Lessons Learned from Island Living


Just a few years ago my wife and I sold most of what we owned and moved to a Caribbean island. It was an adventure into the unknown for sure, but very exciting. I look back at that time fondly and feel it was a very formative to how I want to live my life going forward.

The stars aligned and we felt it was time to take action on something we had talked about for a while. We sold our house, and a lot of our furniture and possessions, packed up everything we thought we needed and could take with us on a commercial airplane and headed off. Our suitcases, dog and cat, and a sense of unease accompanied us as we got off of the tiny 8-seater plane on the Caribbean island of St Croix. St Croix is a tiny island that’s part of the US Virgin Island chain just east of the island of Puerto Rico. It’s a United States territory which made traveling there incredibly easy, it was just like traveling to any other state in the US (with some minor US Customs acceptions). The 28 mile long island is known for it’s beautifully clear blue oceans, scuba diving, rum exports, and a laid back atmosphere.

For us the move meant a new adventure, a change from our career focused, non stop going and doing lifestyle to something new. It wasn’t a way to start over or start fresh, but rather a way to enjoy what we had already accomplished.

Many of our closest friends on the island were retired, they’ve lead successful lives building businesses and raising families. They now had the opportunity to slow down and enjoy the warm Caribbean breezes and afternoon rum drinks. I admire a lot of what they had accomplished and have used that to continue to guide my own journey and goals.

These lessons aren’t totally concepts new to me, but the experience has had a great impact on how I think about my actions and interactions.

A little kindness goes a long way

Everyone has a story, and most are really, really interesting. Growing up I didn’t see a lot of other cultures or demographics of people. Sure we traveled and experienced a lot of cool things, but I hadn’t immersed myself in other’s ways of thinking or different types of foods. It was often said on the island that you’re either running to something or you’re running away from something. I think for us it was a little bit of both. A bit of fun in the sun and a lot more about self-discovery.

One of my favorite cultural behaviors was when everyone would say “Good Morning”, “Good Afternoon”, “Good Night” (time of day dependent of course) where ever they went. If you walked into the bank lobby and there were 10 people in line, you would say loud enough for everyone to hear “Good Morning”, the entire group would return your “Good Morning” and continue on with their business.

You probably don’t need that thing

On an island, if it can’t be grown or made from materials found solely on that island, something has to be imported onto the island. Pretty much everything has to come in by boat or plane. Everything!! For a long time this fascinated me, how everything that surrounded us was brought onto the island at some point, it may have been repurposed several times. Even the original forts on the island were built using bricks carried in by the ships that first sailed to settle the island.

We learned really quickly that our habit of running out to the store to get exactly what you wanted, whether you needed it or not, or ordering something online and it arriving on your doorstep a few days later, just wasn’t a possibility. Because everything came by boat or plane the prices were a bit higher than we were used to in the United States. Some items, especially frozen foods were 2-3x more expensive, luckily we don’t eat a ton of that, but it would’ve been cost prohibitive to even try. We focused more of our time, energy, and money on the things that improved our interactions with others.

We’re all in this together

On an island you are all literal confined the size of the island. Surrounded by water and many miles from the next group of people. Travelers will come and go, but survival and prosperity depends on working and living together as one island. There is a lot we can do and probably more that we try to do on our own. I’ve found that giving to others and allowing yourself to take what’s offered from others can be far more important.

No one really cares what you have or own

Status symbols loose a lot of their luster when exposed to the harsh salt water air of a Caribbean island. When we arrived, suitcases in hand, we needed a way to move around the island. We rented cars, borrowed cars, bought a lemon of a car, but eventually bought our island car. That car was a 4-door Ford Explorer, it was a manual transmission and probably 13 years old when we bought it. It was the definition of an “island car”. It was white, with large sections of peeled paint. 3 of the 4 doors opened, 3 different doors locked. The hood and back hatch no longer stayed up on their own and required some creativity to keep them open. And I loved that car. We paid $3,000 USD cash and it did a great job for us.

In many other places or with other groups of people we might have felt judged for type or condition of the car we drove or the cloths we wore. On the island it didn’t matter what we could “show” we had, what mattered was the person we were. I’ve never been much for name brand things, but this really cemented the idea that it didn’t really matter the objects I had. That only impresses someone for a short while, the authentic person you are is what actually matters.

For me I was living on an island with zero debt, money in the bank, my beautiful wife beside me, and a smile on my face. That was the accomplishment. That brought us peace.

Enjoy where you are and who you’re with

Island time is a measure of time that can be a few minutes, hours, or days. The slower pace forces you to slow down and soak in the people and the experiences that surround you. I had been in the habit of always moving and doing something. While I was doing one thing I was also preparing to move onto the next thing, never really focusing or enjoying the time and space I was in.

Enjoying the sights, smells, laughs and adventures became the mission for me. I would often think what I could see and do and share with others.