Sherman's career began after graduating Bracebridge and Muskoka Lakes Secondary School, when he got a job as a copyeditor at a local magazine. Interested in the history of school, he eventually left to write a book.[2] The Curiosity of School: Education and the Dark Side of Enlightenment was published by Penguin Random House in 2012, and debuted on the national bestseller list.[3]
Sherman then turned to other stories. In 2014, he began investigating the disappearance of Joan Lawrence, an elderly woman from Huntsville, Ontario, who went missing under suspicious circumstances.[4] Sherman's work on a CBC documentary about the case won him a Canadian Screen Award in 2019.[5] An adapted version of the story was released on July 9 as the fourth season of Uncover, a CBC podcast. Sherman wrote and hosted the six-part series, entitled "The Cat Lady Case,"[6] and he and a friend scored the soundtrack.[7]
Sherman has written extensively for various magazines including Vanity Fair and Esquire. His subjects include politics,[8] crime,[9] mental health,[10] education,[11] and memoir.[12] Sherman also composes lyrics for the band Larch.[13]
On June 12, 2020, Sherman won a gold National Magazine Award for his story "Forged by Fire," published by The Globe & Mail's Report on Business Magazine.[14]
