The Remote Islander
A podcast for remote workers, digital nomads and anyone dreaming of a location-independent lifestyle.
The Remote Islander
Latest Episodes
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...
Don't Let Your Location Limit You - Stories from a Remote Work Pro, Stephen Stanbury (Ep. 25)
Nine years of remote work, two layoffs over video calls, and a journey from Jamaican radio journalist to Foundpreneur — Stephen Stanbury has seen it all, and he's not holding back.Stephen Stanbury went from getting a letter of terminatio...
7 Remote-First Companies That Hire Globally — Including Where You Are (Ep. 24)
Seven companies. Zero geographic restrictions. All hiring globally - and yes, that includes you.In this episode, I break down seven remote-first companies that are genuinely worth your time as a Caribbean or LATAM professional. ...
Stop Applying to the Wrong Jobs — Remote Work Guide for Caribbean Professionals (Ep. 23)
Stop wasting time on job boards that weren't built for you — here's exactly where Caribbean professionals should be looking for legitimate remote work that pays in USD.If you've ever applied to a "remote" job only to discover it's US-onl...
From Survival Mode to Remote Career: Oshido Christie on Careevo's Method (Ep. 22)
Landing a remote job from the Caribbean in 90 days or less — is it actually possible? This episode breaks down exactly how.Sacha sits down with Oshido Christie, Remote Career Strategist and Chief Operations Officer at Careevo, to talk ab...