Doolittle began her career at the Toronto Star, covering crime and then municipal politics. While on the city hall beat, she began investigating rumours of the mayor’s troubled personal life. In 2014, the Toronto Star was awarded the prestigious Michener Award for its investigation into Rob Ford’s substance abuse. Two years earlier, Doolittle became the youngest recipient of the Mary Deanne Shears Award as the Star‘s reporter of the year. A graduate of Ryerson University’s journalism program, Doolittle was named as one of 12 notable alumni at the school’s 60th anniversary last fall. She has lived in Toronto since 2002.