, but it needs to be mentioned again.

While being a digital nomad is great, having a bad job will suck all the enjoyment out of the digital nomadic lifestyle.

When choosing a digital nomad job, you need to make sure that you can a) support your lifestyle and b) find a job that you find fulfilling. Now, these are two obvious things when picking any job, but it’s particularly of importance when you’re a digital nomad.


Because being a digital nomad comes with many challenges. Unlike living and working in a stable environment, a nomadic lifestyle means that everything is always changing.

It’s often more draining than you would think to keep up with all these changes.

Digital nomad lifestyle

The only permanent thing is change.

The work you do needs to be a bedrock of stability for the hectic lifestyle of digital nomadicism.

I’ll write an article later on how to pick a digital nomad job, but for now, let me just say that if you love what you do and you can work remotely (not connected to an office), you’re in a prime position to be a digital nomad.

If you can adequately answer these three questions…

Three Questions You Need To Ask Yourself To See If You’re Ready To Be A Digital Nomad

1. Do you like stability?

I personally hate stability.

There’s an odd sense of comfort in knowing that everything around me is going to change very, very quickly.

But a lot of people don’t like that.

A lot of people like routines.

Again, I personally hate routines.

I love doing something new every day. I’m the guy who takes the long way home just so I can see something I’ve never seen before. I’m the guy who schedules “aimless wandering” time into my daily schedule. I’m the guy who goes to a different restaurant every day even though I know I can get exactly what I want at a restaurant I’ve already been to.

Wandering Digital Nomad

I think my hostel is around here somewhere…

But if you’re not me, and I’m pretty sure you aren’t, these things may sound like massive wastes of time.

And that’s totally cool…

You can try to be a more “efficient” nomad, but when you’re constantly in flux, maximizing efficiency is a major challenge.

Here’s a typical experience:

  • I go to a place. I stay there for a few days. I leave. I go to a new place. I stay there for a few days. I leave. I go to a new place. I stay there for a few days. I leave…

Every few days, there’s a new neighborhood/city/province/country, there’s a new hostel/guesthouse/hotel/tent, and every few days there are new friends.

Continually meeting and saying goodbye to new friends is probably the hardest part. Even I’ll admit that I’ve had to take breaks from meeting new friends from time to time.

It’s very hard to meet great people, experience great things together, and then abruptly leave… and then regularly repeat this cycle.

It’s like a mini-breakup every three days.


“I’ll probably never see you again. Have a nice life!”

Unless you have a very strongly defined set of values, this constant maneuvering between relationships will definitely cause you a lot of tension.

I used to joke with my Malaysian girlfriend that I was a full-time boyfriend working under a short-term contract.

Simply put:

There’s virtually no stability in the digital nomadic lifestyle, unless we have a steady job, which, for many of us, is not particularly easy to come by.

But again, if you can find work that is a) fulfilling and b) steady, you’ll always be able to fall back on this bedrock.

But if you really, really like stability, then being a digital nomad is probably not right for you.

2. Do you have anything you can’t leave behind?

I have created a life for myself where I don’t have any entanglements.

I don’t have:

  • Kids
  • A girlfriend/wife
  • An apartment
  • A dog/cat/tarantula
  • A mortgage (though I do have a decent amount of student loan debt)
  • A car
  • A litany of friends
  • Pressing engagements
  • An office job
  • An unused Wendy’s gift card
  • yadda yadda…

But alas, some people do have these things. And having any of these things tying you to a certain place would make perpetual travel very difficult.

If you have a family, you’re probably not going to get up and leave.

If you have a house, you’re probably not going to get up and leave.

If you have a car, you’re probably not going to get up and leave (though I have met people who literally left their car on the side of the road and moved to another continent).

While these things are all hurdles, it’s important to recognize that if the digital nomadic lifestyle is right for you, you can work around these entanglements.

