Episodes

  • 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
  • Ep.42 From the American Dream to Slow Travel: Dr. Crystal’s Leap Into Life on the Road
    Jan 6 2026

    Get more inspiration: https://nomads50plus.substack.comConnect with Dr. Crystal: https://www.linkedin.com/in/crystalharrisphd/---In this episode of Nomads 50+, host Chris Kalaboukis speaks with Dr. Crystal, a former educator who chose to step off the traditional American path and design a life centered around slow, intentional travel. Her journey shows how even long-held dreams can resurface—and be acted on—later in life.Dr. Crystal shares how travel was always in the back of her mind, but like many, she followed the expected route after college: career, stability, and responsibility. It wasn’t until her daughter encouraged her to take a trip to London that something shifted. That single trip opened the door to discovering online communities of solo female travelers and slow travelers—many of them over 50—who were quietly living lives that felt more aligned.Instead of becoming an expat, Dr. Crystal chose full-time travel so she could remain closely connected to family in the U.S. She tested the lifestyle with extended stays in Mexico, then sold off most of her belongings and transitioned out of her teaching role in Chicago. Along the way, she explored Central America, embraced dental tourism in Costa Rica, and spent several months traveling through Europe—combining city stays with wellness retreats.Now, she’s preparing for a six-month journey through Asia, with plans to spend time in Thailand, Vietnam, and Malaysia. While excited, she’s also honest about the nerves that come with logistics, long-distance travel, and the unknown—making her story especially relatable.Dr. Crystal’s advice is refreshingly direct: don’t overthink it. Buy the ticket. Start with a short trip if you need to, be resourceful, and avoid expensive coaching programs that promise certainty. Solo travel, she says, works for both introverts and extroverts—as long as you’re intentional about community, safety, and connection.This episode is a powerful reminder that you don’t have to uproot your entire life to change it—you just have to begin.💬 Subscribe on Substack or YouTube for more stories, encouragement, and practical wisdom from nomads over 50 creating lives of freedom and intention.

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    59 mins
  • Ep. 41 From Minimalism to Meaning: Jillian’s Nomad Life of Art, Volunteering & Resilience
    Dec 16 2025

    Get more inspiration: https://nomads50plus.substack.comConnect with Jillian: https://artisticvoyages.com---In this episode of Nomads 50+, host Chris Kalaboukis talks with Jillian Amatt, who—along with her partner Chris—has been living a deeply intentional digital nomad life since 2017. Inspired by the Minimalism documentary, they sold their home, let go of the conventional path, and stepped into full-time travel powered by creativity, volunteering, and community.Jillian shares how they started house-sitting in Costa Rica and went on to travel through Europe, Africa, and beyond—funding their lifestyle through online work, mural painting, and hands-on volunteer projects. Along the way, they faced real-world challenges: being forced out of Nicaragua during a civil war, getting unexpectedly stranded in Morocco during COVID, and adapting—again and again—when plans fell apart.One of the most moving parts of the conversation centers on their time in Uganda, where they encountered a village facing severe food shortages during the pandemic. Jillian and Chris mobilized their network to raise funds for weeks of food aid and helped teach permaculture techniques so the community could build longer-term food security. What started as travel became purpose.As life shifted and family needs changed, Jillian and her partner rebalanced—spending part of the year in Canada, volunteering on a farm in British Columbia, while keeping their nomadic spirit alive through seasonal travel and creative work.Her advice for aspiring nomads is refreshingly grounded: don’t chase the *label* of “digital nomad.” Chase work you love, stay flexible, be resourceful, and let the lifestyle evolve around what actually matters to you.This is a powerful reminder that nomad life isn’t about escape—it’s about alignment, contribution, and resilience.💬 Subscribe on Substack or YouTube for more real stories from nomads over 50 building meaningful, unconventional lives around the world.

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    1 hr and 1 min
  • Ep.40 From Courtrooms to Conservation: How Saska Hayes Rebuilt Her Life Through Adventure
    Dec 9 2025

    Get more inspiration: https://nomads50plus.substack.com

    Connect with Saska: https://sheroamsshewrites.substack.com

    ---

    In this powerful episode of Nomads 50+, host Chris Kalaboukis talks with Saska Hayes, a former corporate lawyer from New Zealand who traded a thriving immigration law firm for a one-way ticket to Africa. Her story is one of courage, intuition, and transformation—proof that it’s never too late to walk away from “success” and start over in pursuit of meaning.

    At 30, Saska turned down a major government contract that would have secured her future—but locked her into a path she no longer wanted. Instead, she followed her gut, asking herself one question: Would I regret not doing this when I’m 40? The answer changed everything.

    Her first volunteer role in Tanzania turned out to be a scam—a devastating blow that could have ended her journey. But instead of quitting, Saska pivoted, returning to South Africa to take on a professional conservation internship where she learned GIS mapping, animal tracking, and ecological research. She even used her legal background to conduct an environmental impact assessment for a private reserve—showing that every skill, even from a past career, can be repurposed in unexpected ways.

    Now based in Oxford, UK, Saska balances bar work with volunteering for an asylum support organization while exploring future directions in policy, law, and conservation. She embraces uncertainty as a form of freedom, finding peace in the unfolding process rather than chasing a rigid plan.

    Her story is a reminder that sometimes you have to burn the old map to find your true path—and that “success” can mean something entirely different once you start listening to yourself.

    💬 Subscribe on Substack or YouTube for more stories of reinvention, resilience, and courage from nomads over 50 creating extraordinary second acts around the world.

