How I Became a Digital Nomad (The 3 Key Steps)
Two weeks after I graduated college in 2022, my lease in New York City ended. The rent went up, and I was out.
I took my laptop, three t-shirts, two pairs of shorts, and a few other essentials to Barcelona, where I’d stay with friends for the summer.
After 90 days in Europe, I continued to travel. Over the next two years, I traveled around the Americas and Europe, working from my laptop. I had extended stints in Barcelona, Medellín, El Salvador, and even the U.S., with dozens of more short visits to different places.
In this article, I’ll share my journey to becoming and living as a digital nomad. If you’d like to live the virtual-work-from-anywhere dream, I hope what I share can help you.
It Takes a Lot of Privilege
The more I have traveled, the more I’ve come to see what a gift it is. So many aspects of my story begin with a head start. My parents paid for my college, so I didn’t have student loans. I was still on their healthcare plan too, so I didn’t have to worry about finding a job with benefits.
Debt-free and insured, all I had to do was make enough money to fund my inexpensive travels. (I spent the first few months on friends’ couches or guest rooms.) I could give freelancing writing a shot without financial stress.
Yet, the other gift my upbringing gave me was the encouragement to explore my own path. My parents never pressured me to go to college right after high school or to study something respectable like finance or law. They encouraged me to figure out what I wanted. Before college, I took two gap years, discovered a love of traveling, and realized I could forge a unique path.
As I look back on the journey, this form of privilege was just as important, as it made it easy for me to realize that I could travel for months on end.
But even with these blessings of being born in the right place to the right parents, here are the steps that I took to make my digital nomad dreams a reality.
Step 1: I Only Considered Virtual and Flexible Job Options
I graduated two years after the start of the pandemic, a time when virtual work had become popular and commonplace, and well before more businesses started asking employees to return to the office. I had the additional luck of good timing.
While in college, I decided I didn’t want to work an in-person job when I graduated. It was off the table. I knew I wanted to travel and have as much flexibility and freedom as I could. I didn’t want to be tied down to a city, saddled with an expensive rent if I didn’t want it.
Years before I’d get on that plane to Barcelona, I was building a way to make virtual work possible.
I Started Freelancing Writing a year Before My Travels
I started freelancing writing while still in college. I was running out of personal savings from my gap year. I could have gotten an on-campus job or something else, but I was thinking ahead. What could I start building now part-time that I could launch into full-time when I graduated?
I started freelance writing, even if the pay was meager at first. My first gigs were writing blog posts for $75-$100. This was before AI. I spent 5-6 hours on those first articles, making sure they were as good as I could write them. I was thinking about long-term opportunities.
Throughout college, I gathered a handful of clients who were now paying me $200-$300 per article. Through a few friends, I even got one big client with (at the time) a large monthly retainer.
By the time I graduated, I was making a modest, but relatively comfortable income I could live off of, as long as I didn’t intend to live in New York or some other ultra-expensive city.
So if you want to live the digital nomad life, start scheming on what virtual job you will have today.
Build Connections Now
I succeeded as a freelancer for two core reasons. I could write. But that wasn’t enough. I had friends at marketing agencies and others who ran e-commerce brands. (Thank you, especially to my friend Peter Tzemis, who handed me freelance jobs for his various companies as if they grew on trees.) I leveraged previous connections from my time in the fitness industry. I posted on social media about copywriting and blog writing, focusing on the health and fitness industry.
This post from February 2022 with 60 likes landed me a long-term client who, within six months, was paying me over 1k a month. (I left for Barcelona in June 2022.)
Eventually I had 4-5 steady clients. I never used Upwork, Fiverr, or LinkedIn.
I was lucky too, that ChatGPT 3.5, the model which would change freelance writing, had not yet been released. By the time it did, I had shifted partly away from freelancing and had a part-time copywriting job, where new technologies only helped me improve.
“Wow David, sounds like you just got lucky over and over.” I sure did. However, opportunities still exist, but they look different. Another business lesson I learned from my friend Peter is that timing is everything. Just because my exact path wouldn’t work today, doesn’t mean there aren’t other opportunities where you’ll look back and think “Wow, the timing on that was great, how’d I get so lucky?”
If the timing wasn’t right for that form of freelance writing, I’m confident I would’ve gone down a different path in search of virtual work.
Yes, This Means I Made Less Money
I didn’t apply for fancy marketing or advertising jobs on Madison Avenue. I didn’t consider pivoting to something that would crush my soul. Yes, I likely turned down a high salary that my NYU degree would’ve helped me land, but that was never what I wanted. I wanted to travel. I wanted to live. I wanted to explore what this world had to offer me. That meant saying no to money.
(I probably saved more than I would have in the long term because I spent the next two years in places that cost a fraction of what it costs to live in New York.)
What Flexible Job Would You Want?
On the digital nomad subreddit, one of the most common questions people ask is what job people have that allows them to travel the world while working.
I can only speak to my experience, but there are a few things I’ll mention:
1. Working as a Contractor is Easier Than an Employee
As an employee, working abroad is legally gray, and your job likely won’t want you to. Even if you’re virtual, many big businesses have a problem. As a contractor, you technically work for yourself.
