I’ve Been a Digital Nomad for 20 Years: Here’s How I Pulled It Off

I didn’t start out traveling intending to be a digital nomad. In fact, the term had only first been coined a couple of years before…

I didn’t start out traveling intending to be a digital nomad. In fact, the term had only first been coined a couple of years before I left my life in Chicago behind, moved aboard my boat, and took off to sail around the world.

Chicago had been fun and had treated us well financially. I worked for myself as a trader on the Chicago Board of Trade—an exciting, high-risk, high-reward living. My wife and I were content and happy until rather suddenly, we weren’t. We were still happy with each other, but we started to question our contentment with our life.

Were we content because we had achieved our dreams, or because we had achieved the American Dream? The two are not one and the same.

With friends fleeing the city to raise kids in the suburbs we began thinking there must be more. We could have kids right now, and join our friends on the next step of the American Dream—it’s certainly what would have been expected of us at twenty-eight—but what stories would we tell those kids? What example would we set? We had never traveled. Never had an adventure. Frankly, if I, at forty-eight, went back and met twenty-eight year-old me at a dinner party, I’d surely think, “This guy is boring.

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How We Decided to Start Traveling Full-Time

One Saturday night, at our local watering hole, we decided to do something about it. What’s the biggest adventure there is, we thought? Little did we know that our answer that night would guide the rest of our lives.

Within months we had sold everything we owned and left Chicago in the rearview. We moved aboard our new 35’ catamaran in Florida and left for the Bahamas days later. We were heading off to sail around the world. We had never been on a sailboat before, but figured it couldn’t be that difficult, and we were right, for the most part it wasn’t. We didn’t run into rocks, we avoided other ships, we watched the weather and didn’t get caught in major storms, we had a pretty nice sail.

Twenty-Year Digital Nomad Veteran boating

Such a good sail, in fact, that two years later we found ourselves in Italy. How much better can life get? Our plan up to this point had always been to sail around the world, return to Chicago with a treasure chest full of amazing adventures behind us, and return to our old lives. We would buy a new condo, fill it with furniture, and whistle on our walk to work each day. While in Italy we looked at each other one day and said, “We can’t ever go back to our old lives. There’s too much to see and do.”

Twenty-Year Digital Nomad Veteran on a boat

After four years, we sailed back into Florida as circumnavigators, and immediately set off on new land adventures. We hadn’t worked during our sailing days because the thought had been to refill the coffers after we were done, but now that the new plan was to never really be done, we had to get going again.

Next Came the VW BUs

Our next big adventure was to drive a 1958 VW bus from Alaska to Argentina, then all over Europe. We lived in that little bus for the next two years, having countless adventures, and seeing some of the most magnificent sites the world holds. We also began working again. The first thing we did was write a book about our sail around the world.

From the start of our trip we had blogged about our adventures, so we had built up a sizable following and had a ready market for a book. That sold very well, staying at number one on the Amazon Adventure category for many months. But perhaps more importantly, financially, I began trading again.

The Twenty-Year Digital Nomad Veteran with VW bus

While we had been off seeing the world, my working world had changed dramatically. Guys no longer went into a building and screamed trades at each other all day long, instead they sat in offices and pushed buttons on a keyboard in silence. Trading had gone all electronic. It wasn’t nearly as much fun, but it created the opportunity I needed to become a digital nomad.

I didn’t trade very much, or very often in those early days. We were living in a VW bus and our needs were small. I would trade when I saw opportunities, make a bit of money, then drift off down the road for a while. Expenses were low, adventures were high.

VW bus

As VW buses have done throughout time, this one produced a baby. With a family now in the works I picked up the pace of trading just a bit. We sold the VW, bought a boat, and sailed down to Mexico.

Our Years Sailing in Mexico

It was actually on the trip south that I first blogged about my trading. The boat had broken a transmission coupling and I had gotten stranded in Cabo for a couple of days. One morning while waiting for a part to be fabricated I made an options trade on IMAX stock that within an hour had paid for not just the repair, but a couple of months worth of expenses. Offhandedly I mentioned the trade, which brought a flurry of e-mailed questions.

a child swimming

This was 2011, and was probably the first time that I truly realized how many people were looking for ways to become digital nomads. Up until this point I hadn’t given it much thought, I just assumed we were one of the lucky few who had realized this path to happiness, and were willing to take the chances that come with the life of a wanderer. ]

Now I saw that there was a large group out there that wanted this lifestyle, but had no idea how to go about achieving it. I decided I couldn’t give anyone a magic pill, but I could at least share my knowledge to try and help them get where they wanted to be. Along with a friend I wrote Live on the Margin, a book about not only the lifestyle, but how I traded stocks to fund it.

When writing a book you do what you can to cover everything, and by the time you hit the publish button, you are sure you have done it. Then the emails start coming in and you realize that you’ve only scratched the surface of all there is to say and to teach.

The Twenty-Year Digital Nomad Veteran with family

I sailed with my now family of four all over Mexico, up and down Baja and the Pacific Coast. It was the most glorious way to raise small children. They were up and walking early, swimming by two, and spitting out their first words in two languages.

My life as a trader continued, but never interfered with experiencing my kids’ growing up. I’d trade a little when we were in port somewhere, then disappear off the grid for weeks at a time. I didn’t own a phone, or an iPad—all my trading was done on a laptop when we could pick up a stray wifi signal from a marina or restaurant onshore.

Yet Another Adventure in an old Dodge RV

Our next adventure was land-based again. I restored a 1966 Dodge Travco motorhome and we set off to show the kids a bit of the US, with nice long drives around Mexico mixed in for good measure. It was during these years that my trading finally became a business.

Again, underestimating just how many people were searching for more than the American Dream, I offered to teach a few of my blog followers how to trade stock options. We would gather in a chatroom, watch the markets, and talk about trading. When I made a trade we would discuss it live. I thought a handful of people might find that interesting. Dozens signed up.

kids playing near VW bus

We traveled mainly in the Pacific Time Zone. This allowed me to wake up early, work, trade, and be done for the day only shortly after everyone else was just waking up. By the time breakfast was cleared from the table I was ready to hit the beach and the waves with the kids. This is what being a digital nomad is really all about, the freedom to do what you want, when you want. To have the ability to earn a living, but not give up your life and your family time in order to do so.

The Twenty-Year Digital Nomad Veteran with kids

For the past few years we’ve been back to boat life, traveling all around the Caribbean. My business, Wanderer Financial, has grown exponentially, as have my children. In order to maintain the right work-life balance I’ve taken on a partner, and together we are able to both cover the stock market, and live life to its fullest.

Trading from anywhere has only gotten easier as cell signals blanket the earth. Remote beaches rarely present a challenge to the digital nomad any longer. After nearly twenty years as a wanderer I can’t imagine working, or living, any other way.


Pat Schulte is a twenty-year digital nomad veteran, having sailed around the world and driven a good chunk of it. His entire adult working life has been as a stock and commodities trader, first in the trading pits of Chicago, and then from anywhere on the globe with a computer. He can be found at his long-running travel blog www.bumfuzzle.com and at his work, www.wandererfinancial.com. Those who would like to join his community of trading digital nomads can use coupon code: WaywardHome to get started with 10% off.

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