Ted Geisel moved from New York to La Jolla in 1948. Along with his “La Jolla Bird Woman” series, "Gosh! Do I look as old as all that!" exemplifies his interest in depicting the attitudes of the housewives in the affluent coastal area. Geisel worked from home and was well-acquainted with many of the women in the area.

The contrast between "Gosh!..." and "Self-Portrait of the Artist as a Young Man Shaving" demonstrates the difference in attitudes among the generations. There is also a contrast between the sexes, but even Geisel felt age keenly, as shown by his "Self-Portrait of the Artist Worrying about his next Book." Geisel portrays himself as a wisened older gentleman, feeling the strain of the years.