The Remote Islander

Remote work Gatekeeping called OUT! (Ep. 30)

Fri, 14 Aug 2026 00:00:00 -0400

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's actually happening instead.

In this episode:

Why the "gatekeeping" label gets thrown at career creators everywhere, not just here
What competing in a truly global remote job market actually looks like
The nine months it took me to land my next role after sixteen years in an office
Seven concrete moves to make this week if you're serious about landing remote work
The one thing most people skip: actually asking for help

Head to theremoteislander.com for more tools to help you land your next remote role.
Also check out the Global Caribbeans job board and the recap of the Caribbean Remote Work Conference 2026

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.

Pick, Choose, Refuse: The Remote Career Krishna Dewor Built (Ep. 29)

Fri, 31 Jul 2026 00:00:00 -0400

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.

In this episode, we get into it all: over-communication as a remote work superpower, why your resume needs to change for every single job you apply to, debunking "gate-keeping" and why AI and no-code tools like Zapier are becoming must-have skills, not nice-to-haves.

What we cover:

How Krishna went from a hybrid role to fully remote, and why the commute was the final straw
The real meaning of ATS and why your resume gets filtered before a human ever sees it
Zendesk, Salesforce and the no-code tools worth learning even if you're not "technical"
What to do to take your remote career to the next level - pick, choose and refuse jobs on your own terms

Listen to the full conversation and check out more resources at theremoteislander.com.

Guest: Krishna Dewor, Client Support Concierge, Kingston, Jamaica
Connect with Krishna on LinkedIn

Remote Work From the Other Side: What Employers Actually Want (with Tahirah Webster-Banks) (Ep. 28)

Fri, 24 Jul 2026 00:00:00 -0400

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.

In this episode:

Tahirah's three-part hiring process, and why LinkedIn's "good fit" score isn't the whole story
The instant disqualifiers most candidates don't even know about
Why trust is the real barrier to tech adoption in the Caribbean, and how to build it
What actually makes a remote candidate stand out (hint: it's not your degree)
The home workspace habits that signal you're ready for remote work

If you're serious about landing a remote job, this is the episode that shows you exactly what's happening on the other side of the screen. Head to theremoteislander.com for more.

The Real Reason Caribbean Professionals Aren't Getting Remote Jobs (Ep. 27)

Fri, 17 Jul 2026 00:00:00 -0400

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 get a degree" advice is outdated for global hiring
The truth about ATS systems and why 92% of recruiters aren't auto-rejecting your resume
Why your location filter might be quietly killing your job search
The staggering LinkedIn visibility gap facing Caribbean professionals
What Latin America's remote work boom can teach (and warn) the Caribbean

Ready to stop guessing and start strategizing your remote career? Head to theremoteislander.com for more episodes, resources, and real talk on building a global career from home.

How to Pay Your Taxes as a Remote Worker in Jamaica | ft. Colette Guthrie (Ep. 26)

Tue, 09 Jun 2026 00:00:00 -0400

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/

Don't Let Your Location Limit You - Stories from a Remote Work Pro, Stephen Stanbury (Ep. 25)

Mon, 01 Jun 2026 00:00:00 -0400

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/

7 Remote-First Companies That Hire Globally — Including Where You Are (Ep. 24)

Mon, 25 May 2026 00:00:00 -0400

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.

Stop Applying to the Wrong Jobs — Remote Work Guide for Caribbean Professionals (Ep. 23)

Fri, 08 May 2026 00:00:00 -0400

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 to use them smarter
9 international remote job boards that genuinely mean worldwide
Caribbean-specific platforms you probably haven't bookmarked yet
How to spot scams before they waste your time
How to get paid in USD from the Caribbean (Wise, PayPal, Payoneer and more)
A 6-step action plan to execute this week, completely free

Your remote career starts with the right map — head to theremoteislander.com for more resources to help you get there.

From Survival Mode to Remote Career: Oshido Christie on Careevo's Method (Ep. 22)

Fri, 24 Apr 2026 00:00:00 -0400

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 episode:

Why mindset is the biggest barrier to landing a remote job (and what to do about it)
The 3-part positioning system: resume, LinkedIn, and intro script
How Careevo's Job Alignment Tool helps you apply smarter, not harder
What the Authority Suite is and who it's built for
The Caribbean Remote Job Board: a centralised hub coming to change the game

Ready to start your remote career journey? Head to theremoteislander.com

Guest: Oshido Christie, Remote Career Strategist & COO at Careevo TikTok/Instagram: _.oshido._ | LinkedIn: Oshido Christie | YouTube: https://www.youtube.com/@UC387mOsaN5rNkRGmm-1fXEA

How to Get Hired by BairesDev in 2026: Caribbean & LatAm Guide (Ep. 21)

Fri, 17 Apr 2026 00:00:00 -0400

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 works
Who's being hired in 2026 — including non-technical roles in HR, marketing, and finance
Why Caribbean professionals have a structural nearshore advantage
5 practical tips to sharpen your application right now
The truth about the talent bench and what silence really means

Ready to go remote? Start at theremoteislander.com

From Fired to Hired: Pris vs. The Remote Job Market (Ep. 20)

Fri, 10 Apr 2026 00:00:00 -0400

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 time
How to stand out in interviews by showing up like you're already on the team
Why your LinkedIn profile is your remote work marketing page — and what Caribbean professionals are missing
Using AI in your content and job search without sounding like a robot
Building your personal brand now so opportunities find you before you go looking

Visit theremoteislander.com for more resources on building your remote career from the Caribbean.

