Pickering started his career as a journalist but wrote his first novel, Wild About Harry, after an assignment to Paraguay to find the war criminal Josef Mengele.
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Pickering was for a while under siege in the Nicaraguan town of Bluefields, where he helped former Baader-Meinhof printer, novelist and playwright, Peter-Paul Zahl, build a Bertolt Brecht youth theatre after his first was destroyed in the invasion of Grenada.
He carried out mural decorations for the Royal Academy Refreshment Room in 1903, St Mark's, North Audley Street, two large paintings in Nottingham General Hospital and Church of SS Peter and Paul, Pickering, Yorkshire.