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AAA Traveler Worldwise | Travel
Remote Work Reimagined


More than a decade ago, the deal was that my husband would return to his beloved Jamaica during retirement. Since he would hang up his hat sooner than I—he is much older than I am—at some point, I would become a snowbird. I’d leave the New York winters for Jamaicas sunshine, until eventually retiring there full-time, too.


But while you have your plans, life has its own path. A layoff moved up my husbands retirement timetable by several years. We started building a home in 2014 in Jamaica, and when it got to the point where it was livable yet still unfinished (meaning the basics like the walls were up and windows in), he headed for the island’s sunny climes in 2016. It was not a good time for me to start the snowbird trek yet. I wanted to stay close to our adult daughter and had work commitments that tied me to New York. I didn’t need much space, so I rented a room in a house. 

Working remotelyWorking remotely opens up new possibilities for your workspace. Photo by Lucas/

A couple of years passed. I didn’t travel frequently to Jamaica at first. It wasn’t quite ready for me. My husband “roughed it” with sparse internet service and without a fully working kitchen or plumbing system. I was okay waiting. By 2018, as work on the house progressed, I juggled my visits to Jamaica with my travel for work and spent more time there. 


But once again, life did its thing and COVID-19 hit. I stopped traveling. Suddenly, my world was reduced to that small room I was renting. After months of going out only to get groceries, the walls began closing in on me, particularly since I was used to taking a few trips a month for work. Something had to give. I was going to lose my mind. I cant remember when I had the epiphany, but I decided to escape to Jamaica.


With the advent of COVID, my freelance fact-checking job became remote. I could work from Jamaica, giving me a steady income to pair with my freelance writing. Plus, there was no mortgage on the house in Jamaica. For six months, I saved my money to move and kept my sanity by fantasizing about what it would be like in paradise, me on my laptop writing on the beach.

At the end of September 2020, I packed four big plastic barrels, which people typically use for shipping to the Caribbean, and sent them to Jamaica, saying goodbye to the Big Apple. It was bittersweet leaving my daughter, friends, community and the security I had built for myself over the last 30 years. I was going to another country where I knew only my husband. It would be a different world.
The startling beauty of the Blue Lagoon in Port Antonio, Jamaica. Photo by dbvirago/Stock.Adobe.comThe startling beauty of the Blue Lagoon in Port Antonio, Jamaica. Photo by dbvirago/
Our house—with five bedrooms, three-and-a-half baths, and upper and lower decks—is in the rural parish of St. Mary. This locale would be a big change for me. After decades of jumping on the subway and Long Island Railroad with ease, I would need to be driven by my husband pretty much everywhere. I was too timid to drive on the opposite side of the road from what is the custom in the States.

But ever the adventurer, I was up for the challenge. After all, I would live by the sea, able to lie in my bed and see and hear the ocean. I turned one of the bedrooms into an office of sorts; it had an ocean view, and when I desired, I worked at a table we had outside. This was a far cry from being cooped up in that little room in New York where I struggled to breathe. Jamaica was a massive exhale.
That’s not to say that paradise didn’t have imperfections. Living in the US, I took infrastructure for granted. In rural Jamaica, I could make no assumptions about anything, especially electricity. We have solar energy and, thankfully, abundant sunshine; but during the rainy season, I quickly discovered solar’s limitations. For backup, we opened an account with the electric company, but its service sometimes proved unreliable, as did the sole internet service provider. I finally got hip to an alternative for the internet and bought a device that works as a hotspot.
White sand beaches like this one in Negril are among Jamaica’s numerous attractions. Photo by Chee-Onn Leong/Stock.Adobe.comWhite sand beaches like this one in Negril are among Jamaica’s numerous attractions. Photo by Chee-Onn Leong/
That stuff, while nerve-racking, wasn’t a deal breaker. But I missed friends and family and my old way of life. It was at least 30 minutes to a supermarket, and since we don’t have a street address, ordering online wasn’t an option. I was homesick.
Even though I had visited Jamaica numerous times over the years, I quickly discovered that vacationing here is one thing, but living here is another. If you’re considering working remotely, especially in an exotic locale, know what you’re getting into. Investigate the infrastructure, and think through things like access to shopping and other necessities. When you’re in for the long haul, small inconveniences can loom large. There may be Facebook groups and other resources for remote working that can help you make the best decision.
Ackee and saltfishAckee and saltfish is a traditional Jamaican dish made of salt cod and ackee fruit. It’s served here with callaloo and johnny cakes. Photo by paul_brighton/

In the end, I have no regrets. There have been life-changing upsides, like the health benefits of being surrounded by beauty. What the scenery does for the soul surpasses anything I could have imagined. It restored some of what big city life chewed up. Early morning hikes in the jungle near our house. Strolls on the beautiful beaches and dips in the water. Lunch by the river. Splashing in waterfalls. Rafting on the Rio Grande. Feasting my eyes on the bluest of blues of the Blue Lagoon. Indeed, this is the good life.
After a certain point during COVID, it was safe to travel on-island to places like Negril, Bluefields, the South Coast in Whitehouse and the off-the-beaten-path parish of Portland. Everywhere, the landscape is lush with jungles, mountains and fantastic beaches like Frenchman’s Cove, where the water from the Blue Mountains flows to join the Caribbean Sea. The sea and river combination is magical and made more dramatic with the canopy of tropical greenery and white sand beach.
I found much joy in discovering the island’s nooks and crannies. And I’ve never eaten so much fish. Fishermen frequently stop by the house to see if we’re interested in the morning’s catch. I was settling into a groove.
Then my spirit pulled me in another direction. This past spring, I hit the reset button and began working remotely between Jamaica and Houston. I needed my feet to spend a certain amount of time on American soil; better still, it’s where my aging mother, one of my sisters and, now, my daughter are planted, too. So, I live in hot and hotter locales, do my work, travel easily internationally from Houston, and soak up quiet time on the beach in Jamaica.
Ain’t life—and technology—grand!?