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NOMADS 50+

NOMADS 50+

By: Chris Kalaboukis
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Welcome to the Nomads50+ Podcast, where we explore the freedom, adventure, and opportunities waiting for you as a digital nomad over 50. Whether you’re just starting your journey or you’re already living life on the move, this podcast is your ultimate guide to thriving on the road.Chris Kalaboukis Social Sciences Travel Writing & Commentary
Episodes
  • Ep. 45 A Decade Ahead of the Curve: Christine’s 10+ Years as a Digital Nomad | Nomads 50+
    Jan 27 2026

    Get more inspiration: https://nomads50plus.comConnect with Christine: https://www.linkedin.com/in/christinespagnuolo/---In this episode of Nomads 50+, host Chris Kalaboukis sits down with Christine Spagnuolo, a digital nomad who has been living and working remotely for over a decade—long before remote work became mainstream.Christine shares how her love of travel started early, from her first trip to Mexico at age 12 to extended adventures across the Caribbean and Thailand after university. That passion eventually shaped her career path, leading her into recruiting—where commission-based work taught her an important lesson: she didn’t need an office to succeed.She walks through the transition from agency life to running her own fully location-independent business, and how the pandemic helped normalize a lifestyle she had already been living for years. Christine also gets practical about the realities of nomad work—navigating time zones, choosing when and where to work, and why she prefers being based in Europe to align her mornings with productivity before North American clients come online.The conversation dives into the complex (and often misunderstood) topic of taxes and residency. With multiple citizenships and years on the road, Christine shares how she’s restructuring her tax setup and exploring options like Panama and Paraguay—offering valuable perspective for long-term nomads thinking beyond short stays.Christine is also candid about the broader impact of digital nomads on popular destinations. She talks about rising costs, the importance of supporting local businesses, and why seeking out less-crowded locations can lead to more authentic experiences—for travelers and communities alike.Her message to listeners is simple but powerful: don’t let fear or limiting beliefs keep you stuck. You don’t have to commit forever—just try it for a month and see what’s possible.💬 Subscribe on Substack or YouTube for more honest conversations with experienced nomads over 50 who are redefining work, freedom, and what a “normal” life can look like.

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    57 mins
  • Ep.44 Building Freedom First: Ophir’s Digital Nomad Life Across 10 Countries | Nomads 50+
    Jan 20 2026

    Get more inspiration: https://nomads50plus.comConnect with Ophir: https://www.linkedin.com/in/ophir-tal/---In this episode of Nomads 50+, host Chris Kalaboukis speaks with Ophir Tal, a digital nomad and LinkedIn ghostwriter who has spent the past two years living and working remotely across 10 different countries. Ophir’s story is a reminder that the nomadic lifestyle works best when it’s built on a solid, sustainable business—not just a love of travel.Ophir shares how his passion for independence was sparked by a long road trip across the United States in 2017, and how his girlfriend later introduced him to the idea of digital nomadism. When the pandemic made remote work possible, he was ready. Having already built his LinkedIn ghostwriting and coaching business as a side hustle while working at an NGO, Ophir transitioned smoothly into full-time remote work.He walks through the practical realities of nomad life: spending two to six months in each country, managing clients across time zones, and being transparent with clients about his lifestyle. Rather than being a drawback, he’s found that openness actually builds trust—especially with founders and solopreneurs who are already comfortable working remotely.Ophir also shares insights from the road, including why Thailand remains his favorite destination for affordability, community, and quality of life, and what to look for when choosing digital nomad hubs, co-living spaces, and co-working environments. He’s candid about safety considerations and the importance of having reliable insurance and banking systems in place.His advice for aspiring nomads is clear and practical: focus on building a location-independent income first. The lifestyle comes second. Get the work right, make sure it’s sustainable long-term, and then let travel support your life—not the other way around.💬 Subscribe on Substack or YouTube for more conversations with nomads over 50 about building freedom, flexibility, and meaningful work anywhere in the world.

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    57 mins
  • Ep. 43 Life at Sea: Linda’s 14-Year Journey as an OG Digital Nomad | Nomads 50+
    Jan 13 2026

    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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    56 mins
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