Explore every episode of the podcast The Remote Islander
| Title | Pub. Date | Duration | |
|---|---|---|---|
| From Survival Mode to Remote Career: Oshido Christie on Careevo's Method (Ep. 22) | 24 Apr 2026 | 00:58:46 | |
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:
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 You can find all of our links here: | |||
| How to Get Hired by BairesDev in 2026: Caribbean & LatAm Guide (Ep. 21) | 17 Apr 2026 | 00:10:04 | |
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:
Ready to go remote? Start at theremoteislander.com You can find all of our links here: | |||
| Unlock Productivity: Mastering Your Home Office (Ep.13) | 30 Apr 2025 | 00:15:26 | |
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! You can find all of our links here: | |||
| More Done with Less Stress: Mastering Your Time, Wherever You Are (Ep. 12) | 25 Apr 2025 | 00:13:14 | |
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: | |||
| Work-Life Harmony: Finding Your Rhythm (Ep.11) | 16 Apr 2025 | 00:08:59 | |
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: | |||
| Remote, Real, & Running a Business: Kieran Khan's story (Ep. 10) | 11 Apr 2025 | 01:16:15 | |
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: | |||
| Thinking of going remote? Ask yourself THIS! (Ep. 9) | 04 Apr 2025 | 00:12:32 | |
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: | |||
| Island Dreams, Remote Realities - With Debra Paul-Burgess (Ep. 8) | 28 Mar 2025 | 00:50:40 | |
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: | |||
| My experience with WBN - An interview (Ep. 7) | 13 Mar 2025 | 00:15:07 | |
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: | |||
| Beyond WFH: Exploring Remote Work Models (Ep. 6) | 22 Jan 2025 | 00:08:52 | |
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. You can find all of our links here: | |||
| Debunking the Digital 9-to-5 (Ep.5) | 15 Jan 2025 | 00:06:04 | |
In this episode of The Remote Islander, we're debunking some of the most common myths about remote work. You can find all of our links here: | |||
| Remote work reality: A guide to landing your ideal job (Ep.4) | 08 Jan 2025 | 00:11:00 | |
Happy New Year! You can find all of our links here: | |||
| From Fired to Hired: Pris vs. The Remote Job Market (Ep. 20) | 10 Apr 2026 | 01:21:02 | |
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:
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 You can find all of our links here: | |||
| From Island Paradise to Digital Workplace: A Work Better Now Story (Ep.3) | 18 Dec 2024 | 00:13:09 | |
Ever dreamed of working remotely for a US company from the comfort of your home 🏠? You can find all of our links here: | |||
| Remote Work with BairesDev: A Caribbean Perspective (Ep.2) | 11 Dec 2024 | 00:11:49 | |
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: | |||
| From Corporate Cubicle to Virtual Professional (Ep.1) | 05 Dec 2024 | 00:08:36 | |
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. You can find all of our links here: | |||
| The Remote Islander - Trailer | 01 Dec 2024 | 00:01:15 | |
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:
Tune in to break down the barriers and discover the incredible potential of remote work in the Caribbean and Latin America. You can find all of our links here: | |||
| AI & Remote Work: What Caribbean Professionals Must Know in 2026 (Ep. 19) | 30 Mar 2026 | 00:14:19 | |
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:
Ready to go deeper? Visit theremoteislander.com for resources, guides, and everything you need to build your remote career from the Caribbean. You can find all of our links here: | |||
| Building the Burnout-Proof Year (Ep. 18) | 01 Mar 2026 | 00:10:13 | |
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:
Resources Mentioned:
You can find all of our links here: | |||
| Coaching, Co-working and Community: A conversation with Crisha Sarah Bowen (Ep. 17) | 28 Nov 2025 | 00:45:22 | |
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 You can find all of our links here: | |||
| From 200 Resumes to Remote Success: Crystal Duncan's Journey (Ep. 16) | 19 Nov 2025 | 00:37:41 | |
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: | |||
| Beyond the Screen: Strategies for Remote Career Growth (Ep. 15) | 11 Jun 2025 | 00:22:17 | |
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. You can find all of our links here: | |||
| The Complete Remote Worker's Guide: The Technical Toolkit (Ep.14, P. 2) | 04 Jun 2025 | 00:15:04 | |
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. You can find all of our links here: | |||
| The Complete Remote Worker's Guide - The People Side of Remote Work (Ep. 14, P. 1) | 28 May 2025 | 00:18:21 | |
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. You can find all of our links here: | |||