In the last thirty years of his life, James worked a variety of jobs, including as a shoe salesman and then as a burlesque theater ticket taker in St. Louis. One of the theater's spins to attract patrons was their use of the phrase "Come get your ticket punched by the legendary Frank James." He also served as an AT&T telegraph operator in St. Joseph, Missouri. James took up the lecture circuit, while residing in Sherman, Texas. In 1902, former Missourian Sam Hildreth, a leading thoroughbred horse trainer and owner, hired James as the betting commissioner at the Fair Grounds Race Track in New Orleans. He returned to the North Texas area where he was a shoe salesman at Sanger Brothers in Dallas. The "Tacoma Times" reported in July, 1914 that he was picking berries at a local ranch there in Washington state and planned to buy a farm nearby. He was also part of a Chicago investment group which purchased the Fletcher Terrell's Buckskin Bill's Wild West Show, third in size after the Buffalo Bill and Pawnee Bill shows.