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

Living the Dream

As the title of this blog hopefully indicates, I am a developer who lives on an island, a tropical island to be precise. North Caicos is a quiet island in the Turks and Caicos Islands (TCI). Roughly a million people spend a fair amount of hard-earned money to vacation here, including the random celebrity or two, and I get to live here half of the year. A number of fellow developers have said to me, “You’re living the dream.” The photo in the header was taken from my back deck, so yes, life is good.

There are two questions that people ask me right away:

  1. What’s it like living there?
  2. How did you manage to make it happen?

The second question has a lot of answers which I’ll talk about in other entries, so let’s get to the fun part first. North Caicos is a relatively small (40 square miles), lightly populated (1500 people) island with an amazing beach, and hardly anyone knows about it. The photo below was taken during the middle of a beautiful day in tourist season. The most people we’ve ever seen on the 1 mile stretch are 20. Yep, 20.

Empty Beach Continue reading