At the age of 15, after a short time in the electrical trade, in 1922 Askin joined the Government Savings Bank of New South Wales as a Clerk. However, when the Savings Bank closed due to the Great Depression in 1931, he joined the Rural Bank of New South Wales. Between 1925 and 1929 Askin served part-time as a Lieutenant in the 55th Battalion, Citizens Military Forces. On 5 February 1937 Askin married Mollie Isabelle Underhill, a typist at the bank, at Gilbert Park Methodist Church, Manly. They lived in Manly for the rest of their lives. He began his interest in politics by assisting in Percy Spender's successful campaign for Askin's local seat of Warringah as an Independent candidate at the 1937 Federal election. In 1940 Askin was appointed manager of the Bank service department, which focused on public relations. He served as vice-president from 1939 to 1940 and President from 1940 to 1941 of the Rural Bank branch of the United Bank Officers' Association.