The Digital Nomad Wandering Life

Things I’ve Learned While Sailing and Driving Around the World

In 2003, at the age of twenty-nine, my wife and I went from living and working in downtown Chicago, to pre-retirement and sailing around the world. It was a dramatic shift for two mid-westerners who had never been on a boat before, and also were far too young to be retired in the traditional sense.

Our plan had been to sail around the world, sell the boat, move back to Chicago, and slip back into our old life. We’d be four years older, and have a ton of great stories to sustain us until we were much older, and could retire via the traditional route, after many more years of work.

But while sailing we realized something important, there’s a big world out there, with a lot to see and do, and we weren’t particularly interested in slipping back into the American way of life any longer.


Obviously, that realization does little to answer the question of how we would earn a living in order to sustain a lifestyle of world travel for years, or decades to come, but in the end we figured it out. We took what we were good at (trading/investing), turned that into an ongoing source of online work.

We also branched out into new endeavors, such as writing books and magazine articles. But perhaps more important than just figuring out how to fund this lifestyle, are the lessons we learned to truly enjoy it fully.

Living a truly nomadic life sounds ideal, but it’s not always rainbows and unicorns. Here are a few things that transformed and sustained this lifestyle for our family, making it more fun and interesting over the long term.

----------->  Read the rest of the article at A World To Travel

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Living and traveling on a boat means for a few months each year we have to wait out hurricane season. This year we did that in Aruba, and have had a great time. It's not the greatest cruising destination, but it's outside of the hurricane belt, and it does have world-class diving. It's also a great place to hunker down and get some work done, both around the boat and on the computer. One of the best things about the Wanderer lifestyle is the ability to live and work in some of the world's most beautiful places, and Aruba fits the bill.

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