Carole Jean Connolly graduated college with a teaching degree in physical education. While searching the want ads for a teaching job, she stumbled upon a job working in a Disco in the Virgin Islands and decided to sow her wild oats before settling down to a stable life of teaching and raising a family in the suburbs. She was hired by Trans International Airlines in 1973 and flew until 1980.
She worked as a California real estate agent while raising two children, and lived in Santa Cruz, California until they graduated college. Adventure beckoned and she moved to the Virgin Islands to work on a charter sailboat as the first mate and chef. She wrote a monthly column for “Crew Life” about her sailing adventures and continues to write stories of her colorful life on her popular blog, “Carole Jean’s Capers.”