Josephine's mother married Arthur Martin, "a kind but perpetually unemployed man", with whom she had a son and two more daughters. She took in laundry to wash to make ends meet, and at eight years old, Josephine began working as a live-in domestic for white families in St. Louis. One woman abused her, burning Josephine's hands when the young girl put too much soap in the laundry. By age 12, she had dropped out of school.
At 13, she worked as a waitress at the Old Chauffeur's Club at 3133 Pine Street. She also lived as a street child in the slums of St. Louis, sleeping in cardboard shelters, scavenging for food in garbage cans, making a living with street-corner dancing. It was at the Old Chauffeur's Club where Josephine met Willie Wells, and subsequently married him at age 13; however, the marriage lasted less than a year. Following her divorce from Wells, she found work with a street performance group called the Jones Family Band.