Bolles was managing editor of the "Buffalo Enquirer" in 1902 and 1903; superintendent of graphic arts of the St. Louis Exposition from 1903 to 1905; and director of publicity of the Jamestown Exposition in 1907. He was engaged as a special writer and also in private business, including the "brokerage" business, in Atlanta, Georgia from 1907 to 1919. In 1920, he moved to Janesville, Wisconsin, as editor of the "Janesville Gazette" and remained until 1939.