For many years, Page worked at a series of jobs in an attempt to support his family. In the early 1870s, he helped his mother cook for Wisconsin Central Railway workers. Additionally, he worked as a railway dispatcher and clerked in a general store. In 1876-1877, he worked as a lumberjack and logger. In 1879, he became a policeman in Ashland, Wisconsin. In the following two years, he became chief of police for Tower, Minnesota, and then went to work for the Pinkerton National Detective Agency.