Diane Eileen Scola was born in Rhode Island and brought up in a Roman Catholic household. Her father owned a jewelry company, and her mother was a housewife in their close-knit Italian-American family. Scola attended high school in Providence before attending Pembroke College, where she studied American civics. Upon her graduation in 1959, she was offered a job at Douglas Aircraft in Hartford. But her father wanted her to stay at home. As a woman in an Italian American family, she was not permitted to join the family business, and instead got a job at a department store in Providence.
She married a pharmaceutical representative from New York in 1960, and had two children with him. They divorced in 1964, and with two children aged 1 and 3, Scola became a schoolteacher in English. She discovered she loved teaching, and earned a Master’s degree in English from the University of Rhode Island in 1969 to supplement her career. Scola faced gender discrimination in her wages, and when she demanded to be paid as much as her male counterparts, many of whom did not have a Master’s degree, she was told to leave her position.
Looking for a career where she had opportunities to both satisfy her aspirations and earn a good wage so that she could support her daughters, she moved from a teaching career to business one. Finding that she still did not have leadership opportunities, she started her own jewelry company in 1979 with her brother. Scola divorced her second husband and financed both of her daughters' college educations on her own.