The Remote Islander
A podcast for remote workers, digital nomads and anyone dreaming of a location-independent lifestyle.
Episodes
32 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...
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...
How to Get Hired by BairesDev in 2026: Caribbean & LatAm Guide (Ep. 21)
BairesDev 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 down the 2026 version of BairesDev: what's new in their appl...
From Fired to Hired: Pris vs. The Remote Job Market (Ep. 20)
Lost 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 a Jamaican copywriter and marketer who built her entire rem...
AI & Remote Work: What Caribbean Professionals Must Know in 2026 (Ep. 19)
AI 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 conversation honestly. No hype, no fear-mongering — just a ...
Building the Burnout-Proof Year (Ep. 18)
Happy (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 watching their resolutions gather dust, the "Burnout Beast" is alr...
Coaching, Co-working and Community: A conversation with Crisha Sarah Bowen (Ep. 17)
In 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". Crisha details her spontaneous start in coaching in 2015 , how she...
From 200 Resumes to Remote Success: Crystal Duncan's Journey (Ep. 16)
In 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 new remote workers, shares the detailed advice she gives to peopl...
Beyond the Screen: Strategies for Remote Career Growth (Ep. 15)
Wondering 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 how to stay visible to management, proactive...
The Complete Remote Worker's Guide: The Technical Toolkit (Ep.14, P. 2)
Level 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 tools that empower efficient and effective remote pro...
The Complete Remote Worker's Guide - The People Side of Remote Work (Ep. 14, P. 1)
Dive 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 unpack the crucial soft skills that define remote succe...
Unlock Productivity: Mastering Your Home Office (Ep.13)
Are 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 dive deep into the world of workspace optimization, of...
More Done with Less Stress: Mastering Your Time, Wherever You Are (Ep. 12)
Drowning in deadlines and distractions? You're not alone! This week on The Remote Islander, we're tackling the universal challenge of time management. Discover practical strategies to regain control of your schedule, find b...
Work-Life Harmony: Finding Your Rhythm (Ep.11)
Maintaining work-life balance in a remote setting can be challenging!This week's episode of The Remote Islander offers actionable strategies for developing a daily routine that fosters productivity and well-being. We cover ev...
Remote, Real, & Running a Business: Kieran Khan's story (Ep. 10)
Listen in for a candid conversation with Kieran Khan, a remote work veteran and multifaceted entrepreneur! In this episode, we dive into Kieran's unique approach to time management, productivity, and navigating multiple careers.&nbs...
Thinking of going remote? Ask yourself THIS! (Ep. 9)
Thinking of trading in the office for remote work? 🌴💻 This week on The Remote Islander podcast, we drop the essential questions to ask yourself: Is remote work really for you? Self-discipline, isolation, tech sk...
Island Dreams, Remote Realities - With Debra Paul-Burgess (Ep. 8)
Tune in to my recent chat with Debra Paul-Burgess! We discuss the transition to remote work, finding balance, and how to stay productive from home. Perfect for anyone navigating the remote work lifestyle.Catch the episode to ...