Fleishman Is in Trouble reverses normative gender roles within the family. In many novels, films, and stories, the father works long hours, is professionally ambitious, and as a result, becomes distant from his children. In Fleishman Is in Trouble, Rachel, the mother, is the ambitious one, and she becomes distanced from her children’s emotional lives. Toby, the father, takes on more child-rearing duties and is more present for his children. Though he is a doctor, he arranges his work hours so that he can be home by dinner time.

Although the husband’s ambition drives a wedge into marriage in most stories, in Fleishman, the wife’s ambition becomes a sore point in the Fleishmans’ relationship. In Part 1, Toby rails against Rachel for prioritizing her social calendar and professional life over her role as a mother: 

She’d miraculously become available when the Rothbergs or the Leffers or the Hertzes invited them over for a Friday night dinner. But otherwise, she’d call and say that she “needed” to stay at work because she “needed” to get things done, knowing […] that it was actually her resistance to spending time with her children and to some notion of a traditional role as a mother that made her want to work that much (56).