This article presents data from a 10-month case study of a critical literacy writing group for parenting and pregnant young adults. The author focuses on the efficacy of the program to foster the critical literacy skills of two participants. Drawing on field notes and written artifacts and using case study and discourse analysis, the author suggests that, although they redefined their figured identities in the program, the two women’s ability to take action in their lives—their selves-in-practice—was contingent on other factors beyond the influence of the Program, such as familial and significant others’ influences, which were definitive and integral to who the participants were. Thus, how the participants figured or positioned themselves inside and outside of the program was fluid and sometimes contradictory and greatly influenced by the symmetry between competing figured worlds, in which they participated and the strategic and practical gender needs that informed their positional identities in their day-to-day lives.