The Remote Islander
A podcast for remote workers, digital nomads and anyone dreaming of a location-independent lifestyle.
The Remote Islander
Remote work Gatekeeping called OUT! (Ep. 30)
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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
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