As a telegrapher, Brinkley went to New York City to work for Western Union, after which he moved to New Jersey to work at one, then another, railway company. In late 1906, he returned home to Aunt Sally after hearing that she was unwell. She died on December 25, 1906. Afterward, he was comforted by Sally Wike, age 22 and one year older than Brinkley. They married on January 27, 1907, in Sylva, North Carolina. They traveled around posing as Quaker doctors, giving rural towns a medicine show where they hawked a patent medicine. Brinkley's next move was to Knoxville, Tennessee, where he played right-hand man, helping hawk virility "tonics" with a man named Dr. Burke.