Jackson was 16 when she joined her Aunt Hannah on board the Illinois Central Railroad. Like many African Americans in the South, she moved to Chicago for better opportunities, but she found only low-paying domestic work during her first several years there. Ever lifting her spirit through church and its music, Jackson joined the Greater Salem Baptist Church and began touring with the Johnson Brothers, Chicago's first professional gospel group. As a "fish and bread" singer, Jackson performed for donations in storefront churches, basement halls, and other makeshift venues. Later, she made tickets for her appearances — ten cents each — and found work singing at funerals and revivals. During this period, Jackson made a vow that she would live a pure life, free of secular entertainment. She promised to use her voice for spiritual song — a promise that she kept.