 Tom Chessell was born in Ashfield, New South Wales, and attended Newington College (1929–1931) where he started rowing.As a cox he represented Newington at the Head of the River in the 2nd IV in 1930 and the 1st VIII in the following year.Forced by the Great Depression to leave school, Chessell worked for his family's building company and studied building at Sydney Technical College.