A 2-Year Reflection on My Digital Nomad Lifestyle

Dianna Allen

Or two years professionally homeless, as James Ivings would say. Potato, tomato, right?

The memory of purchasing your first one-way ticket never disappears. At least, not for me. To decide that you want to start a new chapter in life, throw away the past, and go full-force towards a dream… you almost feel invincible. The rush of adrenaline and excitement over the unknown, it’s a feeling that can’t be replicated. And every year on August 29, I get to relive that fond memory from two years ago; if only for a moment.


In the past two years, I’ve started from scratch and pushed myself to provide by utilizing digital skills in almost every way possible. I’ve traveled to and lived in 10 countries. My wardrobe has diminished quickly from filling a closet to 2 suitcases to 1 carry-on. I’m also more social than ever, with those who I’m lucky to call real friends nearly tripling in quantity.

Some bad things have happened too. I lost 20 pounds, bringing me to (what I feel is) the most unhealthy weight I’ve ever been in my adult life: ~90lb/43kg. I had food poisoning once, I was constantly sick traveling through Asia, and I had moment of severe insecurity, self-doubt, and the overall feeling that I ‘lost’ who I am as a person. There was a period where I would cry almost every day, feeling unsure about whether this should be my life or not.

But, what I didn’t realize then was that I was mostly dealing with growing pains and the struggle of adjusting to a whole new lifestyle. There was no easy transition — I simply left all I knew one day and ended up in a whole new life the next. What was once 7am alarms, driving to work, and relaxing with Netflix during the evening, was now waking up whenever I feel like it, working whenever I feel like it, and relaxing… well, whenever I feel like it!

You may think that sounds like a dream, but I didn’t live for the weekends anymore. In fact, it was quite the opposite. I lived for the weekdays. I’ve never had so much freedom in my life and all I wanted to do was create. I wanted to bring every single idea I had in my mind to life. But because I wasn’t disciplined with myself during those tough times, there was no progress and I was left feeling unfulfilled. Which brings me to the first point of focus I’d like to talk about…

Career and Personal Projects

When I first left the states to travel, I allowed myself 1 month of no stress. To just live and not worry about work. Once that month was up, I jumped into the first skill that I was aware of having. This was copywriting. For the next 6 months, I found myself struggling to make ends meet with this. While I did earn money, it was not enough to survive.

On the sideline, I also wanted to create a personal project, for fun and with hopes of making some dollars from it. With this in mind, Outglobing was born. Some of you may remember it — it was my travel blog. With fresh eyes and the unknown world within my reach, creating a travel blog was only logical.

Fast forward, almost a year later, I needed to rethink how to make more income. So, I taught myself illustration. It all started with the infamous Dwight Schrute illustration. From there, I began actively searching for graphic design jobs. Logos, banners, vectorizing raster images, label and packaging design… anything to do with Adobe Illustrator and Photoshop, I was determined to succeed.

Eventually, I landed a label and packaging design project. Instantly, I was in love. I’ve always been the arts ‘n crafts type of person, so much that I used to have a bath and body business that sold handmade products. Oh, how I miss being able to create those items, and creating packaging designs brought me to fill that void.

So, I told myself that I would specialize in packaging designs. Since then, I’ve worked with a salsa company, numerous bath and body brands, and my biggest client yet is a newly launched hair care brand. If you would have told me 2 years ago that this is what I’d be doing now, I’d laugh and say ‘I wish’.

Somewhere in between all of that, I also learned how to code. In fact, I completely re-developed Outglobing to put my new skill to the test. I removed my personal perspective and instead offered unbiased destination guides. Learning to code came quite easy to me, and I actually ended up selling that entire project for nearly $400. Not bad, considering it had generated $0 in revenue and I had lost interest to continue after a while.

Which brings me to what I’m doing now; Budget Meal Planner. That’s a long story and I’ve told it time and time again. So, you can just listen to my Indie Hackers podcast episode if you want to know the details of how that all began.

Reflecting back on this aspect of my life, it certainly seems that I was all over the place. And well, I was. For nearly 15 months, I was really lost with what I should do, what I can do, and what do I really want to do. It took a lot of time and a huge kick in the ass by my loving boyfriend, but I ended up finding myself (in this aspect of life) after all.

Family, Friends and Love

In the first year of being abroad, my main concern was maintaining my relationships. My dad wasn’t exactly on board with my decisions, my mom missed me like crazy, and my friendships were becoming stagnant because I wasn’t around anymore to nourish them.

But throughout it all, my friendships have become stronger, so much that I even was able to mend a lost friendship. I’ve also learned to become more social. I have friends all around the world now, real friends that I actually want to hang out with, and it’s so comforting.

My mom can handle me being away now, and my dad still isn’t approving this lifestyle I’ve chosen, but he has now accepted that this is happening and I won’t be moving back home anytime soon.

But what stands out the most in all of my relationships is my boyfriend. We’re from different countries, and because of this we seem to be stuck in a loop of traveling around. Neither of us have permanent homes and we’re barely allowed in each others home countries for more than 90 days; so where do we go?

We obviously don’t want to be separated, but we’re beginning to feel that the travel bug that bit us a couple years ago is fading away. We’re approaching our 3rd year of being digital nomads together and with visiting my home in the states and possibly Mexico on our list, we will have experienced most of where we’d like to go.

