Thomas Smith’s Self-Portrait (ca. 1680) is the earliest known self-portrait produced in New England and the only painting extant from this period identified with a specific artist. Smith is commonly assumed to have composed the eight-line poem “Why Why Should I the World Be Minding” that appears in the portrait. In fact, these verses are the English translator Josuah Sylvester’s version of a French octonaire that was written by the Huguenot minister and author Simon Goulart and set to music by Paschal de L’Estocart in the early 1580s. This discovery casts fresh light on how the arrangement of elements in the portrait was consistent with the aesthetic values of early American Puritan culture that the painting is taken to embody. Specifically, it calls attention to how the poem functions like a “motto” (the word used when the English poem was first printed in Sylvester’s Devine Weekes, and Workes) that illuminates the spiritual significance of the portrait’s emblematic features.