Last updated: July 18, 2017

4 Thoughts About the Digital Nomad Lifestyle After 1+ Year



It seems like it was just a month ago that I penned 25 Thoughts on Life on My 25th Birthday (I just turned 26 recently). I thought that life moved quickly in the first half of last year, but it’s not nothing compared to what happened in the year since. That’s what happens when you life the digital nomad lifestyle—life comes at you. Fast.

First off, let’s discuss what exactly the digital nomad lifestyle is. And, to make it easier, let’s not put a real definition on it.

Keep it broad—the digital nomad lifestyle comes down to getting out of a corporate job, dating abroad, traveling often, and just generally being free.

Even though I currently have a permanent place, I still consider myself to be living the digital nomad lifestyle. I’m still jetting (or training) places every month or so. I live abroad. And I work from my laptop.

So, no nit-picking me 🙂


Here’s 4 things I’ve learned and observed from my 1+ year of living the digital nomad lifestyle.

#1: There HAS To Be An End Game to the Digital Nomad Lifestyle

You know that feeling when you hate your corporate job? The feeling that you’re just…well, going nowhere.

The feeling that makes you feel trapped, stuck, and like there is simply no end in sight. Every day is the same. Hell, sometimes every hour is the same throughout the course of the week. The point is, there is no endgame. All you do is hope—hope that you save enough to retire one day and be rid of those florescent lights once and for all.

But, there’s something eerily similar when you start doing the digital nomad lifestyle.

What’s your end game going to be—because you need to have one.

“I’m going to travel and date hot foreign girls and work on the internet.” Yes, that’s a brilliant lifestyle. And a lot of fun. You simply need to define what comes next.

Be working towards something better. Speaking of which, let’s call out the elephant in the room.

digital nomad lifestyle

#2: Freelancing—The Evil Reality of Digital Nomads

Many, many of us who live this lifestyle start off with freelancing. And it doesn’t seem so bad on paper:

  1. Set your own hours. If you’re a night owl, early bird, or simply hate the actual 9-5 constraints—guess what, you get to work when you want.
  2. Location freedom. Self explanatory. Cheaper cost of living, better-looking and more feminine girls (let’s face it, most of us digital nomads are men), and simply a better overall life.
  3. “No boss”. Of course, this is wrong, because you’re still directly depending on someone to write you a check (or send you a PayPal payment).

But, there are problems with all 3 of these. And that’s why it’s so important to have an endgame.

  1. Do you have the discipline to set actual working hours? Or is the partying until 5am going to then force you to work 1pm-9pm, every day?
  2. Do you want to have to do all of your work on a 5-year-old-and-falling-apart 13″ MacBook Pro?
  3. Do you want to have to work 80 hours a week to finish an impossible deadline your best freelance client gave you?

Look, freelancing is a great way to get started—you have to hustle, and if you don’t—learn or die.

I was fortunate I didn’t do much of it at all—within a couple months I was only taking on the occasional web design job for the person who seemed fun to work with and paid the right salary. Don’t even ask how many freelance jobs I’ve politely passed on this year (or just never heard back from after giving a quote).

#3: The Hardest Part is Saying Goodbye

Have you ever heard the childhood stories of a military kid? How he or she had to constantly move around…always having to start a new school, with a new home, and worst of all—having to make a new set of friends.

Well, the digital nomad lifestyle includes a lot of these, too.

And while some of you may rightfully be assuming that I’m talking about girls, I’m actually talking about male friends. Good male friends are hard to come by, and the nomadic life has a way of making you fast friends. But that’s all they are—fast.

3 weeks later, they’re gone and you have no idea the next time you will see them (if ever).

I imagine it’s very similar to how military brats felt growing up. Never feeling like they had roots anywhere. The expectation that you’d be going and saying goodbye, and starting from scratch again.

This is the part of the life that nobody tells you about.

Speaking of…

digital nomad lifestyle

#4: No One Talks Reality

Here’s the thing—most who live the digital nomad lifestyle have similar thoughts to what I’m expressing here. However, it’s natural to talk only in a positive light, especially to those people who are unhappy in their 9-5.

The reality of the situation is that anything is better than that. Don’t think for one second that most people wouldn’t be happier freelancing and being relatively free as opposed to working a crappy cubicle job.

But…it’s just one step above, and has it’s own downfalls.

This just isn’t a conversation you have with people who are not digital nomads. To them, your life is shiny and full of adventure. They are so naturally gung-ho about it that you can’t help but be extremely positive when you talk to them.

It’s only among fellow nomad that these talks happen.

And that needs to change.

PS: If you want to avoid the freelance trap, make sure you start working on your own passive income projects. To learn how to make your first $100 easily, click here.

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