C. W. Chiplin spent his working life as a teacher, eventually rising to the position of headmaster. His teaching positions included schools in Sydney and regional New South Wales, notably Wellington, Dubbo, Narrabri, Sunny Corner and in the Hunter Valley where he served as principal of Heddon Greta Public School up until his retirement in the late-1920s. He also held the position of President of the Maitland District Teachers' Federation and was prominently identified with the Masonic Order.
In addition to his teaching commitments Chiplin wrote the lyrics to many songs, and in 1895 collaborated with Hugo Alpen on the opera Eldorado. The work was produced at Sydney's Guild hall in late October. At the time Chiplin was a teacher at the Enmore Public School.
Although newspaper reports during the late-nineteenth and early twentieth centuries record that many of his songs were performed, often by children at school concerts and at public events, only one song has to date been identified as having been published commercially - 'If Hearts Could Only Speak,' a collaboration with Edoardo Lebegott in 1901.