The Department of Education (DOE) is saddened to announce the passing of Mr. Carlton Pickering. Mr. Pickering joined the Department of Education on 3 June 1996 as the first male Education Welfare Officer and only the second individual to serve in this role in Anguilla. He quickly demonstrated a natural aptitude for the work and became a valued member of the then-emerging student support services team.
Quiet, serious, and deeply respectful, Mr. Pickering brought to his role a strong sense of purpose shaped by his faith and community involvement. He served for a time as Associate Pastor at New Covenant Wesleyan Holiness Church in Stoney Ground, and this grounding was evident in his compassionate and thoughtful engagement with students and families. Many young male students—particularly those who were frequently absent from school and lacked positive male role models—were drawn to him. His influence contributed to the development of a more gender-responsive approach to education welfare services within the Department.
Among his contributions was the introduction of a Savings Club for students and their families, inspired by traditional community-based saving systems. This initiative reflected his practical approach to support and his understanding of the broader social factors affecting student participation and well-being.
Throughout his eleven-year tenure, Mr. Pickering also nurtured a deep interest in broadcasting, video journaling, and media production. He occasionally took unpaid leave to pursue this passion, which led to the establishment of Kreative Communications Network (KCN) along with its flagship programme, Anguilla Diary Magazine.
As his media work expanded, Mr. Pickering increasingly looked forward to retirement so that he could devote more time to this growing enterprise. He retired from the Department of Education in August 2007; however, this was not the end of his involvement in Education Welfare.
Even after his retirement, Mr. Pickering remained actively engaged with the work of the Education Welfare Unit, maintaining strong collaborative relationships and demonstrating an enduring commitment to student attendance and well-being.
For example, in September 2020, in observance of Attendance Awareness Month, he supported the “SOCK It to Truancy” initiative involving all six primary schools. Students were asked to attend on time and were encouraged to wear bright socks to show their commitment to timely attendance. Invited to address students at the Vivien Vanterpool Primary School, Mr. Pickering readily accepted and delivered a heartfelt message on the importance of regular and punctual school attendance. In a spirited show of support for the initiative, he spoke with his pants rolled up to display his vibrant socks, fully embracing the theme and connecting meaningfully with students.
His commitment extended beyond the event. He later recognized students at the Vivien Vanterpool Primary School who achieved outstanding attendance—95% and above—by presenting them with beautifully crafted plaques, celebrating their dedication and encouraging continued excellence.
Mr. Pickering consistently expressed a desire to remain involved in education welfare initiatives, and his continued interest and support were deeply appreciated by staff at the Education Welfare Unit and the DOE.
The Department of Education extends its sincere condolences to the family and friends of Mr. Carlton Pickering. His legacy lives on in the lives he touched and in his pioneering contribution to student support services in Anguilla.
