How I Stumbled into Digital Nomadism and Backpacked Around the World

In the past two and a half years I’ve backpacked through North and South America, Europe, Africa, and Asia, visited 25+ countries (I have a pending Global Entry application and I’m really hoping that I remembered to list all of them), sailed between two continents, lost (and regained) the ability to walk in Colombia, lost (and regained) the sight in my left eye in Paris, and gotten a rental car stuck (and unstuck) in the sands of the Sahara. Next up is a one way ticket to Norway with a Scandinavian rail pass and a quest to see the northern lights (I got skunked when I tried last year in Iceland). All while being self employed online and earning six figures. My parents still can’t wrap their heads around it and always ask me how I afford to do it. I think they think I work for the CIA.

If you had asked me three years ago about any of that, I would have stared back at you blankly. None of it was even a blip on my radar. I didn’t know what digital nomadism was and had never met a backpacker. But that all changed pretty quickly when I got fed up practicing law and a friend called me out of the blue and asked me if I wanted to go to Japan.

Some background

My undergraduate degree is in mathematics. At the same time that I was in undergrad and grad school (which was in public policy) I was coaching high school athletics (water polo and swimming). That lead naturally to a lot of tutoring of the athletes during my first quarter of college and first season of coaching. I had a knack for it, so word spread quickly. I never did any advertising; my motto was always “do a good job and moms talk.” And boy did they ever. By the end of that first year I was tutoring a ton. It ended up being how I paid for undergrad and grad school without having to take out student loans. All in all, it was a good gig for someone in their late teens and early twenties.

After grad school, I decided to go to law school and moved across the country from California to DC. That naturally put an end to my tutoring, but I didn’t think much of it because I hadn’t really planned on tutoring to begin with — I had just stumbled into it. And I certainly hadn’t planned on doing it beyond my early twenties.

After law school I returned to my hometown in California to practice law at a firm with about a dozen attorneys. I did well there and they treated me well. I even started coaching a bit again when the school I had coached at called me up and asked if I could help out. The firm was supportive of that.

But after a few years at the firm, I decided to hang my own shingle and open my own legal practice. I did alright from a business and financial standpoint — largely because of the connections with the community I had made from coaching and tutoring over the years. But I very quickly realized I had made a huge mistake.

Within a month I realized that I couldn’t stand clients. At the firm I had worked at before I had had virtually no client contact. Now that I was on my own, I had client contact each and every day and it was driving me crazy. The straw that broke the lawyer’s back came the day after I got a resolution to a client’s dispute with their neighbor that my client had been thrilled about. The very next day they emailed me and said that they wanted to file a restraining order against the neighbor for telling them “good morning!” when they walked to their car in the morning. Bangs head against desk. That’s when I knew for sure that if I didn’t find something else to do I was going to end up a cynical, jaded, unhappy lawyer.

A course correction

So I decided to close down the practice. Because I was also a responsible adult, but had been ruined by self employment and could never work for a boss again, I threw up a website that was essentially a glorified resume stating the various things I could do and was interested in. One of those things, naturally, was tutoring. I thought that that might bring in a little money to pay the bills while I figured out what was next. Boy was I wrong.

The tutoring inquiries started pouring in from day one. I thought that I had had a lot of tutoring business when I was younger and coaching, but this dwarfed that. I don’t know if it was the passage of time or the law degree or what, but requests and opportunities started piling up. The SAT, ACT, LSAT, GRE, math, physics, statistics, college applications. Within two and a half weeks I was making more money than I ever had practicing law.

Here’s the other thing that was different with tutoring this time around. I met with most of my students online. I didn’t think much of it at the time, but that turned out to be a big deal.

The call

Within that first year of tutoring I got a call from a friend out of the blue. He was actually a guy I had coached one of my first years of coaching. Since I had been so young, my athletes the first couple years were only a couple years younger than me and many became close friends over the years.

Hey Matt, you want to go to Japan?

With that simple question, the trajectory of my life changed.

Uhhh… sure. When are you thinking?

Later this spring. I was thinking of going for three weeks.

Okay. Yeah, let’s do it! Now that I think of it, maybe I’ll just buy a one way ticket since I’m mostly work online. We can do Japan together and then I’ll continue on to Southeast Asia.

And that’s exactly what I did.

Stumbling along

I’m constantly amazed at how many of the awesome things in my life were completely unplanned. I stumbled into them. Tutoring the first time around. Tutoring the second time around. My first trip as a digital nomad.

And digital nomadism has been one long stumbling experience. When I started, I had no idea what to pack. (Now I travel with just a weekender bag for months at a time.) I had no idea how to find internet or what the deal was with SIM cards. I didn’t know what a hostel was or how to navigate local transportation networks. I certainly didn’t know how many people in the world speak English or how helpful and kind the vast majority of them would be. I didn’t know how to find a doctor in Colombia or Paris (or that the medical bill in the former would be $75 for two weeks of treatment and that the latter would be completely free) or how to get a car out of the sand in the Sahara. But in all those situations and countless others that I had never experienced before, I managed to stumble through them alright.

I think the world has a way of providing for those who allow themselves the opportunity to stumble along instead of constantly planning. At least the last few years have seemed that way to me.