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Friedrich experimented with printmaking early on as a student of Carl Otto Czeschka in Hamburg, between 1913–18. He became a member of the Expressionist group “Kräfte” in Hamburg (with Kinner von Dresler, Paul Adolf Seehaus, and Andreas and Peter Luksch). One of his artist friends was Johannes Wüsten, who portrayed him and dedicated his novel “Ywon – A Story of a Double Life” to him. His images, which are strongly reminiscent of Expressionism, range between realistic depictions of nature and bizarre fantasy. Most of his prints are considered rare, due to the small editions. In his etchings he tended to experiment, pushing technical boundaries. He was inspired by Hercules (Pieterszoon) Segers (1589–1638) and the history of intaglio printing, for which he published the book Handlung und Gestalt des Kupferstiches und der Radierung, Fredebeul & Koenen, Essen 1931.