My First Year as a Digital Nomad: The Reality Behind the Photos

Ben Maguire
Jan 19, 2020 · 10 min read
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By now, there’s a good chance you’ve heard of the “digital nomad” lifestyle. And if you’re familiar with it, you’ve probably fantasized about it at one point or another. Traveling the world, living in postcard destinations, working remotely from a laptop when and where you please — it’s the ultimate dream, right? It is for me anyway, and it has been ever since I first learned it was possible.

My Path to Becoming a Digital Nomad

In 2015, I was living a very “normal” life. I was 24 and I had somehow landed a job at a digital marketing agency despite bringing nothing more than a B.A in philosophy to the interview table. It was a great first job out of college. The atmosphere was ultra-lax and I had a friendly relationship with my boss and coworkers. Half my department was out playing ultimate frisbee, volleyball, or basketball at lunch on any given Friday (sometimes Thursday). Ping pong started at 5 p.m. sharp. I definitely couldn’t complain.

There was only one problem: after a year, I was beyond bored. Some people thrive on routine and stability, but others (like myself) abhor it. I was doing the exact same thing, week in, week out — a ‘Groundhog Day’ scenario of sorts. But I accepted it. That’s just the way things are. You have to hold down a respectable job to pay the bills.

And, relatively speaking, I had it pretty damn good. I wasn’t earning much, but I also wasn’t stressed (like so many others in the corporate world). Life was easy — but I was jolted out of my complacency when I went on my first paid vacation to Costa Rica.

I’d done a fair amount of traveling in Europe, but something about Latin America was different. The tropical beauty, the relaxed vibes, the simplicity of life…it was infectious. I couldn’t get it off my mind. As soon as I returned, I began scouring the internet for travel inspiration, already planning out my next PTO trip.

That’s when I came across travel bloggers like Nomadic Matt, Expert Vagabond, and Alice in Wanderland. They’d all been traveling the world non-stop for years, financially supported by their blogs. What!? That type of life exists!? I was obsessed. Surely that was the highest form of human fulfillment, I thought — and I craved it.

Fail, Fail, Then Fail Some More

Fast-forward to 2017. I had miserably failed to launch my own travel blog (it’s especially hard to do from a corporate cubicle). Instead, I spent an entire year stashing every spare penny into a separate bank account I named the “Freedom Fund.” With a pretty sizeable sum, I quit my job and bought a one-way ticket to South America.

It was arguably the best nine months of my life, full of new experiences, unforgettable moments, and an overwhelming appreciation for the world around me. It just felt right — as if I had finally found my true purpose. During that time, I brainstormed two business ideas which I hoped would enable me to continue traveling indefinitely.

When my Freedom Fund ran out, I returned home and gave my first business idea a try. It was a t-shirt dropshipping website, and it failed quickly. My second idea was a sustainable clothing brand. It failed, less quickly, but more painfully. At that point, I knew it was time to get a “real” job again — that or continue living with my parents at age 27.

So, I went through the motions and was fortunate to land another job at a marketing agency in downtown San Francisco. But I hadn’t forgotten about my digital nomad ambitions.

In my spare time, I was still testing out ways to make an income online. First, I spent an embarrassing amount of money for a course on starting your own social media marketing agency. Failed. Then, I started running lead generation campaigns for a Realtor using Google Ads. That time I actually got a little closer, but ultimately failed again.

Going All-In on Freelance Writing

The scoreboard was disheartening: I’d racked up five failed attempts to earn money online. I don’t want to discredit any of those methods — they just weren’t the right fit for me. Admittedly, I underestimated the amount of time, effort, and investment each approach required, always moving on to the next shiny idea when the going got tough. But as the stress and dissatisfaction at my new corporate job grew, my mind was clawing for a way out.

Then, one Monday morning, I snapped. I was sitting at my desk, dreary from a weekend of drinking, listening to the click-clack of keyboards echo throughout the otherwise silent room. In that moment, I was suddenly struck with the feeling that I could blink and 15 years would pass by. I’d still be right there at the same (metaphorical) desk. Sure, I might have a different title with a higher salary — but nothing would truly change. I needed to escape that fate.

