The Remote Islander

Sacha
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A podcast for remote workers, digital nomads and anyone dreaming of a location-independent lifestyle.

  1. APR 24

    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 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 scriptHow Careevo's Job Alignment Tool helps you apply smarter, not harderWhat the Authority Suite is and who it's built forThe Caribbean Remote Job Board: a centralised hub coming to change the gameReady 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: 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.

    59 min

  2. APR 17

    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 being hired in 2026 — including non-technical roles in HR, marketing, and financeWhy Caribbean professionals have a structural nearshore advantage5 practical tips to sharpen your application right nowThe truth about the talent bench and what silence really meansReady to go remote? Start at theremoteislander.com 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.

    10 min

  3. APR 10

    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 timeHow to stand out in interviews by showing up like you're already on the teamWhy your LinkedIn profile is your remote work marketing page — and what Caribbean professionals are missingUsing AI in your content and job search without sounding like a robotBuilding your personal brand now so opportunities find you before you go lookingVisit 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: 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.

    1h 21m

  4. MAR 30

    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 agents — and why it matters for how you workWhich jobs and tasks are genuinely at risk (and which aren't)Why multilingual AI is a game-changer for our regionThe cultural bias problem in AI — and your role as a cultural editorConcrete steps to future-proof your remote career starting todayReady 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: 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.

    14 min

  5. MAR 1

    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 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.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.

    10 min

  6. 11/28/2025

    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 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/ 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.

    45 min

  7. 11/19/2025

    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 its referral program but you can sign up for an account here.

    38 min

  8. 06/11/2025

    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 control of your career trajectory and thrive in the remote 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 you can sign up for an account here.

    22 min
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About

A podcast for remote workers, digital nomads and anyone dreaming of a location-independent lifestyle.

Information

  • Creator
    Sacha
  • Years Active
    2024 - 2026
  • Episodes
    24
  • Rating
    Explicit
  • Copyright
    © 2026 The Remote Islander
  • Show Website
    The Remote Islander