The Digital Nomad Dilemma: When Do I Stop Traveling Full-Time?

Every digital nomad will, at one point or another, ask themselves one question: do I carry on as a nomad, or become a settler? This is the digital nomad dilemma.
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High school me would never have imagined it. Steady income and the freedom to live and work around the world? You mean, there’s a life path other than going to college, getting a job, finding a partner, buying a house, having a few kids and settling for a vacation or two every year?

To be fair, I don’t think my teachers in the little town of Mendon, Masssachusetts had any concept of “remote work”. There’s no one to blame for not bringing this option to my attention. In fact, I’d argue that digital nomadism is still very much in its early stages. I always understood that I could work in another country (which is exactly how my journey abroad began in Thailand), but working remotely and traveling while doing so didn’t hit my radar until 2015. It wasn’t until 2016 that I actually put it into practice, starting out as a copywriter for a Thai travel company. The pay was minimal, but I felt like I’d hit the jackpot. I stuck to cheap places and with a decent internet connection I was able to work from countries like Turkey, Spain, and the Czech Republic. Later on I landed a role with a tech startup, and to this day it has enabled me to work and live in some pretty incredible spots.

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If you follow me on Instagram you might be under the illusion that digital nomad life is all rainbows, butterflies, and far-flung destinations. But remember, it’s all carefully curated. That’s not to say that the last 4+ years of nomadism haven’t been magical- because I assure you they have- but the lifestyle, as with anything, has it’s pros and cons.

I’ve recently been faced with a major life decision: do I make Amsterdam my home base or carry on traveling? While considering the pros and cons of each, I became acutely aware of the contrasting desires I have. I thought I’d take this opportunity to let you inside of my head, and share the many thoughts I’ve battled with while navigating which direction to take my life in. Every digital nomad will, at one point or another, ask themselves one question: do I carry on as a nomad, or become a settler? This is the digital nomad dilemma.

In Favor of Settling

Thoughts of settling down somewhere or even buying a house have crept into my mind. And I guess I have Corona to thank for that. It halted me, it halted the entire world, long enough to find that I actually enjoy the stillness and a routine.
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I have hopped around countries and continents so quickly that it all just kind of blurs together. The Netherlands, where I’m currently writing from, is my 51st country. Digital nomad life has been wild, and I never thought that it could be anything short of spectacular. Until now. Maybe it’s biology or my age (I’m 33) kicking in- but recently I’ve found myself wanting more stability. Thoughts of settling down somewhere or even buying a house have crept into my mind. And I guess I have Corona to thank for that. It halted me, it halted the entire world, long enough to find that I actually enjoy the stillness and having a routine. Here are some of the thoughts I’ve been having recently that are very much in favor of settling:

  • I want a beautiful space that’s all my own. I want it to be full of light, and inspire my creativity.

  • I want to the comfiest L-shaped sofa. And candles. And the softest blanket I can find.

  • I want to fill a kitchen with cooking essentials, and actually enjoy learning new recipes.

  • I want to hang all of my clothes up in a closet. And buy more clothes than my suitcase could ever handle.

  • I want to stock up on ALL of the wine, and have a fancy set of glasses.

  • I want to take fitness classes multiple times a week, and get into the best shape of my life.

  • I want to date, without the pressures that come with either leaving soon, or staying to see if it can work.

  • I want connection. In the form of a significant other, and a close-knit group of friends. I want late nights and laughter with these people. 

  • I want to be a “regular” somewhere, and see familiar faces in my neighborhood.

  • I want safety. And I want to manage the anxiety that I honestly might only have BECAUSE of traveling so much.

  • I want the ability to explore lesser known parts of Europe without worrying about a visa and time running out.

  • I want to start my own side hustle, and have time to focus on building something profitable and meaningful instead of always planning my next move.

And JUST when I think I’m comfortable with pursuing options that would offer me that….I have a panic attack, and thoughts come flooding in that are:

In Favor of Traveling

I hear Spanish music and my heart physically aches for South America. I see a Thai restaurant with some silly name like Sawadee Ka and I’m transported back to Thailand- chasing waterfalls or winding through traffic on the back of a motorbike taxi in chaotic Bangkok.
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My biggest fear is that in choosing a home, I’ll be giving up all of the wonderful things I love so much about traveling. I hear Spanish music and my heart physically aches for South America. I see a Thai restaurant with some silly name like Sawadee Ka and I’m transported back to Thailand- chasing waterfalls or winding through traffic on the back of a motorbike taxi in chaotic Bangkok. Every memory hits me like a ton of bricks and the nostalgia is so bittersweet. These experiences, and the way they make me feel, are addicting. I crave them, and after a few weeks in one place my feet get itchy. Here are a few of the things that make me want to pack up my bags again and never look back:

  • The rush that comes with arriving in a brand new place and having absolutely no idea how anything works or where anything is.

  • ….Followed by the sense of accomplishment that comes from figuring out how everything works and where everything is.

  • The constant exposure to different cultures and types of people.

  • Never getting bored and the thrill of the unknown. What country will I be in next week? Who knows!

  • Airbnb hunting (it’s my favorite activity) and getting to try out all different kinds of homes.

  • The ability to choose cheap countries and save a lot of money.

  • The amount of friends I’m able to make from all over the world.

  • The stories. I just want to keep compiling stories.

  • The freedom. The ability to go where I want, when I want is an incredible gift.

As you can see, this list is a bit shorter than the first one. I see so much value in traveling full-time and having a base, but if ever there was a time to enjoy a more settled life, now is it. If 2020 has taught us anything, it’s that our health and safety are everything. Carrying on as a traveler feels not only risky, but a bit insensitive as well. So when things normalize, Europe will be my playground. It will be a different kind of life, and a different kind of travel, but one that I think I’m ready for, and honestly, am really lucky to even have.

And guess what. Even if I COMPLETELY change my mind in six months or a year- nothing is permanent. But right now, my heart says stay still. Be more intentional. And that’s what I’m going to do! So if there’s anything you want to know about life in Amsterdam, do let me know, and I’ll make sure to write about it! :) Also, if you’re a nomad and this resonates with you, I’d love to hear about it!