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Lessons from My First Year as a New Digital Nomad – Sell It All!

One Year Ago I Sold My House And This Whole “Experiment” Really Got Interesting

Every time I feel like I’ve expanded my comfort zone to an extent I never imagined I could, I’ve ended up finding a way to push it even more. I guess that’s what happens when we “do the work” to challenge ourselves beyond our own self-imposed status quo. We really do end up growing, and typically more than we could have imagined. The past year—stepping out into a life of travel—had so many lessons learned, humble and uncomfortable moments, beautiful exploration, and reflection. 

Thanks for signing up for this look back through my first year as a true, no-strings digital nomad. I learned a lot. Here are just a few of the lessons learned and takeaways. Click through to the full lessons from each part if you want to know more!

But first, in case you’re new here or just want a refresher, here’s a little back story on how I ended up here. The real “Nomad Experiment” started a couple years ago, but none of us are without foundation. Here’s mine, before we get into the goods. 

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Part 1: The Backstory – Life Before Digital Nomad: From 0-41 years old

Let me get you quickly up to speed on the past 41 years leading up to the day I sold my house and cut my last “location dependent” strings. Well, at least the “adulting” parts I can remember. I had rented about half my adult life and owned (the mortgage to…) my 1100sqft home for the other half. Been employed at small design firms about half and modestly self-employed/freelance for half.

I was rediculously in debt (over $50k at one point) for about half and have lived completely debt free, other than a mortgage for half—after spending 4+ years digging out of course.

And just a couple years ago, at age 38, I had only been to about 20 US states and to two other countries outside of the U.S. Only Canada and the UK. Spoiler alert, by the time I sold my house a year ago, I had only made that about 30 states and 3 countries.

Travel—especially the idea of nomadic travel—wasn’t something I knew through the first part of my life. Truth be told it’s still pretty scary to me, learning by doing…solo.

At 39 I realized that thinking and conjecturing about travel and what my life “could look like” wasn’t cutting it I bought a one-way ticket to Mexico. Seemed like the logical thing to do? I had thought about becoming a “digital nomad,” but I needed to test living out of a suitcase while working regularly in a country that I didn’t know. So I tried it, and ended up spending 3 weeks bumping through Mexico by bus. Flexing the upper and lower ends of my emotional spectrum the entire time.

There may have been at least one phone call to my mamma back in the states with some ugly crying and the question “What the f*ck am I doing with my life?” uttered on repeat…

That’s it. I’m Done With Homeownership…At Least For Now

After a couple of years of really testing and pushing what I had only dreamt about, I finally snapped on homeownership a few days before my 41st birthday.

I finally got fed up with all of the responsibilities and extra costs that offset the pleasant parts of homeownership. A life of travel was what I wanted at that moment, so these things just didn’t fit anymore…at least for the time being.

An impending new $15k HVAC system and $10k of exterior routine maintenance need definitely helped that decision. I chose to be done with it, dealt with repairs and all the joys of selling a home, and finally handed over the keys to the happy new owners. I then spent a couple of days saying some goodbyes, enjoying time with friends, then hit the road.

The Beginner Traveler's Guide Nomad book cover

Truth Time: About my “Sabbatical”

Let’s stop for a second for a side note about my self-imposed sabbatical. I had reprogrammed my life and client base a bit in recent years so that I was more flexible in what work I was taking and where I did that work. Therefore I had planned to take 6 months “off” from client work once the house was sold.

In actuality, I would use some of the small proceeds from the house sale to live off of while not getting paid. I would shift my 40+ hours a week of work to The Nomad Experiment.

Shooting and editing videos as well as writing. I really want to make inspiring others through writing and video my “full-time” job, so I wanted to make that my next big experiment. Heck…maybe even write a book. I wanted to see what could happen, and how it felt, when I concentrated on this full-time for at least 6 months. OK. You’re up to speed! Now on to my first year as a true digital nomad…

Note that this page has all of the top lessons if you read on, or you can jump to the specific article for more first-year digital nomad nuggets and lessons. (I really just wanted to say “nomad nuggets”…)

Part 2: My Great American 2-Month U.S. National Park Road Trip

After I sold my house I hit the road in the U.S., destination west coast, with about 2500+ miles and a handful of National Parks in between. I camped and slept in my Jeep most of the trip. Often learning how to find free “boondocking” spots to overnight in National Forests, or less lavishly, Cabella’s parking lots. I published nearly a dozen videos and a few written pieces and visited 8 National Parks over that span.

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The Biggest Takeaway From My 2-Month Road Trip Across The U.S.

The U.S. is big. No really, really big! It’s extremely hard to understand quite how big it is until you drive it. I feel like the ability for us to fly coast-to-coast- in less than 5-6 hours has created a pretty jaded idea of the size of the U.S.

It’s about 3,000 miles —about 50 hours at 65mph—from New York, NY to San Francisco, and that’s without looking around or stopping to pee!

As a solo overlander trying to balance being a digital nomad, the amount of time spent with my hands on the wheel was daunting. Luckily I always have the voices in my head to keep me occupied!

