Childhood and early career The oldest of four siblings, Destra was raised in the community of Desperlie Crescent, Laventille in eastern Port of Spain, Trinidad and attended the St. James Secondary School where she discovered her passion for singing and music. She not only won her school's Calypso Monarch title for five consecutive years, she composed every one of her songs. At the age of 18 she joined a quartet called PSYKE which disbanded after only one year.