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    1 hr and 1 min
  • Ep. 39 From Iran to Barcelona: Elham’s Journey to Freedom as a Digital Nomad
    Dec 2 2025

    Get more inspiration: https://nomads50plus.substack.comConnect with Elham: https://www.linkedin.com/in/elham-m-borojerdi-06bb047aHer Substack: https://elhamgrowthstudio.substack.com/---In this episode of Nomads 50+, host Chris Kalaboukis speaks with Elham Mohammadi, an Iranian digital nomad currently based in Barcelona, Spain. Elham’s story is one of courage, curiosity, and calculated risk—proof that it’s possible to build a thriving, location-independent career from anywhere in the world.Elham shares how her journey began while pursuing a PhD in business and economics, freelancing in SEO and digital marketing on the side. What started as a part-time gig quickly grew into a full-fledged remote business that gave her the freedom to explore cities across Spain—from Girona to Valencia—and finally settle in Barcelona, drawn by its creative energy and strong Iranian expat network.She talks candidly about the realities of funding a digital nomad lifestyle: building a client base, maintaining financial stability, and having an emergency fund in place before making the leap. Elham also explains Spain’s digital nomad visa requirements, including tax obligations and the balance between local and international clients.Beyond logistics, Elham highlights the emotional and social side of nomad life—how community and connection matter just as much as freedom. She shares how finding a supportive network of fellow expats helped her feel grounded and at home, even while living abroad.Her advice for aspiring nomads is practical and empowering: invest in reliable Wi-Fi, prioritize your health, keep learning new skills, and transition gradually. The key, she says, is flexibility—staying open to change while staying true to your goals.💬 Subscribe on Substack or YouTube for more inspiring stories and practical insights from digital nomads over 50 redefining work, freedom, and connection.

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    58 mins
  • Ep. 38 Prioritize Adventure: Overcoming Fear & Finding Freedom Through Travel | Nomads 50+
    Nov 18 2025

    Get more inspiration: https://nomads50plus.substack.comConnect with Mary: https://marybartnikowski1.substack.comBook a 1:1 Call with Mary: https://calendly.com/marybartnikowski---In this inspiring episode of Nomads 50+, hosts Chris Kalaboukis and Mary Bartnikowski dive deep into what it really means to make travel a priority—no matter your age, resources, or fears.Mary reflects on her early travel years, long before smartphones and travel apps made everything easy. Back then, she made it happen through hustle and heart—working extra photography jobs, cutting expenses, and saving every dollar to fund trips to places like Nepal and South America. Her message is clear: if travel is truly important to you, you’ll find a way.She also opens up about the fears and insecurities that come with solo travel—walking into a busy restaurant alone, navigating public transport in foreign countries, and learning to trust herself in unfamiliar environments. Along the way, she shares stories of cultural challenges, like being turned away from a rooftop restaurant in Mexico, and how staying open-minded, flexible, and kind can turn even awkward experiences into moments of growth.Mary and Chris explore how spontaneity and serendipity—the kind that existed before the constant connection of the internet—can still be found today if we allow space for it. They also talk about life transitions—breakups, accidents, and unexpected changes—that can serve as powerful turning points toward reinvention and renewal.Their closing message is simple but profound: decide that travel matters to you, make a plan, and take that first step. The rest unfolds from there.💬 Subscribe on Substack or YouTube for more stories, insights, and encouragement from nomads over 50 creating lives of freedom, purpose, and adventure.

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    1 hr
  • Ep. 37 Ordinary Life in Extraordinary Places: Nomad Jim’s Journey of Minimalism & Freedom
    Nov 11 2025

    Get more inspiration here: https://nomads50plus.substack.comConnect with Jim: https://www.youtube.com/@UCcel5IAFjs3wDL_nqYzX_7Q ---In this week’s episode of Nomads 50+, host Chris Kalaboukis sits down with “Nomad Jim,” a retired solo traveler who has spent the past three years living a slow, minimalist lifestyle across the globe. At 56, Jim sold his home, downsized everything he owned, and set out to create a simpler, more intentional way of life—one that prioritizes experiences over possessions.Jim shares how he planned and prepared for early retirement, including the financial and emotional adjustments that come with shifting from a traditional life to full-time travel. He explains the difference between vacationing and living nomadically, and how building daily routines, maintaining good health, and staying mentally grounded are essential to long-term travel success.One of the most fascinating parts of Jim’s story is his experience with healthcare abroad. He talks about receiving high-quality, affordable medical and dental care in Malaysia—complete with thorough screenings and attentive service—all at a fraction of U.S. costs. This has even inspired him to make Malaysia his base for annual health checkups.Jim also opens up about the beauty of slow travel and cultural immersion. From navigating language barriers with translation apps to connecting with locals over shared meals, he’s found meaning in blending into communities rather than just passing through.For Jim, the digital nomad lifestyle isn’t about adrenaline or bucket lists—it’s about living an “ordinary life in extraordinary settings.” His approach proves that a fulfilling, sustainable nomadic life after 50 is not only possible but deeply rewarding.💬 Subscribe on Substack or YouTube for more interviews, insights, and inspiration from nomads over 50 redefining what freedom looks like around the world.---MY PODCAST GEARSteelSeries Arctis Nova 7 Wireless Multi-Platform Gaming Headset https://amzn.to/3WvVImMLenovo Legion Pro 5i Gen 10 Gaming Laptop https://amzn.to/47QtlGgBlue Snowball iCE Condenser Microphone https://amzn.to/4hBWTeaInnoGear Boom Arm Microphone Mic Stand https://amzn.to/3WsEo23PQRQP 3 in 1 Wireless Microphones Wireless Lavalier Microphone https://amzn.to/47fENemLogitech Brio 4K Webcam, Video Calling, Noise-Cancelling https://amzn.to/49tocFk

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    1 hr