Read more about that 2-month road trip across the U.S. and more lessons and takeaways by clicking here.

Part 3: 2 Months Hunkered Down & Being With My GrandFather As He Passed Away

I then planned to spend two months hunkered down working on editing video and writing, starting off with friends in Michigan. While I was in Michigan my dad texted me and said I probably need to get back quickly since my Grandfather had taken a turn for the worse.

An hour later I was packed and in the Jeep and driving back south. Helpful bonuses of being a digital nomad; traveling light and being able to adjust quickly.

Understand that as a true nomad with no roots, you can still choose to nomad where you once planted roots. I have amazing friends that I spend weeks with now when I’m back in Charlotte, NC. I also now have the freedom to spend extended amounts of time anywhere in the world with friends that I used to only see once every few years.

My grandfather passed away about a week later with my dad and me at his side. By the time I got there he was fairly unresponsive and hospice came soon after.

That week was mostly spent in memories and conversations from friends, family, and nurses from his retirement home about his amazing smile, laugh, and hugs. The man gave amazing hugs.

Now that I think of it, maybe that’s where my love for hugs originated. I learned a lot of lessons about life that weren’t part of my plan. But you know what they say about making plans…

digital nomad life lessons grandpa jason

The Biggest Takeaway from being bedside when my Grandfather Passed

As a person who likes words, I realized that sometimes words aren’t necessary. Just being present is.

My Grandfather was my Pop’s best friend, quite literally. They had spent more time together in the past 5 years than since my Pops was a kid. My Grandfather was also a huge part of my life and a massive impact on the man I am.

He taught me to cook, garden, work hard, respect women, and hold my tongue (sometimes), among countless other things.

I had never been bedside for anything like this and didn’t really know how to be or act or help. But just “being there” seemed to be enough for my Grandfather and my Pops. Words aren’t always necessary, and there are obviously things that words simply can’t fix. 

Read more about those 2-months and more lessons and takeaways by clicking here.  

Vienna Austria Votivkirche Neo Gothic Cathedral The Nomad Experiment Photo
Votivkirche Cathedral in Vienna Austria

Part 4: 2 Month Traveling Across Europe, and Getting a Tooth Pulled in Budapest!?

When the year started I had been to 3 countries outside of the U.S. This trip would add 7 within 2 months: Ireland, Hungary (Budapest), Slovakia (Bratislava), Austria (Vienna), Czechia (Prague), Germany (Munich), and France (Paris). (Here’s the video playlist…) I even saw a church full of bones!? I’ve never really aspired for “numbers” as it came to travel. But with that said, it’s amazing in hindsight how I expanded my understanding of places in the world so quickly by traveling to that many in a short amount of time.

I stayed at 14 hostels along the way, the most memorable being in an empty hostel on the Aran Islands off the coast of Ireland…for 3 only $25 a night. I love hostels and it’s where my mind really opened up to amazing, inexpensive yet awesome travel in my late 20s.

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My Biggest Travel Lesson From 2 Months As A Digital Nomad In Europe

Pride is a Sombich’—Go with your gut! The seven weeks of travel in Europe leading up to my week in Paris, there was major chatter of a complete transportation strike.

That full Paris transportation strike was scheduled for three days before my flight back to the U.S.

I continued to track it and bounce back and forth between just chancing it or spending the money to change my flight to before the potential strike. With CDG airport being about a 1.5-hour rigorous public transit trip from central Paris, I chose not to chance it. I paid the $100 and I flew home the day before the strike instead. The next day the city shut down…for over 6 weeks of sweeping transit strikes and protests.

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The “inconvenience” to me of changing my plans was minor but, had I not, I could have had real problems getting home at all. Pride was also involved, since I had this idea that a seasoned traveler would just take it in stride. But that was silly. I am me, and I needed to do what was right for me. And that was the right decision nomatter how it panned out.

Read more about those 2-months of travel through Europe as a digital nomad and more lessons and takeaways by clicking here.

wall map travel video
hiking video connemara national park ireland the nomad experiment

1.5 Months hunkered down in the U.S.

I spent roughly the next month and a half hunkered down around Charlotte. Sometimes renting a spot with friends, sometimes house-sitting. Shooting and publishing a lot of videos and catching up on some writing.

I also ended my sabbatical and started doing client work again, since depleting the savings was not a sustainable long-term plan.

I had given myself 6 months, and per my typical rule-following protocol, it was time for me to start making the donuts again. Now it was really time to learn to be a digital nomad and actually make a sustainable living while enjoying the ability to travel. 

Part 5: 2 Months of Slow Travel: Living and Working as a True Digital Nomad in Queretaro, Mexico

The previous 6-7 months may have resembled a mid-life crisis, but not really since it was quite calculated. I definitely took advantage of the severing of my previous “strings-filled” life as an opportunity to check off what I once viewed as “once-in-a-lifetime” bucket list travel goals.

But one thing I know about myself is that I don’t like fast travel. I like slow, methodical travel where I can experience and absorb and not wake up exhausted. 

