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Criminological studies have examined women’s involvement in street-level prostitution, but very few have examined who they aspired to be in childhood and their perceived barriers to attaining their professional goals. This qualitative study analyzes 34 interviews with women who completed a prostitution diversion program (PDP) in a Southwestern state, between October 2024 and February 2026. During the interviews, women were asked about their childhood career aspirations, whether they still hoped to achieve them, and what barriers they faced if those goals were not realized. Findings from the study emphasize how structural and interpersonal barriers, such as exploitation, financial instability, trauma, and criminal legal involvement, derailed women’s pursuits of their professional goals. Findings have implications for diversion programs by highlighting the importance of acknowledging women’s identities, past, and future-oriented goals rather than focusing solely on their experiences in prostitution.