At my part-time job, I started as a contractor and for months was in a different time zone without issues. This made the transition to employee much easier. Also, it’s a small business where getting the work done matters, not bureaucracy. So if you want to be an employee, smaller businesses will likely have more flexibility.
2. Most internet jobs
On the STEM side, software engineers and cybersecurity come up a lot.
If I were starting from scratch again, I’d look at learning something like e-commerce. Just because freelancing isn’t what it used to be, brands who sell stuff are still looking for marketing minds. You just need to be more interdisciplinary now, and not just a “copywriter” or “graphic designer.” You have to understand brand, sales, or creative on a high level and know how they connect.
3. If You Think You’ll Be an Influencer…
Everyone wants to be an influencer or full-time creator, which is a fine side hustle, but I don’t view that as a viable career path unless you already have something getting off the ground. Most full-time creators take several years of consistent content creation to get there.
Step 2: Free Yourself of Society’s Shackles (And Your Own!)
About 50% of conversations where I talk about my life, someone says, “Wow, I wish I could do that.” It’s rarely the parents of young kids, or those working two jobs, or those caring for elderly parents who say this.
It’s often those who, on paper, have as much freedom and privilege as I do.
My friend Reis says that our society lacks, “Mental Freedom.” I love this framework. Many of us have the freedom and opportunity to travel as much as we want, but we choose not to take it. We are like the tiger who goes to the zoo and gets used to living in the cage. Once released back into the wild, the tiger continues to pace the distance of the cage.
Examine The Fears That Are Holding You Back
This idea is one of the reasons Tim Ferriss’s The 4-Hour Workweek has become the perennial seller it is: it pushes back on our assumptions about what work and retirement have to look like. (It also tops my list for book recs for digital nomads, which you can read here.)
This step was easy for me because it was a skill I had already developed in my gap years after high school. If you want to be a digital nomad, you can’t be afraid of taking the unconventional path.
Accept Any FOMO Coming Your Way
I was sad that I left my apartment on the Lower East Side and an adventurous bachelor life. Immediately when I left, I missed the punk scene, my bodega and its chopped cheese sandwiches, the coffee shop I worked out, and the diner nights with my friends from college.
Yet, I had different experiences. I learned languages, traveled the world, made more friends, and learned so much.
There are two sides to this: First, a “yes” in life means a “no” for something else. That’s not the end of the story, because no decision was permanent. I could always look for “real jobs” in New York if I really missed chopped cheese sandwiches.
To have many great options for roads to take in life is something I’m incredibly blessed to have. If you’re struggling to decide over two great fates, pause to recognize how lucky you are.
This framework helped me accept and embrace my choices.
Step 3: Finding Balance and Building Routines
The digital nomad Reddit threads are filled with countless stories with headlines like “not for me.” It’s true — traveling and working on your laptop is not for everyone.
Within these stories, I see the tale of somebody who approached the digital nomad life very differently than me.
Take Care of Your Routines
This is not a weeklong vacation. This is your new life (for now.) That means you should sleep well, exercise, and choose nutritious meals at least 80% of the time.
It means you need to figure out what work schedule works best for you.
In Europe, I was more productive than ever because clients couldn’t bother me in the morning because of the time difference. My routine in Barcelona had a rhythm I came to love. I walked to the coffee shop and sipped on a cafe con leche and a sandwich. Then I went to the co-working coffee shop and locked in from 9am-2pm. I’d eat lunch, nap (remember this is Spain), work from 4-6, and go to the gym. I did this four days a week. On other days, I’d often just work in the morning.
On lighter work days, I only worked in the morning. I always joined gyms wherever I went, and I found a few reliably healthy, inexpensive places to eat.
Having normal life routines was critical for me to sustain this for months.
I found this to be a more authentic way to see places anyway. I saw fewer tourist attractions and spent more time in the spaces that locals spend time in. I took advantage of weekends and the occasional slow afternoon to explore. Since I could stay as long as I wanted, I never rushed to see everything I could.
Many digital nomads talk about how lonely it is. I didn’t have that experience at all. I made a point to meet locals wherever I went. Many of my best friends live in Barcelona. Even when I went to Italy by myself, I timed the trip to be able to see two punk shows. I had a great time moshing with my fellow punkers in Bologna.
Of course, it depends on your personality, but I think one of the beautiful things about spending lots of time in different countries is learning about their culture, how they live, and embracing that.
Don’t Spend Too Much Time In Hostels
I stayed in my fair share of hostels. Bunk beds with 20 somethings is fun for exactly four days. On day five, I’m out. Get an Airbnb, even if it’s a bedroom in somebody’s home. (In fact, I prefer staying with somebody, because then I can get a more local experience and local recommendations.)
If You’re Able to Read This Article, You’re Probably Able to Make it Happen
Start plotting career moves. Make connections. Prioritize flexible options. Let go of societal expectations about a “normal” life or career (those don’t really exist anymore anyway.) Last, treat the nomad life just like you’re life. It is your life.
Why I’m No Longer a Digital Nomad
This lifestyle never dragged on. I could have kept going. Yet, I was also ready for the next chapter in life. After two years, I decided to get a lease. I write about this decision in this article on the pros of cons of the digital nomad life.
Where to Go!
Check out a few of my digital nomad destination guides.
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