GoodHeart | Kenya Wagstaffe finds sense of belonging in Jamaica

When the Throp-X Investment Conference convened its ‘I Moved Back to Jamaica’ panel, attendees heard firsthand accounts from individuals who decided to leave life abroad and invest in a future on the island. Among them was Brooklyn-born Jamaican-American entrepreneur and tour operator, Kenya Wagstaffe, whose journey back to her roots highlights the growing appeal of building not just businesses but full, meaningful lives in Jamaica.

Raised in Flatbush, Brooklyn, a neighbourhood known for its strong Caribbean influence, she grew up immersed in Jamaican culture long before she ever considered relocating. Her parents, both originally from Little London, Westmoreland, ensured that Jamaica remained a central part of her identity through family traditions, food, community connections and regular summer visits to the island.

“I grew up Jamaican,” she explained. “My parents cooked traditional Jamaican meals, our closest family friends were Jamaican, and I spent summers in Westmoreland with relatives. In many ways, Jamaica always felt like home.”

Despite building a successful career as a social worker within New York City’s public school system, she found herself increasingly drawn to Jamaica. What began as regular vacations soon became something deeper. “Whenever I came here, I felt like I could be my authentic self,” she recalled. “I didn’t have to code-switch. I didn’t have to make myself smaller to fit into certain spaces. Jamaica gave me a sense of freedom and comfort that I struggled to find elsewhere.”

Eventually, she noticed a telling pattern. Each time her vacation ended, the prospect of returning to New York became more difficult. “I was travelling to Jamaica three or four times a year, and every time I boarded a flight back to New York, I felt this deep sadness. My work was emotionally draining, my anxiety was increasing, and I realised I was happiest when I was here.” That realisation ultimately led her to make the move.

Like many, the transition was not without its challenges. Securing employment proved more difficult than anticipated. Hoping to continue working within Jamaica’s education system, she quickly discovered that finding opportunities was not as straightforward as she had imagined. Rather than becoming discouraged, she embraced a distinctly Jamaican approach to problem-solving. “I decided to create opportunities for myself,” she said. “I used my savings to purchase a vehicle and expand a business I had started during the pandemic.”

Today, she operates Soulfull Steps, a tour and transportation business that introduces visitors to authentic Jamaican experiences beyond traditional tourist attractions. Focusing primarily on solo women travellers, her business offers personalised tours throughout Negril and neighbouring communities, while creating a sense of safety and connection for visitors.

More recently, she has also entered the real estate sector, working part-time as a personal assistant to a developer in Negril, an opportunity that has introduced her to a new world of investment and development possibilities.

While her professional journey continues to evolve, it is the lifestyle changes that she values most. Living in Little London has allowed her to reconnect with nature in ways that were impossible in New York. The sounds of crickets at night, the sight of rolling hills, and the simple act of breathing fresh country air have become daily reminders that she made the right decision.

Beyond the scenery, she has also come to appreciate the everyday wellness benefits that Jamaica offers. "I feel incredibly fortunate to have access to so many natural things that improve my well-being," she said. "Whether it's the abundance of sunshine, healing herbs like guinea hen weed, which has been a lifesaver for menstrual cramps, or fresh aloe vera that helps with my dermatitis, there are so many gifts from nature here that I now have at my fingertips."

Equally meaningful has been the sense of community she has found. “In Jamaica, people genuinely look out for each other,” she explained, adding,  “Neighbours share what they have. Someone will call to tell you rain is coming, so you can take your clothes off the line. There’s a sense of connection that’s difficult to find in a large city.”

Her move has also strengthened family bonds, particularly with her father. “Growing up, he worked two jobs, so we didn’t get much time together. Now I get to spend time with him on his farm, enjoy meals together, and even get fresh produce from him regularly. That’s something I’ll never take for granted.”

Nearly two years after relocating, she believes the rewards have far outweighed the challenges. “My stress levels have decreased significantly, my health has improved, and my life feels more intentional,” she shared. “My nervous system has been more relaxed during these past 22 months than at any other point in my life.”

Her message to others considering a similar move is both practical and encouraging: visit often before leaping, build community, prepare financially, and remain open to the realities of island life. Jamaica, she shared, may require patience and adaptability, but for those seeking a slower pace, stronger connections and a richer quality of life, the investment can be transformative.

goodheart@gleanerjm.com