Guest: Priscilla McClure — Copywriter, Content Marketer & Remote Work Creator 📱 TikTok/Instagram: @prisvstheworld | LinkedIn: Priscilla McClure | YouTube: https://www.youtube.com/@prisvstheworld

AI & Remote Work: What Caribbean Professionals Must Know in 2026 (Ep. 19)

Mon, 30 Mar 2026 00:00:00 -0400

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 agents — and why it matters for how you work
Which jobs and tasks are genuinely at risk (and which aren't)
Why multilingual AI is a game-changer for our region
The cultural bias problem in AI — and your role as a cultural editor
Concrete steps to future-proof your remote career starting today

Ready to go deeper? Visit theremoteislander.com for resources, guides, and everything you need to build your remote career from the Caribbean.

Building the Burnout-Proof Year (Ep. 18)

Sun, 01 Mar 2026 12:00:00 -0400

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 escape the 8 AM to 7 PM chair trance.
Tactical Recharges: Moving beyond the "scrolling reset" to a true sensory shift.

Resources Mentioned:

Grab the 30-Day Burnout-Proof Audit: theremoteislander.com.
Co-working in Trinidad: Visit Crisha Sarah Bowen at Purpose Spaces.
Remote Community: Join Debra Paul-Burgess on the Remotely TT Facebook Page.
Level Up Your Schedule: Listen to our previous episode on Time Management & Deep Work.

Coaching, Co-working and Community: A conversation with Crisha Sarah Bowen (Ep. 17)

Fri, 28 Nov 2025 00:00:00 -0400

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 remote work skill she learned.

Check out the episode and feel free to connect with Crisha on her socials:

IG: @crisha.sarah.bowen @purposespaces
Facebook: Purpose Spaces
Website : https://mypurposespaces.com/

From 200 Resumes to Remote Success: Crystal Duncan's Journey (Ep. 16)

Wed, 19 Nov 2025 00:00:00 -0400

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.

Beyond the Screen: Strategies for Remote Career Growth (Ep. 15)

Wed, 11 Jun 2025 00:00:00 -0400

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 control of your career trajectory and thrive in the remote landscape.

The Complete Remote Worker's Guide: The Technical Toolkit (Ep.14, P. 2)

Wed, 04 Jun 2025 00:00:00 -0400

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 current skills or build a robust foundation for a remote career, this guide to your digital arsenal is indispensable.

The Complete Remote Worker's Guide - The People Side of Remote Work (Ep. 14, P. 1)

Wed, 28 May 2025 00:00:00 -0400

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 seasoned remote pro or just starting your journey, these insights will help you build stronger relationships and thrive.

And listen to our Time Management episode: https://www.buzzsprout.com/2422922/episodes/17039914

Unlock Productivity: Mastering Your Home Office (Ep.13)

Wed, 30 Apr 2025 00:00:00 -0400

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 personalize your space for inspiration without creating clutter. Finally, we'll share some game-changing productivity hacks to help you work smarter, not harder.

Tune in to create your ultimate remote work oasis!

More Done with Less Stress: Mastering Your Time, Wherever You Are (Ep. 12)

Fri, 25 Apr 2025 00:00:00 -0400

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!

Work-Life Harmony: Finding Your Rhythm (Ep.11)

Wed, 16 Apr 2025 00:00:00 -0400

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.

Remote, Real, & Running a Business: Kieran Khan's story (Ep. 10)

Fri, 11 Apr 2025 00:00:00 -0400

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.

Thinking of going remote? Ask yourself THIS! (Ep. 9)

Fri, 04 Apr 2025 00:00:00 -0400

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!

Island Dreams, Remote Realities - With Debra Paul-Burgess (Ep. 8)

Fri, 28 Mar 2025 00:00:00 -0400

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!

My experience with WBN - An interview (Ep. 7)

Thu, 13 Mar 2025 12:00:00 -0400

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.

Beyond WFH: Exploring Remote Work Models (Ep. 6)

Wed, 22 Jan 2025 00:00:00 -0400

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!

Debunking the Digital 9-to-5 (Ep.5)

Wed, 15 Jan 2025 00:00:00 -0400

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.

Remote work reality: A guide to landing your ideal job (Ep.4)

Wed, 08 Jan 2025 00:00:00 -0400

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.

From Island Paradise to Digital Workplace: A Work Better Now Story (Ep.3)

Wed, 18 Dec 2024 00:00:00 -0400

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!

Remote Work with BairesDev: A Caribbean Perspective (Ep.2)

Wed, 11 Dec 2024 00:00:00 -0400

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.

From Corporate Cubicle to Virtual Professional (Ep.1)

Thu, 05 Dec 2024 03:00:00 -0400

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.

The Remote Islander - Trailer

Sun, 01 Dec 2024 12:00:00 -0400

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 strategies
Digital nomad life
Financial independence
Cultural experiences
Community building

Tune in to break down the barriers and discover the incredible potential of remote work in the Caribbean and Latin America.