On failing to complete his schooling, he was apprenticed to a baker in Mirfield, then to a store-keeper at Wath-upon-Dearne. After further efforts, including an unsuccessful attempt to launch a literary career in London, he moved north again to Sheffield in 1792 as an assistant to Joseph Gales, auctioneer, bookseller and printer of the "Sheffield Register", who introduced him into the local Lodge of Oddfellows. Accordingly, he eventually composed a song addressed to the Oddfellows. In 1794, Gales left England to avoid political prosecution and Montgomery took the paper in hand, changing its name to the "Sheffield Iris".