A woman must decide between a career or love in this watercolor by the great American illustrator James Montgomery Flagg. At the time of this painting's creation, a woman's place in American society was at a crossroads. Congress had just endorsed the Nineteenth Amendment in 1920, giving women the right to vote. The idealized notion of the liberated woman of the 1920s, the "flapper," was just beginning to emerge. Flagg's compositions illustrates the new paths open to the modern woman, but also implies that women could not "have it all." Thus, it exists as an important piece of historic social commentary as well as a stunning work of American Illustration.

Born in Pelham Manor, New York, in 1877, Flagg was a true prodigy of American Illustration, selling his first design to the prestigious St. Nicholas Magazine at the young age of 12. He worked in a number of media throughout his career, though he is perhaps best remembered for his poster designs. His most famous work is undoubtedly his I Want YOU for U.S. Army poster, which he created along with 45 other patriotic posters in support of the war effort during World War I. His I Want YOU for U.S. Army design quickly became a household icon, and today it remains one of the most iconic images of the 20th century.

In addition to his work for the U.S. Army, he provided artwork to all of the major publications of his age, including Life, Collier's, Judge, Harper's Monthly, Cosmopolitan, the Saturday Evening Post and many more. He was also a successful painter of portraits, and in 1900 he had a portrait accepted at the Paris Salon, a remarkable achievement for an American painter.