The Full Story of How I Stumbled Into The Digital Nomad Life

Everyone has a dream about what their future would look like if there was nothing holding them back.

If you didn’t have a job to wake up for every morning. If you didn’t have a mortgage to pay. If you had money in the bank and the time to travel wherever your heart desired, whenever you wanted.

I had that dream too. All through high school, then college, then grad school, I had an idea of what my perfect reality looked like. Maybe I’d buy an old Airstream and visit every National Park. I’d spend my winters somewhere that didn’t have snow. I’d visit new cities every month, exploring the country piece by piece.

But at the time, it was never more than a dream. After all, I was on “the path.” I was getting the education I needed to pursue a career that would pay the bills and allow me to buy a house and a car and a week-long vacation every year. I figured that my dreams of traveling whenever I wanted would have to wait until I retired at 50, 60, or older. I never even knew that the digital nomad life existed.

I saw my impending graduation date as a deadline.


I had enjoyed my summers off and a few week-long holidays throughout the year that come with an American school year. I’d spent them traveling with my fiancee and my parents, or on my own. But after graduation, I knew I’d be lucky to get more than a week or two of vacation time for the next few years.

So I started packing as much travel as I could into my remaining year of school holidays. Since I was living on a stipend from my graduate assistantship, I started scouring local ads for part-time jobs. But I was attending grad school way out in Missouri, and I didn’t want to be tied to a job that wouldn’t allow me to go back to Ohio during breaks. So I started scouring the internet for side hustles. That was when I discovered freelance writing for the very first time.

I already knew that I had the writing skills, so I started reading everything I could find about landing a freelance job. I started a profile on Upwork and landed my first gig a few days later. It paid an incredibly small amount for several hours worth of work, but I didn’t care. I had made something out of nothing, and I was on my way to earning the money I needed to take a trip over winter break.

The more I explored the world of online content creation, the more hooked I was. And the more money I made.

Pretty soon, I was writing around the clock. I made enough to take a trip to the Florida Keys. In fact, I made enough to pay for flights for me, my fiancee, and my dad.


Then I made enough to start paying for another trip. This time I booked my mom and I flights to our favorite spot, New Orleans.


With graduation fast approaching, I pushed off applying for jobs because I was so hooked on landing that next paycheck from my writing. Pretty soon graduation was a month away, and I realized I didn’t know what in the world I was going to do.

It took a long time for the idea to hit me that I could pursue my freelance career full-time. When it did, everything seemed to click into place. If I could turn this into a full-time career, I could avoid the 9-to-5 I was so dreading. I could travel whenever I wanted to. I could follow my fiancee wherever he landed a job. I decided to go for it. At the time, I told myself that it would just be short-term. Once the fiancee landed a job and we got married, I’d find a full-time job that paid better.

Now, almost a full year after graduation, I’ve managed to exceed the income I would have been making at a full-time gig in my field.

I’m traveling to new places every month, chasing deals on flights and hotels. I’m able to spend part of my time in Ohio with my folks, and part in Nashville with my fiancee.


At this time, I have no plans of applying for an office job in the future. Besides the ability to travel and create my own schedule, I’ve also grown to love that freelancing gives me the ability to constantly work to increase my income. If I want to save for a trip or another big purchase, I can work extra hours and make extra income. As I add more skills to my repertoire, I can increase my rates, and make more money for less work. It’s an addicting feeling.

The digital nomad life isn’t without its challenges.

It can be tough to get motivated sometimes. I don’t get benefits like sick time or insurance. If I don’t work or can’t work, I don’t get paid. During holidays, work will occasionally lag, and my income takes a dip. 

But for me, the benefits far outweigh the challenges.

Are you dreaming of starting a digital nomad life, too? Join my mailing list below today to subscribe to my newsletter to get the latest tips and tricks to help you build your own successful freelance career.

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