How Do I Get to Live on an Island?

When people find out I live on a tropical island for half the year, the first question they often ask is, “wow, how do I do that?” Short answer, it’s not easy. So, I’ll tell you a story about how we did it, and then I’ll try to give you a better path. Continue reading

So You Want To Live on an Island

As you may have read in Living the Dream, I live half-time in North Caicos, a small island in the Caribbean. When finding this out, fellow developers want to know how I managed to make it happen. I’ll talk about some technical considerations later, but the question is really about how you can position yourself to work in paradise. “You may ask yourself, well, how did I get here?”1 Lots of folks work, as an old co-worker of mine once said, their ordinary job in their ordinary way for their ordinary pay. It is the seemingly safe thing to do, and I fell into that pattern as well. Often, however, people want more, and when presented with proof that it is actually possible, the wheels start turning.

When I was growing up, I wasn’t ambitious. My family didn’t come from money, and most everyone I knew worked their ordinary jobs. I grew up thinking you went to college, and then you worked in a profession until you retired. The idea of starting a company never occurred to me. Why, I’m not sure, because a close friend of the family was an engineer who owned his own company. Yep, I had a mentor right there in front of me, and yet didn’t see it. I was constrained by my ideas of a normal life. Continue reading