How Life Led Me to Be a Digital Nomad and Travel Writer

Hi, I’m Jess.

I’m a New Hampshire native, I’m just shy of 30, and as much as I love to travel, I’ve never lived outside of New England. This October, I’m setting out to fulfill my dream of traveling from city to city across the United States. I’ll be visiting Nashville, Austin, New Orleans, and many more cities to try the best food and drinks, hear all the live music, and discover the best-kept secrets you can’t find on Google.

And the best part: I’ll be writing about my experiences to give other Landing members an idea of what it’s like to live nomadically and how to enjoy each city to its fullest.

But first, how did I get here?

Born to write, but not to travel

I’ve always loved writing, but I haven’t always loved traveling. I never had much of a desire to leave the comforts of my home state of New Hampshire. Plus, I had (and still have) a crippling fear of flying.

When I went to college, I simply picked my state university without even looking at any out-of-state schools. But, during my sophomore year, a close friend of mine asked me to study abroad with him in London. 

London? Like London, England? On the other side of the Atlantic Ocean?

I didn’t think I could do it. The farthest I’d ever been away from home was when I went to Florida with my family. They all eagerly hopped in line for the tallest, steepest roller coasters at Universal Studios while I squinted against the sun to count how many more rides it would take before it was their turn. 

My palms began to sweat at the thought of a seven-hour flight to London. But my family was insistent that I should go—It was a once-in-a-lifetime opportunity. So, despite all the alarm bells going off in my head, I agreed to go. And that changed everything… 

Living in London for four months completely opened my perspective on life. 

I got to meet so many people from all kinds of backgrounds, visit historic landmarks I’d only ever seen in movies, and create memories that will stay with me forever. When the end of term rolled around, I didn’t want to go home. I just wanted to keep adventuring, to try the rustic pizza in Italy, drink the huge steins of beer in Germany, and swim in the Mediterranean Sea.

But alas, I went back to my cozy little New Hampshire town and finished earning my degree. That was the smart thing to do, right? I told myself that after college I would start traveling the world. 

Living out the smart choice

My senior year, I got an internship with a small startup company in Portsmouth, New Hampshire. It was a really great opportunity that helped prepare me for the “real world.” When graduation rolled around, the company offered me a full-time marketing position.

Yep, you guessed it. I stayed in New Hampshire and settled into my responsible job and one-bedroom basement apartment. Womp womp. I put my travel dreams on hold, figuring I’d only work there a little longer. 

Spoiler alert: I worked there for over four years.

Before you groan, it wasn’t that bad! This company knew how much I loved to travel, so they sent me to conferences and company meetings all over the U.S. and Europe. And, I would often extend my trips and do some solo traveling. When in Sweden, right?

I got very used to traveling alone, despite the look of horror on everyone’s faces when I told them that yes, as a young American woman I was traveling by myself. If you think it’s scary, then you’ve probably never tried it. It’s pretty liberating. Think about it—you can do and go wherever you want, rather than being stuck eating McDonald’s again, because your friends think the local food smells funky.

So, even after visiting 13 countries, making endless, nameless friends, and overhearing way too much snoring and partying at crammed hostels, I still felt like I was missing out on something. Whenever I visited a new place, I felt like I was only just getting to know it before *poof* I was back on a flight home to New Hampshire, usually chatting the ear off of the poor passenger next to me to keep me from hyperventilating. 

I wanted to visit cities for more than a long weekend or a one-week stint. I wanted to really get to know the locals, try the funky-smelling food, and find all the best spots to go to—not just the ones I could find on Google. But thanks to job commitments, long relationships, and a laundry list of other excuses, I found myself staying in New Hampshire for a few more years.

And then 2020 happened… 

I was working in a controlling, toxic work environment located in (once again) Portsmouth. As soon as the pandemic hit, I got laid off. Yay?

In the end, it was a “Yay!” but it took me a little while to get there. 

After dealing with the typical unemployment woes and feeling sorry for myself, I finally kicked my butt into gear. I had to.

Honestly, you can only watch Netflix and talk to your cat for so long before you start to crave actual work and responsibilities.

