Key Moments
Resa Gooding’s family-first version of “global nomad” life
Resa explains how she manages a four-kid situation across borders—two children remain in Israel while she and her partner travel, weighing costs, safety, schooling, and language.Don’t stop at “get a remote job”—show routes and realities
The summit emphasizes preparation, the different ways to access international work, and what life looks like after moving—not just landing a job.Six speakers reflect multiple nomad profiles and constraints
Each 40-minute session pairs conversation with audience Q&A to match varied starting points (teachers, founders, solo movers, single parents, families).Clear summit logistics and ways to attend
The live, online summit runs Friday, October 30 (12:00–4:20 PM AST/UTC−4) with Zoom registration for the room and options to listen/watch on Freedom 106.5 FM and YouTube.What does life look like when you build a global career while raising four children? On this week’s Digipreneur segment on CNC3’s The Morning Brew, Resa Gooding joined JW and me to discuss her family’s international journey—and why those real-life experiences belong at the centre of The Digital Nomad Summit 2026.
Viewing update: This interview was recorded before the final event arrangements. The current ways to attend are Zoom, Freedom 106.5 FM radio and Freedom’s YouTube livestream. The AI Centre option mentioned in the recording is not available.
Resa Gooding: a global career, with family in the picture
Resa Gooding’s story goes beyond packing a laptop and booking a flight. She described starting out in digital marketing, helping businesses build marketing and sales systems, and later moving into AI and emerging technologies. Her international life has meant adapting to new cultures while keeping work and family responsibilities moving.
She is a mother of four, but the family does not all travel together. In our conversation, Resa explained that two children remain in Israel while two travel with her and her partner. With the travelling family based in Sri Lanka and experience in India, she spoke about weighing living costs, safety, schooling and language—not just choosing an attractive destination.
That is what makes her perspective valuable. Building a life across borders does not remove everyday responsibilities; it changes how you manage them. Resa also reminded viewers that going abroad need not mean leaving home forever. It can be an experience for a particular stage of life.
Why the Digital Nomad Summit 2026 matters now
Across our platforms, the questions keep coming: How do I work for an international company? Can I serve clients overseas from Trinidad and Tobago? What could I build online? And if I want to move, what would that look like with my actual circumstances?
The conversation cannot stop at telling people to “get a remote job.” People need to see the different routes, the preparation involved and the realities after the move. They also need examples they can recognise themselves in.
That is why Curtis Jordan and I are bringing six Caribbean professionals together for The Digital World Presents: The Digital Nomad Summit 2026. On Friday, October 30, from 12:00–4:20 PM Atlantic Standard Time—Trinidad and Tobago time, UTC−4—we will hear from people already building careers, businesses and lives internationally.
This is not a promise that moving abroad solves every problem. Nor do you have to relocate to benefit. You can develop skills, earn from international work and serve worldwide clients while remaining in the Caribbean. Greater choice over where you live is one possible outcome, not the only goal.
THE DIGITAL WORLD PRESENTS FREE / LIVE / ONLINEYOUR NEXT CHAPTER.A WORLD OF POSSIBILITIES.THE DIGITAL NOMAD SUMMIT 2026FRIDAY, OCTOBER 30 · 12–4:20 PM AST
Six Caribbean voices. Real experiences. Your questions.RESERVE YOUR FREE ZOOM PLACE Radio and YouTube viewers do not need to register.
Six guests, six different starting points
There is no single digital nomad profile. A teacher’s decisions will differ from a founder’s. Moving alone raises different questions from relocating with a child. Our speakers reflect that range, with each 40-minute session combining a conversation and audience Q&A.
Andrea Bernard: teaching as a route into international life
12:15–12:55 PM AST. Andrea brings international education experience spanning Spain and Cambodia, alongside her work in law, entrepreneurship and advocacy. Her session is for teachers and professionals who want to understand how their existing expertise could open doors abroad. Not every international opportunity starts with a technology job; education is part of this conversation too.
Ethan Auguste: creative entrepreneurship in Bali
12:55–1:35 PM AST. Based in Bali, Ethan brings a background in events, media and community building to Kretopia, the AI-powered platform he is building for creative professionals and service businesses. His story connects creative skills with technology and international networks. For creatives wondering how their work could become a business that travels, Ethan offers a different entry point into the tech economy.
Ricqcolia Phillip: starting over as a solo woman traveller
1:35–2:15 PM AST. Ricqcolia relocated to Valencia, Spain, on a digital nomad visa while continuing to work with Caribbean clients. As a digital marketing strategist, entrepreneur and content creator, she brings both the work and everyday-life perspective. Her journey speaks especially to women considering a solo move: the independence, the decisions and the adjustments that come with creating a new home abroad.
Debbie-Ann Jollie: relocating as a single mother
2:15–2:55 PM AST. Debbie uses Da Nang, Vietnam, as her base while growing a digital business in marketing, personal branding, coaching and training. Her experience relocating with her son puts single-parent realities into the discussion. For parents who cannot separate career choices from their children’s needs, her story brings a practical perspective on building a business and a new daily life together.
Resa Gooding: global technology work and family life
2:55–3:35 PM AST. Resa will take the CNC3 conversation further, exploring how international business, AI expertise and family responsibilities fit together. Her story is relevant to experienced professionals and families asking whether a different lifestyle is possible without stepping away from their ambitions—or overlooking their children’s different needs.
Zsika Phillip: from global tech to building SpotPay
3:35–4:15 PM AST. Grenada-born and based in San Francisco, Zsika is the founder and CEO of SpotPay, a Y Combinator–backed fintech. His journey includes engineering and product work at Google and an MBA from Stanford. While Ethan connects creative entrepreneurship with technology from Bali, Zsika brings the perspective of building a career and company within a major global tech ecosystem. He will also discuss why he is building financial tools for the Caribbean.
Come with questions about your own next step
The afternoon opens with TATT CEO Kurleigh Prescod from 12:00–12:15 PM AST. After the six speaker conversations, Curtis and I will close from 4:15–4:20 PM AST. The Digital World presents the summit with partners TATT and Restore a Sense of I Can (RSC), and media partner Freedom 106.5 FM.
If you want to interact with the speakers and ask questions, register free for the Zoom room. You can also listen on Freedom 106.5 FM or watch the Freedom 106.5 FM YouTube livestream without registering.
Watch our CNC3 conversation above, then bring your questions on Friday. Whether you want to teach abroad, find international work, build a digital business or explore a move with your family, the point is to hear from people doing it—and leave with a clearer view of what your own next chapter could involve.
