At Harvard, he majored in engineering sciences, but took the majority of his electives as writing courses. He published his first story, "The Greatest Thing in the World," at the age of 18, winning Story magazine's college contest in 1941.

Early in his career, Mailer typed his own works and handled his correspondence with the help of his sister, Barbara. After the publication of The Deer Park in 1955, he began to rely on hired typists and secretaries to assist with his growing output of works and letters. Among the women who worked for Mailer over the years, Anne Barry, Madeline Belkin, Suzanne Nye, Sandra Charlebois Smith, Carolyn Mason, and Molly Cook particularly influenced the organization and arrangement of his records.