So, I did what my career had trained me to do. I started my own freelance marketing business… In the middle of a pandemic… When businesses were all closing… Great idea, Jess.

But hey, you miss 100% of the shots you don’t take. Didn’t Michael Scott say something like that?

In 2020, I turned all my boredom and sadness into motivation to become self-sufficient. I didn’t want to go back to a typical office setting, and I wanted the freedom and flexibility to work on my own terms and my own schedule. In the back of my mind, I knew this would allow me to travel how I wanted to, but I didn’t want to get my hopes up just yet.

So, I started by building up my clientele. And by that, I mean I reached out to nearly every business within a 50-mile radius, begging them for work, even offering to work for free at times. Listen, I was desperate.

But finally, I got my first client, which was kind of cheating because I used to work for them down in Boston. Honestly, I would’ve taken anything, though. But then I got my second client, a cute little coffee shop in town that desperately needed to draw in customers. We started a newsletter together and began drawing in a crowd. And then I got another client, and another. Soon enough I went from working two hours a week to working 20 hours a week. I became my own boss, and I liked it!

Time for the reckless choice

Once the pandemic started to subside, I began planning the next phase of my life—the one I’d been fantasizing about ever since I stepped out of Heathrow Airport. It was finally time to focus on myself and make the reckless choice for once.

I started planning my route. Being a New Englander, I’d already seen most of the upper East Coast, and I knew I still wanted to stay close to the ocean. I figured out I wanted to at least go to Nashville, Savannah, New Orleans, Austin, and somewhere in Arizona, California, and Washington. That about covers the coasts.

Next up was figuring out where to live. It’s just me and my cat, Blink. We don’t need much. Just a one-bedroom apartment in a nice area. That allows cats. That offers month-to-month leases. That’s within my budget. Oh, and if it could be furnished too? That would be great, thanks!

Yeah. Not so easy to find.

After scouring Craigslist, Apartments.com, and even Airbnb, I had no luck. All I found were scams, 6- to 12-month leases, and fees, fees, fees. Sigh. I was SO close to finally living my dream. And now I’ve got this one stupid, teeny-tiny, GIGANTIC roadblock because I don’t know where I can live.

And then suddenly, a Google ad popped up for this company called Landing. It was the perfect option for remote workers with wanderlust. They offered luxury apartments with flexible leases in major cities across the country. And they allowed pets! Tick. Tick. Tick. Tick. 

Hello, Landing!

On top of everything else, they were a new company. They’d only just started in 2019, and they were trying to grow their online presence. I thought, “What if they could use some writing help?” I did some sleuthing and found that their Content Marketing Manager, Bri Hand, lived just one state over in Massachusetts and was also a UNH alumnus. Hello, fate!

I reached out to Bri, and she answered me right away! A fellow UNH alumnus? Who loves to write? Who is traveling around the country using Landing? She was sold. She asked me if I would be interested in writing blog content for them about the experiences I’ll have in my travels. Pinch me, I’m dead…

The next step was figuring out where in the world (literally) to start. 

Where to begin…

I recently went down to Nashville, TN, for a short trip, and I absolutely fell in love. I met the nicest people (women literally stopping me in the middle of the bar to tell me they loved my outfit) and had SO much fun going up and down Broadway every night. The hot chicken and fresh biscuits were better than I had ever imagined, and there was so much fascinating (and haunted) history everywhere. 

But most of all, I loved the live music. 

After being indoors for nearly 18 months, the thing I missed most was live music. So, what better place to visit than the Music City itself? 

On my short visit, I quickly found out that wherever you go in Nashville, whether it’s a bar or a boutique, day or night, there’s someone strumming a guitar singing classic Dolly Parton tunes. I couldn’t get enough of it. As soon as I found out Landing offered apartments in Nashville, I was hooked.

So now I get to finally pursue my dream of traveling while doing my dream job of travel writing. I couldn’t ask for a better opportunity. I’m going to finish reading “Eat, Pray, Love” real quick, and then I’m on my way!

My journey begins in Nashville this October, so follow along as I share the best things to see, eat, drink, and enjoy wherever life takes me.