Throughout the 1970s and 1980s, DeArmond wrote several historical columns for southeast Alaska publications; these included Days of Yore, Gastineau Bygones, and News of the Gold Camp.
He worked in a salmon cannery in the summer of 1930, and later received a reporting job for the Stroller's Weekly in Juneau.
He worked for the Ketchikan Daily News, the Juneau Empire and other publications in covering the Alaska Territorial Legislature.
Over 700 of his columns were put in the online Digital Bob project, sponsored by the Juneau-Douglas City Museum, beginning in 2004.
[7] DeArmond worked for territorial governor B. Frank Heintzleman in the 1950s and lived in Juneau during this time.