Robert Indiana kept a series of illustrated journals during the late 1950s and 1960s, in which he discusses the development of his work as well as his daily life on Coenties Slip.

This journal page covers August 31–September 1, 1960. In his entry for August 31, 1960, Indiana does not discuss any works, recording only that:

"A white freighter glided through the topmost leaves of the sycamores of Jeanette [sic] [Park], just as I was at the front dormer. A provoking reminder [that] [the] summer has passed swiftly by, smoothly (mercifully smoothly), but a final season, a near final sight, surely, on the Slip."

His entry for September 1, 1960, includes a sketch of the herm Hole. Indiana notes that he painted the word "hole" in raw sienna, stenciled, and that it references Samuel Beckett's novel Molloy. A note which Indiana added at a later date records that the work was in his studio in 1962.