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How I Tested Out the Digital Nomad Lifestyle at Home Before Taking the Plunge

By Landing | Nov 23, 2022
Landing member Gregg Congrove snowboarding.

This blog is a guest post from Landing member Gregg Congrove.

Last summer, I was vacationing in Hawaii, and toward the end of the trip, I found myself wanting more. I wished there were a way I could stay longer and be able to explore the area and spend time getting to know the island and its culture, hiking, and seeing the scenery without having to rush through everything in just a couple of weeks. 

When I returned home to Texas, I began to hatch a plan to free myself of the anchors that prevented me from really traveling the way I wanted to. I would need to get rid of my house, get rid of the mundane belongings I’ve collected over the years, and figure out how I could travel the country without going broke. 

Here’s my story of how I dipped my toes into the digital nomad lifestyle before fully committing—and why I ultimately decided to take the leap. 

Catching the “nomad bug” 

I have been working remotely in IT for about 10 years, so I’ve become comfortable with working from the road, in hotel rooms, and even on ski lifts in Colorado (noise-canceling headphones are a must-have!). 

I’m also into overlanding, which is basically just traveling by land. I have a 4Runner that’s decked out with a rooftop tent, refrigerator, and solar panels, so I can live (and have lived!) off-grid for weeks at a time while continuing to work. I just need a solid internet connection, which can often be a challenge in itself. 

As I thought more about how I wanted to travel, I realized I just needed to “live” in the places I wanted to visit. But first, I had to do something with my house in Texas. It was holding me back and anchoring me to a single location. I didn’t want to have to pay my mortgage on top of the housing costs I’d pay to stay somewhere else for a few months. 

I considered selling it as the housing market blew up, but ultimately decided to keep it as an investment property and rent it out. I then sold or donated the majority of my belongings, keeping only some clothes, my laptop, a few electronics, and, of course, my snowboard.

Next, I needed to figure out where I was going to live. I needed something inexpensive and fully furnished. I found myself in the same predicament of being stuck with “rent,” (albeit cheaper than my mortgage) for a home that I would be spending very little time in. But then I found Landing, a network of fully furnished apartments across the country that provided short-term leases and only required a two-week’s notice to go somewhere new. This really caught my attention. I didn’t even know this type of thing existed!

I wanted to take the plunge but I was nervous to make such a drastic change to my life, so I decided to start out slow. I put my house up for rent and moved into a Landing that was located in the same area I was living in. It was the same scenery I have been used to, but I wanted to make sure that if the Landing situation didn’t work out and I found myself homeless, I still had friends and family in the area as a backup plan.

The Landing team was extremely helpful and communicated with me every step of the way. This really helped ease my nerves and gave me confidence I was making the right decision. On moving day, I was greeted by my host who gave me the keys, showed me to my new home, and gave me a tour of the complex and its amenities. I was able to load everything I owned into my 4Runner and even managed to get it all into the Landing with just one trip using a luggage cart. If I’m being honest, I still have a little too much stuff, so I’m going to try to purge some more before I move again. Living with Landing makes traveling light super easy. The apartment has everything I need. 

It’s been just over two months and I’ve been in two Landings in my home city. My plan is unfolding perfectly, and I’m ready to start traveling and actually living in new places, not just visiting them.

Making it happen 

I’m really excited to start this journey! At the end of December, I have my first out-of-state Landing booked. I’ll be packing up my 4Runner and driving up to Utah. I’m staying in Salt Lake City, which will be a short drive to Park City, where I plan to do a lot of snowboarding! I already have family and friends lined up to come visit, too. We will be hitting the mountain, visiting Zion National Park, and probably doing some camping in the 4Runner. I plan to stay there until sometime in February.

It’s too far in advance to plan out my next destinations, but most likely I will hit California during the summer so I can be by the coast and do some surfing. I’ll probably stay for about two months before hopping to the next city. I’ve already started making a list of all the states I’ve been to and the ones I still need to visit, eventually I would like to say I’ve spent time in all 50 states. 

What I’ve learned so far

For anyone considering a digital nomad lifestyle, my recommendation is to just do it. Too many people get caught up in the planning stages and end up getting analysis paralysis. Too many what-if scenarios keep them from living their dreams. People are actually really good at adapting. Just jump in and do it! Tackle any issues as they arise. Landing has you covered with their fully furnished apartments and wonderful customer service. Your hardest decision will be where to go next.

I’m still at the beginning of my journey. But I’m happy that I’ve found Landing because it’s given me the opportunity to spend more time traveling without breaking the bank.  


Ted may be the world's slowest typist and struggle to hold a pen, but he has mastered how to pursue a more flexible lifestyle throughout his airborne adventures around the U.S. Whether you're looking for more information before migrating to a new city or want to find an easier way to rent a nest—erm, apartment—Ted will always be here to share his best advice for where to live and how to thrive.