The Remote Islander
A podcast for remote workers, digital nomads and anyone dreaming of a location-independent lifestyle.
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 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, building and leading distributed teams across the Caribbean and the US. She pulls back the curtain on exactly what employers are really looking at when your application lands in front of them.<...
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 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's bigger than anyone admits, this is a no fluff look at what's actually holding Caribbean professionals back, and what to do about it starting today.
In this episode you'll learn:
Why the "just g...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 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 incomeThe four statutory deductions every self-employed remote worker must account forHow to set up your account with Tax Administration Jamaica (TAJ) and f...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 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...
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.
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 re...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-only buried in line four of the description, this episode is for you. I break down the actual platforms, search strategies, and scam red flags — no fluff, no gatekeeping — categorized by industry so you can move fast and move smart.
In this episode:
Why LinkedIn and Indeed fall short for Caribbean job seekers — and how...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 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 Etsy to building a full ecosystem — job board, AI-powered tools, and coaching — designed to keep Caribbean professionals home while earning what they deserve. No fluff, no gatekeeping — just the real process.
In this...
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 application process, who they're actually hiring (hint: it's not just developers), and how Caribbean and Latin American professionals can position themselves to stand out in a pool of over 2.4 million applicants a year. Straight facts — what you need to know before you apply.
What's covered:
How BairesDev's AI-driven talent matching system actually worksWho's bein...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 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-nonsense strategy she used to land a new opportunity before most people even update their resume.
Key topics covered:
Why "quality over quantity" wins the remote job search every ti...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 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 Caribbean and LATAM professionals specifically. This is the episode that turns confusion into strategy.
What we cover:
The difference between AI tools and AI 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 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 just being tired. We’re diving into:
The "Sunday Scaries" on a Tuesday: Why your nervous system might be in a constant "threat response".The "Blur": How to e...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 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 about her the three-level vision for Purpose Spaces: Social, Working, and Events, why the concept of slow growth was more beneficial than the "massive, quick growth" she originally wanted and the most vital...
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 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 links here:
https://linktr.ee/theremoteislander
Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test
*Edit: Payoneer has stopped i...
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, 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. We also explore effective online networking, remote-friendly professional development opportunities, and the importance of upskilling and re-skilling for long-term career resilience.
This episode is packed with actionable tips to help you take con...
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 professionals.
We explore everything from mastering project management software and optimizing your virtual meeting setup to cybersecurity best practices, cloud collaboration platforms, and leveraging automation for productivity.
Discover the must-have technical proficiencies that will not only streamline your workflow but also make you an invaluable asset in any distributed team.
Whether you're looking to enhance your...
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 success.
From mastering virtual communication and building trust with remote teams to effective time management and maintaining work-life boundaries, we cover the often-overlooked interpersonal skills that make or break your remote career.
Learn how to foster connection, stay productive without micromanagement, and navigate the unique social dynamics of the distributed workforce.
Whether you're a se...
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, offering practical, actionable tips to transform your home into a productivity powerhouse. We'll explore the crucial elements of ergonomics – from investing in the right chair (it's not just somewhere to sit!) and desk setup to understanding the impact of lighting and ambiance on your mood and focus. We'll also tackle the often-overlooked aspects of sound and acoustics, and how to...
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 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
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.
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 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 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 yo...
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.
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://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...
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 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 has stopped its referral program but you can sign up for an account here.
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 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
EF SET 15-minute test
*Edit: Payoneer has stopped its referral program but you can sign up for an account here.
My experience with WBN - An interview (Ep. 7)
Island dreams meet remote teams! 🏝️ Join me and Zoe from WorkBetterNow as we discuss my experience working remotely as well as tips to help you in your remote role.
Check out WBN on their website, Instagram and Facebook for more details on remote jobs.
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.
Beyond WFH: Exploring Remote Work Models (Ep. 6)
In this episode, we talk about the different remote work models available: Work From Home (WFH), Work From Anywhere (including Digital Nomadism), Co-working Spaces, and Remote Teams.
We discuss the pros, cons, and considerations for each model to help you find the perfect fit for your lifestyle.
Listen now and unlock the freedom of remote work!
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 bu...
Debunking the Digital 9-to-5 (Ep.5)
In this episode of The Remote Islander, we're debunking some of the most common myths about remote work.
We'll explore how to achieve work-life balance, build community, and advance your career while working from anywhere.
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.
Remote work reality: A guide to landing your ideal job (Ep.4)
Happy New Year!
In this episode, we focus on strategies for finding your dream remote job.
From leveraging job boards and networking platforms to building your personal brand and reaching out directly to companies, we cover it all. We also discuss the importance of highlighting your remote work skills and continuous learning.
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...
From Island Paradise to Digital Workplace: A Work Better Now Story (Ep.3)
Ever dreamed of working remotely for a US company from the comfort of your home 🏠?
In this episode, I talk about my personal experience working for Work Better Now (WBN). Discover how I landed the job, the ins and outs of the hiring process, and what it's really like to be a remote worker for WBN.
From the supportive company culture to the flexible work arrangements 💼, I'll share it all.
So, if you're curious about remote work opportunities in the Caribbean and Latin America🌴, tune in now!
You can find all of our links here:
ht...
Remote Work with BairesDev: A Caribbean Perspective (Ep.2)
In this episode, I share my first remote work experience at BairesDev, a leading software development company in Latin America. From the application process to the challenges and rewards of working remotely with a global team, I cover it all.
Tune in to learn more about this exciting opportunity for tech professionals and how you can make the most of remote work.
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...
From Corporate Cubicle to Virtual Professional (Ep.1)
In this inaugural episode, we dive deep into my journey from a traditional office job to the exciting world of remote work. Discover how I navigated the challenges of a toxic work environment, the leap of faith required to embrace remote work, and the unexpected twists and turns along the way.
Join me as I share a very personal experience of lessons learned and insights into the realities of remote work.
You can find all of our links here:
https://linktr.ee/theremoteislander
Links mentioned:
BairesDev
Keron Rose's Blog
E...
The Remote Islander - Trailer
The Remote Islander is your go-to podcast for all things remote work and digital nomadism in the Caribbean and Latin America. Join your host, Sacha, a Trini girl who traded the traditional 9-to-5 for the freedom of remote work. We'll delve into the exciting world of remote work, exploring the challenges, opportunities, and unique perspectives of living and working in the Caribbean and Latin America.
Whether you're a seasoned remote worker or just starting your journey, you'll find valuable insights, tips, and inspiration on topics like:
Remote work strategiesDigital nomad lifeFinancial independenceCultural experiencesCommunity buildingTune...
