Ep. 43 Life at Sea: Linda’s 14-Year Journey as an OG Digital Nomad | Nomads 50+ cover art

Ep. 43 Life at Sea: Linda’s 14-Year Journey as an OG Digital Nomad | Nomads 50+

Ep. 43 Life at Sea: Linda’s 14-Year Journey as an OG Digital Nomad | Nomads 50+

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Get more inspiration: https://nomads50plus.comConnect with Linda: https://shellphonechronicles.substack.com---In this episode of Nomads 50+, host Chris Kalaboukis speaks with Linda Jackson, a true pioneer of the digital nomad lifestyle. Long before remote work became mainstream, Linda and her husband were living and working remotely from a sailing yacht—crossing oceans, navigating borders, and designing a life of freedom at sea. Fourteen years later, she’s still doing it.Linda shares how they eased into the sailing nomad life, starting with shorter trips before eventually crossing the Pacific Ocean. She opens up about the realities of life aboard a boat: constant attention to weather, maintaining and repairing their vessel, and the deep self-reliance required when you’re days—or weeks—from shore. But she also highlights the magic of arriving somewhere slowly, by sea, and truly earning each destination.The conversation dives into the practical side of long-term nomad life on the water. Linda explains how they manage visas, taxes, and logistics, maintain a U.S. mailing address, and stay connected with tools like Google Fi—proving that even a life at sea can be compatible with modern work.She also reflects on the human side of their journey. As one of the few visiting yachts in remote island communities, Linda has experienced extraordinary warmth and hospitality—but she’s also thoughtful about the environmental and cultural impacts of tourism, and why responsible travel matters more than ever.Her advice for aspiring nomads is honest and grounded: start small, think carefully about your work and communication needs, and recognize that nomad life—especially on a boat—isn’t for everyone. But for those who feel called to it, the rewards are unmatched.This episode is a powerful reminder that there are many ways to live a nomadic life—and some of them don’t involve airports at all.💬 Subscribe on Substack or YouTube for more extraordinary stories from nomads over 50 redefining freedom, work, and adventure.

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