Flannery O'Connor's first published works were her cartoons published in the Peabody Palladium, the student newspaper at O'Connor's high school. According to the Palladium, by the end of 1941, O'Connor had written and illustrated three books about geese: Mistaken Identity, Elmo, and Gertrude, which O'Connor was unable to publish. The same article mentions Mary Flannery O'Connor's school notebook, which was painted with oils and covered with cellophane. Around this same time O'Connor was also designing handmade lapel pins which were for sale at a local store in Milledgeville
O'Connor's career as a cartoonist continued at Georgia State College for Women when her cartoons began appearing as early as October 1942 in the college newspaper, The Colonnade. O'Connor's cartoons depict humorous views of life on campus including, school performances, social activities, studying and life on campus with the WAVES.
During her years at GSCW her cartoons appeared in almost every publication the college produced including the alumni magazine, the literary magazine, and on a weekly basis in the newspaper, the Colonnade. In 1944 O'Connor was appointed Art Editor of the college yearbook, the Spectrum, and designed numerous cartoons for the 1944-1945 yearbook, including the inside covers depicting campus scenes. In 1944 O'Connor also submitted cartoons to The New Yorker, but the magazine was not interested in publishing them. (CW 1240)
Many of O'Connor's published cartoons were linoleum-block prints. Linoleum-block printing involves cutting or etching an image on to a linoleum sheet. In O'Connor's case, she attached the linoleum to a piece of wood, applied a solid color of ink to the linoleum cutting, and printed the image on to a piece of paper. The image was then printed in black and white in the final publication.
O'Connor's interest in creating cartoons continued as she left home in 1945 to pursue a graduate degree in writing at The University of Iowa. Among O'Connor's first courses at The University of Iowa were two courses in advanced drawing. She hoped to be able to support her writing by selling cartoons to national publications. O'Connor, however, was unable to sell any of her cartoons, at which time she began devoting all of her energy to writing.