 Whitfield's opera career lasted four years.Her change in orientation took her first to working as a singing cocktail waitress and then to singing in nightclubs, including the Rrazz Room and the Empire Plush Room in San Francisco, the Cinegrill in Los Angeles, The Oak Room of the Algonquin Hotel in Manhattan, and Scullers Jazz Club in Boston.In 1977, two boys approached Whitfield on a street in San Francisco and told her to go with them.