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Charles Wheatley began his career in education as a class teacher in February 1955 in East End Methodist School. He served as a head teacher of North Sound Methodist School, West End Methodist School, Cane Garden Bay Methodist School, East End Methodist School, and Road Town Elementary School. He was the first local principal of the British Virgin Islands High School, chief education officer, and the permanent secretary for the Ministry of Health, Education, and Welfare. He left that position to serve as president of the H. Lavity Stoutt Community College for the next fourteen years, where he is president emeritus. He is also the author of Voices and Visions of Education Heroes, Leaders, and Elders: A History of Education in the British Virgin Islands.