During World War II, when Thinking Ahead was executed, Kuniyoshi's paintings attained their greatest poignancy. The melancholy mood and gloomy atmosphere of this work is defined by the woman's contemplative countenance, which dominates the canvas. Her solemn expression is accentuated by her distracted, lowered eyes, tilted head, and expressive, attenuated fingers, which rest upon her forehead and temple. Additionally, the sweeping strokes of cold gray and dull rust in the woman’s clothing and desolate surroundings emphasize the somber setting. The image of a woman's draped head set against a backdrop of a threatening sky or deserted landscape recurs in Kuniyoshi's work at the time.
Thinking Ahead reflects, in its fully realized forms and atmospheric landscape, the increased influence on Kuniyoshi of naturalist tendencies that characterized much of American art in the 1930s and early 1940s. However, rather than merely replicating appearances in his paintings, he generalized and altered reality, sometimes adding surrealist elements in order to express his personal vision. In Thinking Ahead, an oriental quality is retained in the sketchy lines, which dissolve the figure into its surroundings and create rhythmic unity through sensitively harmonized gray and brown brushstrokes.
Kuniyoshi's work of the 1930s and 1940s was characterized by images of beautiful women posed in various states of contemplation. In the late 1930s, as World War II was approaching, Kuniyoshi's women became increasingly glum and depressed. His works during the War could often be gloomy and pessimistic, revealing the Japanese expatriate’s precarious situation in the United States at this time, as well as his concern for the human suffering brought about by the War.