This article juxtaposes The Good Wife’s (TGW) representation of Alicia Florrick’s experience as a professional woman and a mother, against interview accounts of middle-class women who left successful careers after having children. I show that TGW furnishes a compelling fantasy based on (1) the valorization of combining motherhood with competitive, long-hours high-powered waged work as the basis for a woman’s value and liberation, and (2) an emphasis on women’s professional performance and satisfaction as depending largely on their individual self-confidence and ability to "lean in," while marginalizing the impact of structural issues on women’s success and workplace equality. This fantasy fails to correspond to women’s lived experience, but shapes their sense of self in painful ways. The TGW fantasy thus involves a relation of "cruel optimism": it attracts women to desire it while impeding them from tackling the structural issues that are obstructing realization of their desire.