Commissioned by Princess Holstein-Beck of Russia, this self-portrait by Kauffman is both vibrant and revealing. It shows the two possible career paths that were available to her as a young woman - music and painting. However, in the eighteenth century, female singers were often viewed as promiscuous, so Kauffman sought advice from a priest who recommended painting as the more virtuous option.

The allegorical nature of the painting invites comparisons with Annibale Carraci's Hercules at the Crossroads Between Virtue and Vice, a popular image of the time. Despite criticism that her paintings lacked the virility and manly strength typical of history paintings, Kauffman's decision to create a picture similar to a revered work demonstrates her astute understanding of the art market.

This self-portrait is unprecedented in its depiction of a female artist making important decisions for herself. Unlike her male contemporaries, who typically portrayed women as weak and subservient, Kauffman's paintings feature strong and empowered female protagonists. Additionally, the popularity of "choice" paintings at the time suggests an early interest in exploring individuality and psychology.