During her two decades at the Toronto Star, she reported from more than 20 countries, including Somalia, Yemen, Syria, Pakistan and went behind the wire at the U.S. Naval Prison, Guantanamo Bay more than two dozen times. Among her films, Shephard was the co-director and producer of the Emmy-nominated documentary Guantanamo’s Child, which premiered at the Toronto International Film Festival in 2015 and won Canada Screen Awards (CSA) for best direction and the Donald Brittain Award for Best Social or Political Program. Her film, The Perfect Story, was nominated for a CSA and won the DGC Canadian Documentary Feature Award at Calgary Film Festival in 2022. Her most recent films include, The Man Who Stole Einstein's Brain, which premiered at Hot Docs Film Festival in 2023 and the CSA-nominated The Way Out. She was the creative producer for Uyghurs: Prisoners of the Absurd and was a contributor to the Peabody Award-winning Under Fire: Journalists in Combat.

She is also a three-time recipient of the National Newspaper Award; and the Governor-General’s Michener Award for public service journalism, and the author of Guantanamo’s Child: The Untold Story of Omar Khadr, and Decade of Fear: Reporting from Terrorism’s Grey Zone. Michelle is currently co-writing a memoir for FBI agent Scott Payne, dubbed by Rolling Stone Magazine as the “Hilbilly Donnie Brasco.” He spent more than twenty years going undercover to infiltrate the Klu Klux Klan, outlaw motorcycle gangs, and a Neo Nazi accelerationist group.

Her podcast series that she has hosted and produced include Sharmini, a six-part investigation of a cold case she first covered as a cub reporter for the Toronto Star; Brainwashed, which looked at the CIA’s covert Cold War program “MK Ultra" and was nominated for an Ambie and White Hot Hate; a podcast that dove deep into the far-right terrorist group, The Base, and garnered a silver for best serialized podcast by the New York Festivals Radio Awards. She was also a writer and producer of the podcasts Unascertained; Do You Know Mordechai and The No Good Terribly Kind Wonderful Lives and Tragic Deaths of Barry and Honey Sherman. 

In 2018, Michelle joined award-winning producer Bryn Hughes in creating Frequent Flyer Films.

Michelle continues to write on foreign policy issues and terrorism for various publications and is an active volunteer and on the Board of Directors of Canadian Journalists for Free Expression (CJFE) and the Canadian Journalism Forum on Violence and Trauma.