Mentoring Cayman Celebrates Another Year of Transforming Lives and Building Cayman’s Future

For more than two decades, Mentoring Cayman has been quietly shaping the future of the Cayman Islands by creating relationships that nurture and strengthen the next generation of leaders.

The Cayman Islands Chamber of Commerce recently celebrated the conclusion of its 2026 Mentoring Cayman programme with a Closing Reception at the Intergenerational Hub, bringing together mentors, mentees, parents, educators, sponsors and community partners to recognize a year of growth, achievement and connection.

While the reception marked the end of another six-month mentoring cycle, it also served as a reminder of the extraordinary impact the programme has had since its launch in 2002. Established in partnership with the Ministry of Education, Mentoring Cayman was the first structured mentoring programme of its kind in the Cayman Islands and has since created more than 1,000 mentor-mentee relationships.

Over the years, the programme has connected high-achieving students with experienced professionals from business, government and the wider community, providing guidance that extends far beyond career advice. Mentors share lessons learned through success and failure, helping young people build confidence, develop leadership skills, make informed life decisions and broaden their understanding of what is possible.

The programme’s influence can be seen not only in the lives of individual mentees, but across the wider community. Former participants have gone on to become accountants, entrepreneurs, managers and community leaders, while some have returned to support the next generation through mentoring and volunteer service of their own. Mentoring Cayman has also helped establish the value of structured youth mentoring in the Cayman Islands, paving the way for other initiatives and contributing to a stronger culture of community engagement and youth development.

Speaking at the reception, Chamber President Cristina Spratt reflected on the importance of giving young people meaningful exposure to career opportunities and real-world experiences.

“Throughout the year, mentors and mentees have had the opportunity to spend time together, discuss opportunities, gain a deeper understanding of different professions and get hands-on experience,” she said. “It gives young people the chance to ask themselves: ‘Is this what I want to do? Is this the path I want to take?’ That kind of insight is invaluable as they begin making decisions about their future.”

Long-time mentor Mary Reynolds, who returns year after year to support the programme, said the experience is equally rewarding for those providing guidance.

“I learn so much from my mentees,” she said. “This is the fifth mentee that I’ve had, and each one is a different experience. Each one brings their own perspective and culture to the table, which I love.”

Reynolds said she encourages students to make the most of the opportunities available to them.

“I always tell my mentee on the first day that this programme is what they make of it. Its purpose is to expose them to different things and get them outside the classroom and into a real-world setting. That experience is incredibly important. The things they learn, the experiences they share with their families, and even a small spark of inspiration can stay with them for the rest of their lives.”

For many participants, the programme helps turn uncertain ideas into clearer ambitions.

Mentee Zaina Doctor said the experience provided valuable insight into the legal profession through her mentor, Jackie Doak.

“I’ve learned a lot, especially about law, because my mentor is a lawyer and I’ve been able to see what Jackie does on a day-to-day basis,” she said. “I came into this experience unsure about the type of law I wanted to pursue, but by seeing what she actually does, I was able to narrow down my interests and gain a much better understanding of the profession.”

Mentor Roger Southam of My Realtor said his approach is centred on helping students pursue their own ambitions.

“I want to know where they want to go, what they want to be and what they want to achieve. It’s all about what they want.”

Southam described helping his mentee, Summer, pursue her interest in actuarial science by connecting her with professionals who could provide advice, inspiration and real-world perspectives.

For many participants, the relationships formed during the programme continue long after the formal mentorship ends.

Former mentee Diedre reflected:

“Over the weeks we got really close and I learnt a lot.”

In her closing remarks, Programmes Coordinator Jada Ramoon celebrated the transformation she witnessed throughout the year.

“We didn’t just witness a programme take place over the last few months; we witnessed transformation. We saw doubt turn into confidence, curiosity turn into ambition, and potential into pure leadership.”

The Chamber extends its sincere appreciation to sponsors Rocky’s Diamond Gallery, Cayman Water Company Limited and the Maritime Authority of the Cayman Islands (MACI) for their valued support and commitment to the programme.

As Mentoring Cayman enters its third decade, its mission remains unchanged: connecting experience with potential and building stronger leaders, stronger businesses and stronger communities for the Cayman Islands.