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.

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.

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.