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Sheldon began illustrating when she was nine years old, contributing to her mother's book, Alice in Elephantland, a children's book about the family's second trip to Africa. Sheldon appeared in it as herself. One of the illustrations was a depiction of herself holding a gun, an image she drew after her father told her she could not have one on their expedition. Sheldon later had an exhibit of her drawings of Africa at the Chicago Gallery, arranged by her parents.

Although Sheldon illustrated several of her mother's books, she only sold one illustration during her lifetime. In 1931, during her first year at Andrebrook, a small New York boarding school, she sold an illustration to The New Yorker, with help from Harold Ober, a New York agent who worked with her mother. The illustration, of a horse rearing and throwing off its rider, sold for ten dollars.

In 1936, Sheldon participated in a group show at the Art Institute of Chicago, featuring new American work. She had connections to the art institute through her family, influential family friends from Chicago the McCormicks, and Randall Davey, her step father at the time and painter. This was considered an important step forward for her painting career. It was during this time that she also took private art lessons from John Sloan an old friend of Randall Davey. Sheldon disliked prudery in painting. While examining an anatomy book for  an art class, she noticed that the genitals were blurred, so she restored the genitals of the figures with a pencil.

In 1939 , Sheldon’s nude self portrait titled Portrait in the Country was accepted for the "All-American" biennial show at the Corcoran Gallery in Washington D.C., where it was displayed for six weeks. While these two shows were considered  big breaks, Alice disparaged these accomplishments, saying that “only second rate painters sold" and she preferred to keep her works at home.

By 1940, Sheldon felt she had mastered all the techniques she needed and was ready to choose her subject matter. However,  she began to doubt  whether she should paint. She kept working at her painting techniques, fascinated with the questions of form and read books on aesthetics in order to know what scientifically made a painting "good."

Sheldon stopped painting in 1941. In need of a way to support herself, her parents helped her find a job as an art critic for the Chicago Sun after it launched in 1941. Newly divorced, she  started going by the name Alice Bradley Davey as a journalist, a  job she held until she enlisted in the WAAC, later known as the WAC, in 1942.

Sheldon's work as a professional painter was fairly short, only lasting from 1936 to 1942. While she was considered a talented painter and was able to sell her work she saw it as a job her parents wanted her to have and she did not feel independent doing it. She also believed that artists who made work to sell it were not pure artists, preferring to keep her own works at home rather than commodify them.

Her work as an illustrator was a more enduring endeavor. The first professional illustrations she did were for children’s books written by her mother, Alice in Jungleland and Alice in Elephantland. She did the illustrations for these books when she was nine years old. The only illustration she ever sold was of a horse rearing up and throwing off its rider, which she sold in 1931 to the New Yorker. In 1975, she contributed drawings, along with letters and a poem, to a feminist fanzine, though this was done under her pen name Raccoona Sheldon. She also included doodles in the letters and postcards she sent to her friends under all her various personae.