He worked as a solicitor in the inner Sydney suburb of Kings Cross and then served as a barrister specialising in family law in the Northern Territory and New South Wales.
He also contributed to church and public discourses concerning right-to-life issues and the proposed Australian Bill of Rights, which was debated and defeated during Bob Hawke's term as Prime Minister of Australia.
He also became involved with the Sports and Leisure ministry in Australia and eventually co-wrote two books recounting the spiritual conversions of Australian and International sports-stars such as Nick Farr-Jones, Wes Hall and Bernhard Langer.
During 1991 he co-founded with Philip Johnson a para-church ministry known as The Community of Hope, which began developing exhibitor's booths as a form of dialogue and witness in alternative spiritual festivals in Sydney.
[6] Clifford served as President of the New South Wales Council of Churches throughout the late 1990s, during which time he oversaw an apology to the state's indigenous population for harm caused by the activities of early missionaries,[7] vocally supported gun control in the wake of the Port Arthur massacre and resisted a push from the hotel industry to put poker machines in hotels across the state.
In early 1999 Clifford became a Sunday evening radio announcer, appointed to fill a talkback vacancy on Sydney easy listening station 2CH.
[9] In 2003 Clifford attempted to make a move into politics, nominating as a Christian Democratic Party candidate for the New South Wales Legislative Council at the 2003 state election.
[11] Clifford looked set to receive a second chance at a political career in late 2004, when Nile resigned from the Legislative Council to run for a seat in the Australian Senate.
As the party's highest unelected candidate at the previous state election, he was the obvious choice to replace Nile in the Legislative Council and was ultimately nominated to fill the casual vacancy.
[citation needed] In January 2001 the Australian Commonwealth Government awarded him the Centenary Medal in recognition of his ministry, and in June 2010 he was made a Member of the Order of Australia.