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 income
• The four statutory deductions every self-employed remote worker must account for
• How to set up your account with Tax Administration Jamaica (TAJ) and file as self-employed
• Deductible business expenses — including your internet and phone
• The biggest mistakes people make when filing (and how to avoid them)

Head to theremoteislander.com for the full Jamaican Remote Worker Tax Guide, a free resource to go alongside this episode.

Guest: Colette Guthrie — Tax Professional, PwC Jamaica

LinkedIn: https://www.linkedin.com/in/colette-guthrie-adit-03558062/

Instagram: @thoughtstothewise

Facebook: https://www.facebook.com/share/18ceCDK36F/

You can find all of our links here:
https://linktr.ee/theremoteislander

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.

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 termination two months into his first job to becoming a Director of Operations at a fully remote company — all built on grit, Fiverr voiceovers recorded from his closet, and a refusal to let his Caribbean location be a ceiling. In this episode, Stephen unpacks what the remote work landscape really looks like in 2026, what mistakes Caribbean professionals keep making, and why your LinkedIn profile might be the most important job application you never sent. He also shares the story behind his new venture, Foundpreneur — a platform dedicated to spotlighting Caribbean entrepreneurs on a global stage.

What we cover:

• How Stephen went from freelancing on Fiverr (using his company's internet) to Director of Operations — and what it really takes to climb in remote work
• Why your LinkedIn profile, personal brand, and AI searchability are now more important than your resume
• How to stand out in a global applicant pool when everyone has an AI-optimised CV
• The Caribbean Remote Work Conference 2026 — and why you need to be there

Ready to build your remote career on your own terms? Head to theremoteislander.com for resources, episode notes, and more.

Guest: Stephen Stanbury — Remote Work Veteran, Personal Branding Strategist, and Founder of Foundpreneur | Find him on LinkedIn: https://www.linkedin.com/in/stephenstanberry/

You can find all of our links here:
https://linktr.ee/theremoteislander

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.

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.

Not companies that "allow" remote work - companies where remote is the foundation.

From the creative-as-a-service world of Superside to the radical salary transparency of Buffer, this is your no-fluff shortlist of employers who have already built the infrastructure to hire you, pay you, and support you across borders.

Key topics covered:

• Why remote-first culture matters more than remote-friendly policy — and how to tell the difference
• Automattic, GitLab, Zapier, Superside, SafetyWing, Remote.com, and Buffer: what each company does and what to expect going in
• Why written English is your competitive advantage — and how to sharpen it before you apply
• Three practical principles for actually landing a role at any of these companies

Ready to take your remote career seriously? Start at theremoteislander.com.

You can find all of our links here:
https://linktr.ee/theremoteislander

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.