Robert Indiana kept a series of illustrated journals during the late 1950s and 1960s, in which he discusses the development of his work.

In his journal page from December 31, 1959, Indiana discusses a work he calls October Painting (untraced). He includes a small sketch of the work, to the left of which he records "repaint blue." He also notes that the work is oil on canvas, and measures 30 x 18 inches, although a comment above the dimensions states "but a wee bit narrower in actuality. Alas."

Indiana describes the work as "a very seminal [painting]," noting that "it bears great debt to Youngermans [sic] more tortured forms, it possibly already repaid, or at least lose [sic] no great grace by this indebtedness; surely Jack is more graceful in his largese [sic] than Ellsworth [Kelly] who trembles lest anyone Hard Edge."

Indiana's journals also provide insight into his daily activities. Here he describes his New Year's Eve, which he spent with J. (his partner, fashion designer John Kloss), explaining that there were no parties for them so they saw the film Room at the Top at the Apollo and visited the Concord Bookshop, where he purchased B. H. Friedman's School of New York: Some Younger Artists, parting "with $1.95 of my money for Jasper Johns, Bob Rauschenberg, Alfred Leslie, Joan Mitchell, Larry Rivers, etc."

Because it was so cold and there were so few people at Times Square at ten they decided to return to Coenties Slip and see the New Year in quietly in the loft over hot cider. Midnight was marked by a great blast from the tugboats at the empty pier below, and the sight of "Ellsworth, running with his arms and legs out like pinwheels went spinning down the Slip with Orange [Kelly's dog] at his heels."