J. R. Houlding worked in a law office in London, where he met Charles Dickens. Arriving in Sydney in 1839, he then spent a year in New Zealand before returning to New South Wales. He worked in various capacities in the colony, being at one time or another a lawyer's clerk, a storekeeper, a country postmaster, a journalist, and a lay preacher. Houlding held strong Methodist beliefs, and founded a ragged school and a soup kichen in Sydney. He visited England in 1854, but encountered financial difficulties on returning to Sydney the following year and suffered a nervous collapse as a result.
While recovering, Houlding began to write fiction, producing short stories and poems under as many as 17 pseudonyms, mainly unidentified. At the instigation of John Fairfax (another devout Methodist), Houlding became a regular contributor to The Sydney Mail, where he employed his most famous writing name 'Old Boomerang'. In 1866, Houlding sent drafts of his first novel (as yet unpunctuated) to the prominent Sydney literary patron N. D. Stenhouse. Houlding was pleased with the criticism he received and printed a testmonial from Stenhouse as a preface when the work was published, as Australian Capers: or Christopher Cockle's Colonial Experience, in 1867.
Thereafter Houlding continued to write short stories and poetry, and produced several novels in which he explores the challenges of adapting to Australian conditions. Many of his works employ the theme of an innocent youth falling foul of the tricks of the cunning and worldly. Houlding's strong Methodist and temperance beliefs are also evident in much of his writing, which is often characterised by the use of metaphor, Australian idiom, and characters presented as colonial types. The great majority of his work was aimed at the young, and with their strong moral emphasis, his books were popular as Sunday school prizes.
