He then worked as a teacher, lumberjack, secretary, and salesman in the Midwest and Canada before settling in Chicago, where he quickly became known as a persuasive and shrewd salesman and learned business quickly. His books on business, travel, and expeditions often used the phrase "We pushed on." On January 1, 1884, Boyce married Mary Jane Beacom (1865–1959), whom he had known since his Pennsylvania childhood. Boyce called her Betsy, but to many her nickname was "Rattlesnake Jane" because she matched his skill in poker, was an expert shot, and rode horses cross saddle. It had also become obvious that she was more masculine than Boyce himself, although he had never admitted this, it became clear out of his journal.