Richard James Sullivan (later known as O'Sullivan) was born at Kilkenny, County Kilkenny, Ireland, and baptised there on 10 January 1826. He was the son of Richard Sullivan, a merchant, and his first wife, Catherine Hackett. In 1832, Sullivan's father became the first Catholic since the reign of James II to represent Kilkenny in Parliament. He resigned his seat in 1836, and subsequently served Kilkenny as mayor and high sherriff. Little is known of Richard's early life, although his mother died in 1828.
He married Anastatia Mary Montgomery on 26 January 1853 in London, England, and they emigrated to Auckland, New Zealand, in 1857. O'Sullivan was initially employed as the founding teacher of St Peter's, a Catholic school in central Auckland with a roll of 37 boys. He became the publisher of the Southern Cross newspaper, and shortly afterwards the clerk and librarian of the Auckland Provincial Council.
In 1869 the council passed the Common Schools Act establishing non-denominational schools in the province. O'Sullivan became secretary to the Central Board of Education, also established by the act, and the board's school inspector with an annual salary of £400. His appointment was criticised on the grounds that he held too many positions and was not 'a practical teacher'. His duties were to visit and inspect all schools in the province at least once in every year, report on any relevant matters, witness the examination of scholars by their teachers, assist in the examinations, investigate all complaints and present an annual report.
O'Sullivan was vigorous in his inspection duties, and his records show his rapid movement around the large and mainly poorly roaded district. He flitted from place to place, spending a day at each school; inexperienced teachers would have preferred him to remain longer and to give more practical assistance. His reports pointed out to the Board any errors or misdemeanours: some schools allowed their rooms to be used for dancing and other purposes, while some teachers failed to comply with regulations concerning the calling of the attendance roll and school cleaning.
Education became the responsibility of central government in 1877, and O'Sullivan continued to serve as inspector for the new Auckland Education Board. His reports reflected his conviction about the need for hard work and consistent application. He was unrelentingly critical of the poor teaching he found and stressed the need for rigorous discipline. While not an advocate of corporal punishment, he supported good behaviour and told teachers that order was kept 'not by the voice, nor by the stick, but by the eye. Of course, it must be by the seeing eye, not that which glares with no speculation in it.' He also felt that school prize-givings left children 'puffed up with injudicious praise'; they should instead be 'relegated to their proper and natural position of insignificance.' His Instructions for the guidance of teachers (1880, 1889) was well regarded.
Towards the end of his career, O'Sullivan became increasingly resentful of the board's attempt to control matters that he felt fell within his own domain, and of their failure to seek his advice on matters of which they had little direct knowledge. He retired in March 1888, having made a major contribution to the organisation of education in Auckland. If, as a Catholic, he was at times subjected to petty persecutions, he never complained of them. He died at his home in Three Kings, Auckland, on 5 November 1889, survived by Anastatia and six children.