Anything you can’t leave behind

“Dude, we are so ready for your new lifestyle…”

I have met digital nomad families- families that travel while one or both of the parents work a remote job.

They sell their house, sell their belongings, and start traveling. The kids get an education through living in different places around the world and the parents are able to sustain that level of travel with their internet work.

I have met many others who have had well-paying office jobs and who were in relationships with partners who did not support such digitally nomadic lifestyles. They broke up with their partners, left their boring office jobs, and started traveling and working on the road.

It all depends on what you want. Obviously, in the first example, this kind of relationship is built on shared values, and in the second example, this kind of relationship didn’t have a strong basis of shared values. This is not an article about building relationships, but if you and your partner can’t agree on core values, the relationship is probably not that strong.

Here’s a key phrase to remember:

  • Where there’s a will, there’s a way.

If being a digital nomad is right for you, you’ll surely find a way to make that happen.

But if your family is vehemently opposed to you traveling, and if you value your family above all else, being a digital nomad is probably not going to work out.

3. Can you take a huge leap of faith?

I touched on this in the last point, but it’s really important to expand upon.

If you want to be a digital nomad, you need to take a leap of faith.

We often want great opportunities to be handed to us, but that’s just not how anything happens.

You need to know that if what you want to be doing is working remotely and traveling the world, then you need to be doing that. You need to know that it’s never going to happen unless you make it happen.

You need to get up and go.

Get up and do it.

Right now.

Digital Nomad No Fear

I’ve never tried flying before…

If you need to tie up some loose ends first, then fine, do that. But if you’re using your entanglements as an excuse and are not actively working to find a workaround, then you are either not serious enough or are afraid to try.

If you’re not serious enough about leaving everything behind and throwing caution to the wind, then that’s fine. This is not the right kind of lifestyle for you.

But if you really, really, really want it and are just too afraid to take that leap of faith, then you need to re-examine your life.

If you’re on the fence about whether or not to sell your car and buy a plane ticket to (wherever), let me tell you, if you don’t take the leap of faith now, you will keep wasting time as you spiral further and further into a deep pit of despair.

I know… I’ve been there.

It sounds bizarre for most people in our culture to accept that in order to do the things we really want to do, we need to leave behind the status quo and fiercely move toward our goals.

If our goal is to be a remote working traveler, then that’s what we need to be driving toward.

There is no other option.

Being a digital nomad

Life exists outside of the dream of life.

It’s unwise to keep asking ourselves: “What if?”

We can’t keep doing that.

We need to get up and go.

And if you’re struck with worry, it’s OK. Everyone feels this worry.

But if you have the means (even a modest amount of money is enough to get started) and the desire (and if you’ve read this article this far, I’m assuming you have the desire), there’s no other option:

You need to take a leap of faith.

Is The Digital Nomad Lifestyle Right For You?

Being a digital nomad is a truly wonderful experience, and I am thankful each day that I wake up and am allowed to pursue not only my fulfilling career, but also my passion of travel and exploration.

If these two things are also valuable to you (or at least the wanderlust part), you should see if you can answer these three questions in this order:

  1. NO
  2. NO
  3. YES!!!

Again, I am not here to say that this kind of lifestyle is for everyone.

In fact, I’ve met many people who burn themselves out very quickly and return their previous lives due to the challenges that they inevitably face walking along this path.

I need to stress this: It’s not easy to be a digital nomad.

But if you value the sense of freedom that such a lifestyle gives you, it can be one of the most rewarding life choices you’ll ever make.

Here’s another clichéd saying you need to remember:

  • You never know until you try.

All you need to do is get out there and try.

If at this point you’ve fully decided that you’re ready to be a digital nomad, I have one final question for you:

Where in the world do you want to go?

Give me your answer in the comments section below!

Are you thinking about being a digital nomad? What’s holding you back? Are you currently a digital nomad? What do you find rewarding/challenging about your experience? Share your thoughts in the comments!

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