Upon her return to Virginia after finishing her first year of studies at the Art Students League, Georgia realized the economic desperation of her family. Her father’s repeated business failures left him morose and bankrupt, and her mother, having fallen ill with tuberculosis, spent most of her time in bed. Even though Georgia’s sisters had not completed high school, her family had to withdraw them and direct the remaining funds to finance their other son Alexius’ education. Because there was not enough money for Georgia to continue her education, she decided to find a job.

In 1908 O’Keeffe returned to Chicago to work as a commercial artist, drawing lace and embroidery for advertisements. This high-pressure career was demanding, as newspapers had daily deadlines and competition between artists was fierce. Though Georgia, with her ability to draw quickly, was a successful contender, the work was largely meaningless to her.

After two years of working in this commercial setting, Georgia contracted the measles. She could no longer continue her work after the disease began to affect her eyesight. In 1909 she decided to move back to Virginia, where she worked at home, helping her mother with the boarders. Acting on advice from her doctors, Ida decided to move to Charlottesville, hoping that a different environment would ameliorate her bronchial problems. Once her mother was established at her new home and boarding house, Georgia moved to join her with the rest of her siblings. During this time Georgia also had the opportunity to study at a local college.

At the advice of her sisters, O’Keeffe started to attend Alon Bement’s art classes. She learned about the artistic theories of Arthur Wesley Dow, who had been influenced by Oriental art, and the sense of completion in a composition. Moreover, Bement supported crafts as art, and taught his students the appreciation of design and the methods used to create design. He insisted that art could not replicate nature, but that beautiful art could result from building an elegant design based on nature. Rather than emphasize the need to create exact representations of nature, he stressed the assets of a beautiful and complete composition. This thinking made Bement’s ideas revolutionary in contrast to existing methods of teaching art, which rewarded students who replicated nature identically.

Dow’s method emphasized more freedom in art using colors and lines than Georgia had previously encountered. Recognizing Georgia’s talents and interest, Bement offered her a summer teaching position, but encouraged her to study drawing with Dow in New York. At the time, however, Georgia could not commit herself to pursuing an education, and decided to gain experience teaching so that she could qualify to teach during the following summer. She had long desired to travel to the American west, and when a former classmate from Chatham informed her that a teaching position was open in Texas, she took up the opportunity. Between 1912 and 1914 O’Keeffe served as art supervisor at a school in Amarillo, Texas. During the summers she taught drawing in Virginia, where her family’s economic situation had improved somewhat when Francis established a creamery.

Georgia was attracted to the environment and wildness of Amarillo, which was at that time still considered a frontier town. The extreme and unregulated forces of nature, the strong winds and flooding streams excited her. Moreover, the people of the area, accustomed to the physical environment, stood in stark contrast to the culture she had left behind in the urban areas of the east. Although O’Keeffe had time to experience life in Amarillo, she also worked tirelessly as the art supervisor. Her position necessitated creativity, as Amarillo was not a picturesque town. She therefore taught students to appreciate their surroundings and to see beauty around them. When she encouraged the students to draw what they loved, one student brought his pony to class, which Georgia lifted up on the teacher’s desk so that everyone could see it and draw it. Her indifference to convention inspired students and other teachers, but it did bring her into conflict with authorities who insisted on adhering to established lesson plans and art books. O’Keeffe, in contrast, insisted that art education be based on self-expression rather than conventional mimicry. She felt that duplicating reputed paintings and patterns was useless, especially for students who had no first-hand experience with the environments and natural settings of the paintings they copied. Eventually, Georgia succeeded in convincing her superiors in following her methods, but she continued to have trouble working exactly in the manner that she wanted.