The Remote Islander
A podcast for remote workers, digital nomads and anyone dreaming of a location-independent lifestyle.
The Remote Islander
Latest Episodes
Remote work Gatekeeping called OUT! (Ep. 30)
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, Priscill...
Pick, Choose, Refuse: The Remote Career Krishna Dewor Built (Ep. 29)
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 ...
Remote Work From the Other Side: What Employers Actually Want (with Tahirah Webster-Banks) (Ep. 28)
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 ...
The Real Reason Caribbean Professionals Aren't Getting Remote Jobs (Ep. 27)
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 ba...
How to Pay Your Taxes as a Remote Worker in Jamaica | ft. Colette Guthrie (Ep. 26)
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 PriceWaterhous...