So I knew that, while getting back to paid projects and clients, I wanted to go “live” somewhere outside of the U.S. for a couple of months and absorb. Yes, a bonafide digital nomad slow travel life. After my first few trips to Mexico, I knew I loved the people, the culture, the pace…and especially the food! So after much deliberation, I spent the next 60 days staying at long-term Airbnbs in Queretaro, Mexico, and the region.

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One Big Lesson From Living As A Digital Nomad in Queretaro, Mexico For Two Months

The overwhelming majority of people…like everywhere…are the same. At the root, they just want to love and be free to love, protect their family and loved ones, and live a good life. They smile and hug and care. This isn’t a new revelation at all for me, but it continues to be proven with each new turn on this whole experiment. Now, the governments and their offices, politicians, and agendas may be a different story.

Read more lessons and takeaways from those 2-months of travel, living and working as a digital nomad in Queretaro, Mexico by clicking here.  

Part 6: 2 Months Back in the U.S. During the Beginning of the Covid-19 Pandemic

Let me just disclaimer this by saying that I literally can’t begin to understand the hardships that Covid-19 is causing so many people. I just wish it wasn’t happening. The whole reason I want to travel is to open my mind and heart to more people around the world. But the fact that I have the luxury to come back to my relatively “safe” space back in the states is bittersweet. It’s not fair, and I truly have no idea how to grasp it. But with those understatements said, it has caused me to take these two months to find some important thoughts.

One Big Takeaway From The First 2 Months During The Covid-19 Pandemic

We need to take as much control of our days and years as we possibly can. Pandemic or not, choose the scary and uncomfortable paths that bring us the possibility of adding true depth to our lives. Try our damnedest not to allow ourselves to fall into a status quo. Challenge ourselves to grow and push outside of our comfort zone on a regular basis instead of becoming complacent and allowing months and years to pass without true growth.

Realize that life is long if you pack more life into it. But when you put it on cruise control, it shortens by default.

Choose to pursue the unknown, knowing that you can always go back to what you know or what you’ve done in the past. If you love where you’re at and what you’re doing, then by all means, keep doing it. But if you’re one of the overwhelming percentage of people that are generally or regularly unhappy with where they’re at, change it!

It likely won’t be comfortable or easy at all turns.

But I can tell you from experience that you’ll at least feel like you’ve lived life instead of feeling like you’ve sat and watched it pass you by.

Click here for more lessons from the first couple months of the Covid-19 Pandemic. 

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Jason Vagabond Shirt Nomad

Parting Thoughts on my First Year As A Digital Nomad

Wow. Here’s the thing. I hope that if you follow any of my writing or content before this that you understand that my main goal is growth. Growth personally and growth for you and others by somehow turning my experience into something you can use. I know that travel will help us grow, and travel was something I was, and am still, fairly fearful of. If I can even help get you or anyone else over the fear, I’m good.

But I never really believed I could do what I’ve done. I just put one experiment in front of the other and built on it. Then the past year held more travel than the entire 40 years before that.

And I did that while making sure my life cost less than it did while I was sitting in one spot in the US.

To be transparent, all of the above was much less than $50/day. Add insurance costs and things that aren’t day-to-day, and my entire year was around $25,000. That’s so much depth of experience for what is counter-intuitive with regards to cost. We seem so programmed to believe that travel—or a life of nomadic travel—is expensive, but it just doesn’t have to be. Most of my favorite things were just walking the streets of a new area, not spending money, but just watching the people smile and live in their country or city.

Oh. And things kept getting more interesting when 3 months after this I was diagnosed with Type 1 diabetes. Read more about that here.

Hope you’re well. Cheers!

Travel Planning Tips

Figure out where you are going & how are you getting there…
I suggest using at least 2 to 3 different travel search sites. Start with Skyscanner or Orbitz or Booking …or whatever aggregator site you prefer. Then when you see what airlines to use, check their respective sites for better deals or rewards flights.

Figure out where you’re going to stay…
If you’re interested in hostels, search Hostelworld or Hostelling International. For longer-term or more private digs, look at Airbnb, VRBO, or you can look for hotel rooms in the links from the search engines listed above. 

Get comprehensive travel insurance, or in the least, travel medical insurance if internationally…
Especially with Covid not going anywhere, get covered. Start with an insurance aggregator like Insure My Trip, or with SafetyWing, World Nomads, or another. Then decide what is important to you; trip cancellation, baggage coverage, medical, or all of the above. And get a yearly evacuation plan, since you’ll have to get home after your emergency! 

Need more resources? Click here!

The beginner traveler's guide to going nomad book by Jason A. Robinson

Tough Love, Tips & Strategies To Help You Finally Kick-Start Your Travel Life…Or Go Full Nomad!

Been wondering how the hell all those digital nomads, location-independent travelers, and remote workers, travel “full-time?” Maybe you’ve thought about living that life one day, but you’re really not sure where to start.

Beyond giving you the stepping stones to dive into short-term domestic and international travel, this book will show you how long-term travelers extend those tools, maximize their budgets, and turn weeks into months…or even years…of traveling the world indefinitely.

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