In 1914 Georgia was drawn back to New York City to attend Columbia Teachers College and to study with Dow. She had benefited from her experience in Amarillo, but she did not want to return to struggle again with higher-ups in her position as art supervisor. O’Keeffe carefully planned her finances so that she would be able to study again. At Teacher’s College, she continued to do well in creative courses, but her grades in academic subjects such as English were poor.

Now twenty-seven years old, Georgia was wiser, more experienced and serious, and painting became her first priority. She was affected by the New York environment, which had changed significantly since she had been there in 1908. New ideas in art were more widely discussed, and political activism–exemplified by Max Eastman’s radical magazine, The Masses–thrived along with artistic innovation and creativity. Georgia attended Charles Martin’s course at the Art Students League, where she met her future friends Anita Pollitzer and Dorothy True. Pollitzer, who was involved in the women’s suffrage movement, also interacted with Alfred Stieglitz and frequented his gallery, 291.

From 1913 to 1916, O’Keeffe spent every summer working as Bement’s assistant in Virginia. He acted as her mentor, exposing her to important ideas such as those in Wassily Kandinsky’s On the Spiritual in Art, stressing the importance of inner emotions. During the summer of 1915, O’Keeffe continued to paint, socialize, and maintain contact with political debate by reading The Masses while working in Virginia. She began to see Arthur MacMahon, a professor from New York, who exposed her to more liberal political ideas, especially about the position of women.

In 1915 she continued her teaching career at Columbia College in South Carolina. Once again, her financial situation did not allow her to continue with her education, and she had to accept an offer to teach to earn money. O’Keeffe soon felt stifled in the old Confederate city of Columbia, but she continued to create artwork. Building upon her artistic influences, she began to produce charcoal drawings according to her own feelings, acknowledging what felt natural to her without adhering to accepted conventions. She had intense feelings for MacMahon, who had visited her during Thanksgiving, and she attempted to confront her sensual feelings by drawing. This initial digression suited her artistic aspirations. In 1916, when Anita Pollitzer introduced Alfred Stieglitz to O’Keeffe’s work, he immediately accepted to show it in his 291 gallery. When Georgia received news of Stieglitz’s response, she was surprised but pleased. She wrote to Pollitzer:

Georgia was offered a position to teach at West Texas State Normal College in the fall of 1916. However, this position depended upon her attendance of Arthur Dow’s spring course at Teacher’s College. Longing for the flat landscapes of Texas, Georgia committed to accept the position, quit her current job, and moved back to New York to attend classes despite her limited financial resources. While studying that semester, Georgia received the disappointing news of the death of her mother, an event that splintered her family.

Stieglitz did show O’Keeffe’s charcoals in an exhibit with other artwork, although he did it without consulting her. Georgia rushed to 291 after one of her colleagues mistakenly informed her that paintings by "Virginia O’Keeffe" were on display. O’Keeffe, realizing that it was probably her artwork, went to verify her suspicion. After confronting Stieglitz, she agreed to allow her drawings to hang in the gallery.

The town of Canyon, Texas, was smaller than Amarillo, but Georgia kept to herself, to her job, but most of all to her artwork. The exhilarating desert sky excited Georgia, especially when it was penetrated with the lightning strikes or the stars that illuminated the night. Inspired by the steep slopes and the colors of Palo Duro Canyon, she spent much time painting watercolors which were later displayed at her first solo exhibition at 291, between April 3 and May 14, 1917. O’Keeffe continued her correspondence with Pollitzer and Stieglitz, sending them her artwork. One painting, Blue Lines (1916), was hanging in Stieglitz’s gallery in December of 1916 when Anita went to visit him. This painting, which represented the canyon, demonstrated that O’Keeffe had mastered the line using nature as her guide. Georgia soon became ill with the flu, resigned from her job, and, at the advice of Stieglitz, returned to New York in June of 1918.