Initially employed as a proofreader, Pickering was able to gain the attention of John Allan, the editor of The Canberra Times.
[1] It was at this time his first book of cartoons, The Hansard Papers, written by Reuters Economic Services Canberra correspondent Michael Guy and illustrated by Pickering was published and went to No.
[1][6] For the next thirty years Pickering focused on other pursuits, such as training racehorses and growing tomatoes, but in 2011 he returned to political cartooning.
[10] In 2010, Pickering was made an undischarged bankrupt on petition from the father of his former de facto, but in reply denied he owed any money and stated his "only asset is a $250 set of golf clubs".
[11][12] Pickering acknowledged he helped establish Cohen Strachan Investments, a betting software company which went into bankruptcy in 2010 with millions of dollars lost by gamblers.
[11][13][14][15] In November 2015, Queensland Fraud Squad detectives reopened the investigation into Pickering's involvement in Cohen Strachan Investments.
[16] The Supreme Court of Queensland found that Pickering derived "significant financial benefits" from Hamlyn Crest, the Australian distributor of the betting software, and that his denial of involvement in the management of the company was "thoroughly implausible".