It’s a tough situation for the future, when we do want to stay somewhere more long-term, but for now I am thankful that we make this work.

It’s very eye-opening to see the struggles of being in an international relationship and how simply holding different passports affects where and how long we can be together. How unfortunate…

Health and Self-care

Self-care has been a hot topic for 2019, for good reason. We’re becoming more aware of ourselves and what we’re neglecting. For me, this was mostly finding healthy hobbies. Since my lifestyle drastically changed, the things I’d normally do, weren’t realistic anymore.

I can’t sit in my kitchen and craft bath bombs for fun. I can’t adopt a cat and have her join me in my travels. I can’t attend my favorite hometown sports games. And I certainly can’t go on Target runs or join my friends when they want company to take care of errands for the day.

I’m proud to say I’ve recently discovered Stardew Valley for when I’m bored at my laptop. I enjoy working on Budget Meal Planner and growing it in every little way possible. I spend more time talking to friends and family these days, I even use FaceTime every now and then. Dianna 2 years ago would never in a million years do that — phone anxiety is real and I suffered with it until early this year.

Sports games and Target runs have now been replaced with spontaneous activities (like tango dance lessons) and casual outings with new friends found from the internet.

Traveling long-term is not climbing mountains and sight-seeing every day of the week. In fact, I usually reserve that for the weekends or when I have more company around to enjoy the day with. My life abroad is still quite normal and I think for me, that’s what I need to maintain self-care.

My health took a hit the first year of traveling. I’m not sure why, but in Asia I was sick nearly every month. It was always a simple cold, but it’s unlike me to ever feel under the weather.

And as much as I loved eating all the foods in Asia, I also had periods where I never ate anything because I was in a such an isolated town. I never cared to book Airbnb’s with kitchens because Asia is known for eating out. Cooking inside is weird! But, I never thought it’d be an issue.

Onto year 2 of traveling through Europe, everywhere I stayed had a kitchen. And I didn’t mind cooking most days. I felt healthier and it was cost-efficient at the same time. Plus, I never got sick in Europe, not even allergies. Well except for that time I housesat and watched over cats. I know I’m allergic to them, but I also love them that much.

Now approaching year 3 of the digital nomad lifestyle, I’m heading back to Asia. But I’m putting my health first. All booked Airbnb’s must have a proper kitchen and I’m only allowing myself to eat out once a day, and only for a delicious quality meal. I simply can’t eat a fried omelette and rice for breakfast every single morning again, even though I do find them very tasty.

There’s a lot I’ve learned about myself the past two years and the most important has been what factors make me the most comfortable. This directly affects my mental state. Just because I’m traveling doesn’t mean I have to lower my standards. I still need a washing machine, full kitchens, and a proper queen-sized bed. I also enjoy the luxury of big kitchen tables to spread out my tech setup and endless notebooks. Netflix, a comfy sofa, and a large TV for lazy days is also a must.

I probably sound high-maintenance, and perhaps that’s the curse of being born to a first-world country. But, at the core of who I am, I am an introvert. I want to be left alone most days, with loud music blaring through the rooms. I don’t want to be in co-working spaces, I don’t want to sit in cafes… I guess I’m just longing for the feeling of a home regardless of where I am.

FOMO (Fear of Missing Out)

Would I be lying if I said I never feel it? Absolutely.

FOMO doesn’t come around often, sometimes it doesn’t show up for months, but holidays, birthdays, and once in a lifetime celebrations (*ahem* St. Louis Blues winning the Stanley Cup — HELLO!) really can hit hard. But thanks to social media, and my most kick-ass friends, it really doesn’t feel so bad.

When the Blues won the cup, anyone and everyone from St. Louis wanted to be at the Market Street parade, and my heart was hurting that I couldn’t be there. But, my wonderful friends FaceTimed me during the celebration and those little reminders that I’m loved and being thought of make all the difference.

So, yes, I do get FOMO while traveling… but I’m not missing out.

Travel and Culture

It’s ironic, this is a topic I feel that I have the least to say. It’s because I adjusted to this easier than anything else, and that could be because travel was the one thing I was expecting to be difficult.

But, it’s not. Traveling has been the easiest part of this entire new chapter of my life. I know it’s because I’m lucky to have a strong passport. I understand that every day I’m able to easily navigate to and in a foreign country is because I won a lottery, and I do not take that for granted.

I admire all the cultures I’ve been able to experience. I don’t look down upon anyone, I try not to get frustrated when things don’t make sense, and I do my best to be as respectful as I can. And I think patience and understanding has been the biggest lesson that’s come from all of this traveling.

Also, that we are all exactly the same. I’ve learned from all the people I’ve met and watched, that we’re just doing what we can to provide for ourselves and others. We enjoy honest conversations and simple smiles when passing each other on the street. We want to be respected and not taken advantage of.

Traveling has taught me a lot the past two years; many uncovered details about myself that I wasn’t aware about and the truth behind the rumors and lies that are being told daily about other countries.

Like, Asians can’t drive? Who the fuck started that? I applaud Asian drivers — their skills are unmatched!

Photo by Anete Lūsiņa on Unsplash

Dianna Allen

Written by

I wear many hats: Branding and Packaging Designer, Creator of Budget Meal Planner, Berry Farmer at Stardew Valley. From STL.

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