The Remote Islander

Ever 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. I sat down with Desi-Ann Gordon, founder of Caribbean Virtual Assistants and known online as The VA Mom. She went from teaching math and crying in traffic to landing her first Upwork job in 2017, then built a training pro...

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, Priscilla McClure, and Oshido Christie are gatekeeping opportunities from the rest of us.  Spoiler: they're not, and I'll walk you through what&ap...

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 one of the amazing speakers at the first Caribbean Remote Work Conference in June, where thousands tuned in for his breakdown of what actually makes a resume work...

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 AlphaNorth Global and ShipSmart Logistics. Unlike most guests on the show, Tahirah isn't looking for remote work, she's the one doing the hiring, buildi...

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 backed reasons the Caribbean remote work gap exists, and it's not the reason most people think. From IMF brain drain figures to a LinkedIn presence problem that...

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...

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 close...

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 tran...

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-only buried in line four of the description, this episode is for you. I break down the actual platforms, search strategies, and scam re...

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 about what it really takes for Caribbean professionals to break into the international remote job market. Oshido shares how he went from selling resume templates on...

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 application process, who they're actually hiring (hint: it's not just developers), and how Caribbean and Latin American professionals can position...

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 remote career from scratch during COVID lockdowns. In this episode, she sits down with me to talk about losing her remote job, bouncing back fast, and the no-no...

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 clear-eyed look at what AI and AI agents actually are, what they can do for your remote career right now, and where the real structural challenges lie for Ca...

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 already knocking on the door for many remote workers. In this episode, we define what burnout looks like in 2026—hint: it’s more than...

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 manifested her exit from her full-time job in 2016 , and the unexpected challenges of managing a physical space in a Caribbean culture. We talk a...

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 people interested in WBN (WBN). She recounts her journey from thinking WBN might be a "hoax" to remote work and motherhood.  You can find all of our li...

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, proactively communicate your impact, and actively participate in virtual meetings. Learn how to identify skill gaps, embrace new challenges, and mentor others to showcase leadership....

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 professionals.  We explore everything from mastering project management software and optimizing your virtual meeting setup to cybersecurity best...

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 success.  From mastering virtual communication and building trust with remote teams to effective time management and maintaining work-life boundari...

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, offering practical, actionable tips to transform your home into a productivity powerhouse. We'll explore the crucial elements of ergonomics – from investing in...

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 balance, and achieve your goals – no matter where you're working from!  Listen now!  You can find all of our links here: https://linktr.ee/theremoteislander Link...

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 everything from setting up your workspace to time blocking and prioritizing self-care.  A must-listen for anyone navigating the remote work landscape. You can find all of...

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.  From running a media company to writing, wellness coaching, and radio hosting, Kieran shares his amazing insights.  You can find all of our links here: https://link...

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 skills... we cover it all!  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...

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 hear about her exciting and very real experiences!  You can find all of our links here: https://linktr.ee/theremoteislander Links mentioned: BairesDev Keron Rose's Blog...