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From Boston to Barbados

Barbadian who left his homeland at age seven for Boston, but never left Barbados behind in his heart. After decades abroad, he answered Prime Minister Mia Mottley's powerful c...
Meet Dr. Winslow Sargeant – a Barbadian who left his homeland at age seven for Boston, but never left Barbados behind in his heart. After decades abroad, he answered Prime Minister Mia Mottley’s powerful call for 2025’s “Year of Return,” and boy, did he make it count! 🇧🇧 He is also the immediate past Chair of ICSB and a very dear friend of mine. Read his bio here.

🏖️The Island That Never Left His Heart

Since 2010, Dr. Sargeant has been making regular pilgrimages back to the stunning island nation he calls home. “From the moment I arrive, the ease of navigating through customs sets a welcoming tone,” he shares. But this wasn’t just another vacation – this was We Gatherin’ 2025, and it hit different.

We Gatherin 2025 represents a powerful call to return—a homecoming for Barbadians living in the diaspora. For my family and me, it is a meaningful opportunity to connect with relatives we’ve never met.

🏡Back to St. Philip: Coming Full Circle

Picture this: You’re seven years old, leaving behind the only home you’ve ever known in Marchfield, St. Philip. Fast forward decades later, and you’re returning not just to Barbados, but to your actual birthplace during the biggest homecoming celebration in recent memory. Talk about coming full circle!

“I still hold vivid memories of my childhood in Marchfield,” Dr. Sargeant reflects. Those early memories became the compass guiding him home.

💛What Tugs at the Heartstrings

Sure, everyone misses the gorgeous weather and beaches (who wouldn’t?), but for Dr. Sargeant, it goes deeper. “What I long for most is the culture—the warmth of the people and the conversations with fellow Barbadians.” It’s not just about the place; it’s about the people who make it home.

Adventures Across the Island

This wasn’t just a “sit on the beach” kind of trip! Dr. Sargeant packed his itinerary with island adventures:

🚢 Catamaran cruise along the west coast with those Instagram-worthy views

🚌 Epic bus tour hitting up St. Andrew, the historic Codrington College in St. John, and the dramatic coastline at Bathsheba in St. Joseph

Each stop added its own flavor to what was already shaping up to be an unforgettable journey.

📱The WhatsApp Group That Started It All

Here’s where it gets really heartwarming. After hearing Prime Minister Mottley’s stirring speech about 2025 being the Year of Return, Dr. Sargeant didn’t just book a solo trip. Nope! He and his siblings created a WhatsApp group to coordinate their return together. Because sometimes the best adventures are family adventures, and sometimes it takes a group chat to bring everyone home.

Her words resonated deeply with me and my family. Inspired by her message, my siblings and I created a WhatsApp group to begin planning our return. That initiative brought us together in Barbados in July 2025.

🎉More Than Just a Trip

We Gatherin’ 2025 wasn’t just about tourism or nostalgia – it was about connection, family, and rediscovering roots. For Dr. Sargeant and countless other Barbadians in the diaspora, it represented something profound: the chance to strengthen ties with extended family and meet relatives they’d never encountered before.

In a world that often feels disconnected, there’s something beautifully simple about a call to come home – and even more beautiful about answering it.

Based on interview responses from We Gatherin’ Interview: Winslow Sargeant Responses, July 18, 2025

About the Author:

Ayman Tarabishy
Ayman Tarabishy
Dr. Ayman El Tarabishy is the deputy chair of the Department of Management and a teaching professor of management at the George Washington University School of Business. His expertise involves entrepreneurship and creative, innovative, humane-focused practices. In addition, Dr. El Tarabishy is the president & CEO of the International Council fo...
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