[5] Though she originally intended to study theatre, Doolittle has traced her desire to work in journalism from an experience at her high school prom where she felt that the police unfairly profiled her First Nations boyfriend.

[5] After helping to cover the trial of Conrad Black in Chicago, Doolittle was hired back as a full-year intern and then a staff reporter.

[5] In 2013, Doolittle wrote a story with fellow reporter Kevin Donovan alleging that Rob Ford had been asked to leave the Garrison Ball, a military gala, because he was heavily intoxicated.

[5] Titled Crazy Town: The Rob Ford Story, the book was released in Canada and the United States in February 2014.

[8] In early February 2014, film producers Daniel Iron and Lance Samuels announced they had purchased the movie rights to Crazy Town.

At The Globe, Doolittle led a 20-month investigation which determined that 1 in 5 sexual assault cases in Canada is closed by police as "unfounded".

[13] In September 2018, the man who had raped the first victim that Doolittle interviewed for her investigation was sentenced to jail after having his case reopened.