[2] It was during one winter between 1907 and 1912 that both this room and his office (where Frances Shute, his secretary, would sometimes stay late typing drafts of his first two novels) served as the settings in which Windy McPherson's Sons was composed.

[5] The beginning section of the novel is inspired by his youth, the second "...combined the ways he had tried to make money in Chicago and Ohio..." and the marriage between Sam and Sue resembles the one between Sherwood and Cornelia.

[8][9] In addition to the personal connections between Windy McPherson's Son and the author's life made by biographers and critics, the influence of other writers is also seen in the book.

McPherson starts out as an ambitious newsboy in Caxton, Iowa, with drunkard of a father who constantly embarrasses him.

Eventually, after his mother's death and an episode with a middle-aged schoolteacher, McPherson leaves Caxton for Chicago.