I went all-in. I put in my two-week notice, broke my lease, and picked out a small, charming town in Mexico with hostels starting at $5 per night. I bought another one-way ticket, but this time I didn’t have a large Freedom Fund saved up. I urgently needed to crack the online income code. There was no turning back. I was in too deep.

My plan was to pursue a career as a freelance writer. Rather than jumping at what my newsfeed’s ads were preaching (dropshipping, social media consulting, etc.), I asked myself, “What am I already good at?” As a writer, I’m very skeptical of my own talent, but I had always excelled at written assignments in school. So, I created a portfolio of writing samples, then headed off to San Cristobal de las Casas to give the whole digital nomad thing one more shot.

Downsides of a Nomadic Life

My flight to Mexico was on January 4th, 2019. As I write this, it’s now 2020, and I’ve spent most of the past year backpacking through foreign countries. After nearly five months in Mexico, I briefly returned to the States for two weddings, then booked another one-way flight — this time to Bali. From there, I moved upward through Malaysia, Thailand, Cambodia, and Vietnam, writing articles for various clients along the way.

So, technically, I made it! The decision to quit my job in favor of becoming a nomadic freelance writer wasn’t a complete disaster. Rather, it’s been a rewarding adventure and I’m proud of how far I’ve come.

And yes, I’m guilty of only posting the glamorous aspects on social media: the beach sunsets, the smiling selfies…I even used a #nomadlife hashtag in one post. I’ve received messages from far-off acquaintances asking me what I do for work and how I manage this liberating lifestyle. But the pretty pictures are only one side of the story. Along the way, I’ve experienced stress, doubt, loneliness, and other issues that I don’t share very often.

I wrote this article to paint a more complete picture of what one year as a digital nomad has been like. It’s been incredible, and I don’t regret my decision at all. But, in light of how many people are captivated by the digital nomad lifestyle, I feel it’s necessary to tell the whole story — thorns included. While the following points are based on my personal situation, I’m sure there are plenty of other nomads who can relate.

I’ll just get this out of the way up-front: I didn’t make very much money in 2019. In my first month as a freelance writer, I made $275 — and it actually went downhill from there. In my third month, I made $185 and I was seriously doubting my decision. But, due to the circumstances, I had no choice but to push onward. And I think that’s a large part of the reason my freelance career eventually turned around.

My dedication to previous side-hustle attempts was very short-lived. If things were looking bleak at the three-month mark, I’d abandon the project for a new venture (and we saw how that turned out). But in Mexico, after leaving everything behind, I didn’t have that option. I had to keep going.

After the third month, my freelance career started to gain momentum. I was on track to have my first $1000 month and I began securing higher-quality clients. My trajectory was far from stable, but my digital nomad future was beginning to look brighter.

That being said, looking back on 2019, even my best financial months with freelance writing wouldn’t have been enough to sustain a comfortable life in California. But I don’t need that much. With my minimalist tendencies (traveling in cheap countries, staying in hostel dorms, rarely buying material goods), I can get by on far less than even the most modest budget back home.

Nevertheless, here’s how unstable my freelance income was in 2019:

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I was definitely stressed about money during those low points. Now, it should be noted that part of the instability is my own fault. For one, I’m a slow writer, which puts a handicap on the amount of work I can crank out and the number of new clients I can take on. I also wasn’t putting in full-time hours, but that would contradict the whole point of being a free-spirited nomad, no?

I digress.

The bottom line is that freelance work is a never-ending hustle. When I arrived in Bali, I lost my main client within the first month and had to start over from scratch. I’m an independent contractor, which means there’s no guarantee a client will continue working with me long-term. That’s why, for freelancers, the feast-and-famine cycle is very common — and riding that roller coaster can be mentally taxing.

