The Remote Islander

What if the real gap between you and a remote job isn't information, it's action? This episode, I'm getting into something that's been on my mind for a while: the claim that Caribbean remote work voices like Krishna Dewor, Priscilla McClure, and Oshido Christie are gatekeeping opportunities from the rest of us. Spoiler: they're not, and I'll walk you through what's actually happening instead. In this episode: Why the "gatekeeping" label gets thrown at career creators everywhere,...

Ever wondered how to get to a point in your career where you can CHOOSE your next job? Krishna Dewor has the answer. Krishna is a Client Support Concierge based in Kingston, Jamaica, with eight years of remote work under his belt. He was one of the amazing speakers at the first Caribbean Remote Work Conference in June, where thousands tuned in for his breakdown of what actually makes a resume work. In this episode, we get into it all: over-communication as a remote work superpower, why...

What does it actually take to get hired for a remote job, straight from the person on the other side of the table making the hiring decisions? This week I sit down with Tahirah Banks-Webster, founder and strategist from Anguilla who runs AlphaNorth Global and ShipSmart Logistics. Unlike most guests on the show, Tahirah isn't looking for remote work, she's the one doing the hiring, building and leading distributed teams across the Caribbean and the US. She pulls back the curtain on exactly wha...

The Caribbean has genuine remote work advantages: English fluency, cultural alignment with North America, strong technical education, so why isn't the opportunity converting at scale? In this episode, I break down the real, data backed reasons the Caribbean remote work gap exists, and it's not the reason most people think. From IMF brain drain figures to a LinkedIn presence problem that's bigger than anyone admits, this is a no fluff look at what's actually holding Caribbean profession...

If you're earning money from a foreign employer and living in Jamaica, you have a tax obligation - and it's yours to manage, not your employer's. In this episode, I sit down with Colette Guthrie, a tax professional at PriceWaterhouseCoopers Jamaica, to break down exactly what Jamaican remote workers need to know about paying their taxes correctly. We cover: How tax residency works and why it means you're taxed on your worldwide incomeThe four statutory deductions every self-employed rem...