In Launceston in 1850 Dowling launched his career as a portrait painter. He advertised that he was ‘prepared to execute portraits in oil and coloured crayons, as well as miniatures on ivory’. He claimed to be self-taught but it is believed he took lessons from Frederick Strange and Thomas Bock and was inspired by the portraits of Henry Mundy.
Dowling worked in Launceston but also took commissions in Hobart, regularly moving between the two cities. Among his portraits from this period are those of public figures such as the anti-transportation movement’s champions, W P Weston and the Reverend John West.