If you browse through my Instagram, you’ll see some pretty cool photos (at least I think so). But many of those photos were taken weeks apart. What happened in between? Honestly, not much. When I have work to do, or when money gets tight, I revert to a pretty bare-bones existence. Take my time in Mexico City for example.

Here’s an excerpt from my journal in CDMX:

“…I don’t feel like I’m traveling or exploring here. My life is actually very similar to how it was in SF: do almost nothing except work and exercise during the week, followed by binge drinking and girl-chasing on the weekend. Now that I think about it, it’s actually a perfect mirror image of my life in SF. Old habits die hard? But this is really starting to nag at me…my lack of notable experiences has me once again in a place of mundanity.”

How’s that for an Instagram caption? Not very inspiring, is it?

Throughout my first year as a digital nomad, I had multiple instances of feeling “stuck” like this. Sometimes it was because I was low on money. Other times it was because I needed to focus on work. And usually, it was a combination of both.

The result can be very isolating. Unlike at home, I didn’t have any close friends or family to turn to, and most of the travelers I met were in completely different boats than me. They would quickly come and go, seeking out fun experiences while I was busy typing away in the hostel lobby. And when this sort of social dissonance persists over a long period, it can begin to feel like you’re living on an island — a one-man band, separated from those around you.

…which leads me to the next drawback:

3. Short-Term Relationships & Loneliness

Bonding on the backpacker circuit is usually quite temporary. Nomadic Matt once referred to travel friendships as “single-serving friends.” You might have a blast with certain people for a few days, but connections rarely last longer than that. Everyone eventually goes their separate ways.

To illustrate this, here’s an excerpt from my journal in Bangkok:

“The highlight so far was meeting Ana from Brazil. We went to a vibrant night market filled with delicious foods. After sampling some skewers and ribs, we sat in a rooftop bar drinking beer to meaningful conversation. But as with all backpacker relationships, it ended as quickly as it started. She left the next day, once again reminding me of the reality on the road: you’re surrounded by wonderful people, but they all have one foot out the door.”

Meeting loads of new people is fun at first, but it can grow tiring after months on end. The same introductory conversations play on a loop, over and over again. After six months, I felt like I had been asked the question, “How long are you traveling for?” a thousand times. I began to long for deeper connections with people who actually knew me, and the isolation I mentioned in the previous section only compounded that feeling.

Because of this, there were times I felt very lonely, even when I was sitting in a room full of friendly, vivacious people. I lacked the enthusiasm to strike up another intro conversation. What was the point? They would be leaving in a few days and I’d be back to square one.

I’m not saying that, as a digital nomad, I feel this way all the time. But it’s certainly occurred more than once. I’ve gained a great deal of appreciation for the importance of human bonding (both romantic and platonic). It’s vital to our happiness, but deep connections are hard to establish when you’re in a state of constant flux.

Final Thoughts: I Still Love the Nomad Life

I feel conflicted as I write this. More recently, I’ve come into a new perspective that recognizes how trivial these “problems” are in the grand scheme of things. I feel spoiled for even suggesting that the past year has had any real downsides, like a rich teenager complaining about the new car they received.

Overall, my first year as a digital nomad has been a blessing — one I am eternally grateful for. But this article was written in the spirit of transparency, so I must acknowledge the negative mindsets I had during my travels.

All things considered, I’d do it again in a heartbeat. The pros far outweighed the cons, and in life, some negativity is necessary to give meaning to positivity. As I look forward to the next year, I hope that I will continue to be able to roam with the same freedom that’s been bestowed upon me since I first set foot in Mexico over one year ago.

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Ben Maguire

Written by

Freelance Writer / Digital Nomad. Hopelessly restless, a night owl fleeing from boredom. IG: bw_maguire

The Startup

Medium's largest active publication, followed by +771K people. Follow to join our community.

Ben Maguire

Written by

Freelance Writer / Digital Nomad. Hopelessly restless, a night owl fleeing from boredom. IG: bw_maguire

The Startup

Medium's largest active publication, followed by +771K people. Follow to join our community.

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