In 1889 Stedman decided that he wanted to be a lawyer. He approached the dean of the Northwestern University School of Law and told him of his desires, admitting that he had had only three years of formal education. After grilling the youth for an hour to determine Stedman's level of reading capability and intelligence, the dean relented and admitted Stedman to the university. Stedman continued to work as a janitor during the day and attended university lectures in the evening. He was ultimately admitted to the Illinois State Bar Association in 1891.