Dobbie's documented early life centres on Brighton, a south-eastern suburb of Melbourne, Victoria, where he attended a boys' school from 1962 to 1971. Brighton's coastal location and its place within Melbourne's bayside suburbs formed the setting for his secondary education before he moved on to university study in the city.
Dobbie attended Brighton Grammar School from 1962 to 1971. The school was founded in 1882 by Dr George Henry Crowther, a University of Melbourne graduate, who opened it on 14 February 1882 with eight pupils. By 1907 the school had acquired additional land and opened a sports oval, establishing the foundations of the campus that later pupils used.
He then studied at Monash University, a public research university established in 1958 by an Act of the Victorian Parliament and named after the World War I general Sir John Monash. In its early years Monash offered undergraduate and postgraduate degrees in economics and law, and its law faculty was established in 1964. Dobbie's Monash qualifications comprised a Bachelor of Economics, completed between 1972 and 1974, and a Bachelor of Laws, completed between 1972 and 1976.
He was admitted to the bar in Victoria in 1978, and in 1982 he undertook a Diploma of Commercial Law at Monash. These qualifications prepared him for the commercial legal practice in Melbourne that formed the core of his career.
Dobbie's legal career in Victoria began with his admission to the bar in 1978. In 1987 he became a partner at Middletons Moore & Bevins in Melbourne, a firm whose history was traced back to the 1800s and which had been formed by a merger of several prominent practices. The Sydney and Melbourne offices of that firm operated together for about a decade before separating in 2001, when the Melbourne arm adopted the name Middletons.
Dobbie's practice centred on commercial litigation and dispute resolution, and he later described more than thirty years of experience in litigation. Within the firm's Dispute Resolution Group he worked on matters arising from the Longford gas explosion of 1998 at Esso's gas plant in Victoria's Gippsland region, including the Longford Royal Commission, the prosecution that followed, and a class action against Esso. He regarded the decade-long Longford work as the most significant matter of his career. His firm's litigation also included the Centro class action and proceedings arising from the gas explosion on Varanus Island off Western Australia.
In 2013 Middletons combined with K&L Gates, a multinational law firm headquartered in Pittsburgh and formed in 2007 through a merger of several American firms. The Australian combination brought Middletons' roughly 300 lawyers and its offices in Melbourne, Sydney, Perth and Brisbane into the global firm. Dobbie continued as a partner with K&L Gates in Melbourne until his retirement from the partnership in July 2023.
