Humphrey Skerry began his education at Chiltern Primary School,Victoria, in 1905, at the age of six and a half. He completed grade six in 1912 and continued in the Higher Elementary School, where he gained his Merit Certificate in 1913. Skerry left school in 1914 at the age of fifteen. He then moved from Chiltern to Melbourne, where he became a clerk with the Doncaster Electric Supply Company. While working Skerry studied, sat for and passed the examinations that allowed him to become an accountant. In 1925 he established his own accountancy business in Melbourne.
Skerry was a long-term member and significant leader of the Rationalist movement in Victoria, being a member and office-bearer of various Rationalist groups from 1919 until his death. ASIO kept a security file on him, believing him to be a communist. Skerry's verse was read on ABC radio, and was praised by such people as Mary Gilmore, Alan Marshall, Clive Turnbull, Walter Murdoch and Betty Vassilieff (qq.v.). Skerry was also a student of the painting teacher Justus Jorgenson, under whose patronage he produced several noteworthy paintings. He also played the piano by ear, and became the Vice-President and Treasurer of the Soiree Musicale Chamber Music Society.
