Hailes claimed to have been an acquaintance of several British literary figures including Sir Walter Scott, de Quincy and others, before emigrating to Australia, and he had already published a selection of his poetry, The Emigrant and Other Poems (1833). After arriving in South Australia on the Buckinghamshire in 1839 as the Superintendent of Emigrants, Nathaniel Hailes operated an auctioneering business in Adelaide. He was a colourful character, well-known for his prolific writings under the pseudonym 'Timothy Short', publishing what he later described as 'verses, generally satirical, allusive to passing occurrences' in The Register, The Southern Australian and other journals. He established the Adelaide Free Press (1841?) and with G. Dehane published the Independent and Cabinet of Amusement. In 1841 he was a member of the City Council and in 1842 was a member of the 'Provisional Committee of the Society which was formed to secure religious freedom' (Obituary)
In 1842 Hailes was faced with bankruptcy. He was appointed Clerk of the Court at Port Lincoln and Clerk to the Government Resident. He wrote for the Register on the subject of Aboriginal customs in the area, and was there when the murder took place of Frank Hawson and his hutkeeper Mr Biddle, an event which created considerable publicity in South Australia. Returning to Adelaide in 1846, he settled at Magill, taking business rooms in Adelaide and on Norwood Parade, and it was during this time that he published Timothy Short's Journal of Passing Events (1847).
In 1852 he left for the Victorian goldfields, returning in 1853, and editing the literary journal The Wanderer: A Monthly Periodical of Original Literature. This contained work published under his own name together with a number of anonymous works and pseudonymous works which may also have been by him. During this time he wrote his The Soul's Journey (1856) and the Circumstantial Narrative of the Wreck of the Steamship Admella (1859) and from 1857-1859 he was Secretary to the South Australia Institute Library. With the opening of the Yatala Labour Prison in 1861 Hailes was appointed Prison Storeman, a position he held until 1866 when he moved to Mount Gambier, working briefly again as an auctioneer before returning to Adelaide where he spent the rest of his life. He published his Personal Recollections of a Septuagenarian in 47 chapters in 1877-1879.
In addition to the well-known pseudonym 'Timothy Short' it is likely that Hailes was also the author behind the pseudonym 'Lancelot Yellowleaf' and was one of those who contributed to the column 'Echoes from the Bush' in The Register as 'Geoffry Crabthorn' (see Scrapbbooks compiled by Alan Horsnell, held in the Mortlock Library Archives of the State Library of South Australia).
