The Remote Islander
by Sacha
Latest episode
Is Virtual Assistant Work Right for You? Honest Talk with The VA…
Is Virtual Assistant Work Right for You? Honest Talk with The VA…
About this podcast
A podcast for remote workers, digital nomads and anyone dreaming of a location-independent lifestyle.
Episodes
The newest 20 of 33 episodes
- Is Virtual Assistant Work Right for You? Honest Talk with The VA Mom, Desi-Ann Gordon · 1 h 23 min · Episode 31Ever wondered if your organizing skills could become a business that serves clients around the world, from home? Remote Islanders, this one is for every boss organizer out there…
- Remote work Gatekeeping called OUT! (Ep. 30) · 12 min · Episode 30What 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…
- Pick, Choose, Refuse: The Remote Career Krishna Dewor Built (Ep. 29) · 1 h 12 min · Episode 29Ever 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…
- Remote Work From the Other Side: What Employers Actually Want (with Tahirah Webster-Banks) (Ep. 28) · 1 h 6 min · Episode 28What 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…
- The Real Reason Caribbean Professionals Aren't Getting Remote Jobs (Ep. 27) · 31 min · Episode 27The Caribbean has genuine remote work advantages: English fluency, cultural alignment with North America, strong technical education, so why isn't the opportunity converting at…
- How to Pay Your Taxes as a Remote Worker in Jamaica | ft. Colette Guthrie (Ep. 26) · 42 min · Episode 26If 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…
- Don't Let Your Location Limit You - Stories from a Remote Work Pro, Stephen Stanbury (Ep. 25) · 1 h 36 min · Episode 25Nine 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…
- 7 Remote-First Companies That Hire Globally — Including Where You Are (Ep. 24) · 20 min · Episode 24Seven 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…
- Stop Applying to the Wrong Jobs — Remote Work Guide for Caribbean Professionals (Ep. 23) · 18 min · Episode 23Stop 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…
- From Survival Mode to Remote Career: Oshido Christie on Careevo's Method (Ep. 22) · 59 min · Episode 22Landing 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…
- How to Get Hired by BairesDev in 2026: Caribbean & LatAm Guide (Ep. 21) · 10 min · Episode 21BairesDev is still one of the best doors into USD-paying remote work from the Caribbean — but the way in has changed, and most applicants don't know it. In this episode, I break…
- From Fired to Hired: Pris vs. The Remote Job Market (Ep. 20) · 1 h 21 min · Episode 20Lost your remote job? Here's how one Caribbean professional went from contract terminated to new retainer client — in under a month. Priscilla McClure (aka Pris vs. The World) is…
- AI & Remote Work: What Caribbean Professionals Must Know in 2026 (Ep. 19) · 14 min · Episode 19AI is reshaping remote work fast — and if you're a professional in the Caribbean or Latin America, you need to know exactly where you stand. In this episode, we break down the AI…
- Building the Burnout-Proof Year (Ep. 18) · 10 min · Episode 18Happy (late) New Year, Islanders! We are almost to the end of the first chapter of 2026, and if you’re already feeling "winded," you aren't alone. While the rest of the world is…
- Coaching, Co-working and Community: A conversation with Crisha Sarah Bowen (Ep. 17) · 45 min · Episode 17In the episode, I interview Crisha Sarah Bowen about her 10-year journey as a coach, her unique path to starting a co-working space, and her message of "living in your purpose"…
- From 200 Resumes to Remote Success: Crystal Duncan's Journey (Ep. 16) · 38 min · Episode 16In this episode, I talk with my longtime friend, Crystal Duncan, about the power of support systems in a remote career. Crystal, who has served as a cheerleader and guide to many…
- Beyond the Screen: Strategies for Remote Career Growth (Ep. 15) · 22 min · Episode 15Wondering how to level up your remote work career? In this episode of The Remote Islander, we dive into the strategies for career growth when you're working remotely. We cover…
- The Complete Remote Worker's Guide: The Technical Toolkit (Ep.14, P. 2) · 15 min · Episode 14Level up your remote work game in the second part of our "Complete Remote Worker's Guide"! This episode, "The Technical Toolkit," focuses on the essential hard skills and digital…
- The Complete Remote Worker's Guide - The People Side of Remote Work (Ep. 14, P. 1) · 18 min · Episode 14Dive into the essential human elements of working from anywhere in the first part of our "Complete Remote Worker's Guide"! In this episode, "The People Side of Remote Work," we…
- Unlock Productivity: Mastering Your Home Office (Ep.13) · 15 min · Episode 13Are you feeling uninspired or unproductive in your home office? You're not alone! Your workspace plays a HUGE role in your daily focus and overall wellbeing. In this episode, we…
