Howard attended Earlwood Primary School and Canterbury Boys' High School. He won a citizenship prize in his final year at Earlwood (presented by local politician Eric Willis), and subsequently represented his secondary school at debating as well as cricket and rugby union. Cricket remained a lifelong hobby. In his final year at school he took part in a radio show hosted by Jack Davey, Give It a Go, broadcast on the commercial radio station, 2GB. After gaining his Leaving Certificate, he studied law at the University of Sydney, graduating with a Bachelor of Laws degree in 1961. Howard began working for the firm of Stephen Jaques and Stephen as a junior solicitor. In 1964, he took a trip around the world, visiting Britain, Europe, Israel, India, and Singapore. After returning to Sydney in 1965, he began working for Clayton Utz, but "lacked the university grades and the social connections to be on track for a partnership". He subsequently moved to a smaller firm, which became Truman, Nelson and Howard after he was made a partner.