In "The Thinker," Anderson tells the story of Seth Richmond, a young man in Winesburg who has recently lost his father. In the aftermath of his passing, the Richmond family dynamic begins to deteriorate—Seth begins to act out, and Virginia, Seth's mother, finds herself unable to relate to her son. Anderson's depiction of the family dynamic, and particularly Virginia's vision of parenting as a cycle of small abuses, reads as a satire of the responsibilities of parenting and family dysfunction:
The truth was that the son thought with remarkable clearness and the mother did not. She expected from all people certain conventional reactions to life. A boy was your son, you scolded him and he trembled and looked at the floor. When you had scolded enough he wept and all was forgiven. After the weeping and when he had gone to bed, you crept into his room and kissed him.
Scolding and forgiving is not, in fact, all that parenting involves, but in the midst of the family crisis, Virginia cannot seem to escape this pattern of behavior. Seth, meanwhile, grows increasingly distant from his mother and even runs away for a short time. By emphasizing the overly simplistic way that Virginia approaches parenting, Anderson effectively satirizes this rather one-dimensional approach to raising children.
Like many characters in Winesburg, Ohio, Seth finds himself lost and alone in the formative years of his life. Anderson's portrayal of Seth's emotional separation from his family and peers furthers the exploration of alienation and grief that pervade the story collection.