Freedman began her career at "Cleo", doing work experience at the age of 19. Her first paid job in media was as "Cleo"'s beauty editor and she stayed at "Cleo" for five years working her way up to the position of features editor. She left "Cleo" in 1995 and spent several months as a freelance features writer for magazines including "Marie Claire", "New Weekly" and "Who Weekly". In 1996, aged 24 years, she became editor of Australian "Cosmopolitan" magazine, the youngest editor of "Cosmopolitan"'s 58 international editions.