Research has shown how dominant narratives about teenage mothers in high school situate them as a problem population because they are at risk of dropping out of school without promising employment opportunities. Illustrating the narratives of three Latina and Black women who graduated from high school as mothers, this qualitative study responds to these dominant narratives. Data were collected through three in-depth, semi-structured interviews with each participant and one focus group interview with all participants. Guided by work on narrative portraits, this study explores the participants' counternarratives with regard to success and failure in school. Findings show that participants expressed resolve and flexibility in the face of difficult and unforgiving life circumstances, and they articulated new ways of envisioning success that challenge traditional notions of achievement. By documenting the participants' counternarratives, this study makes a case for renegotiating the physical, socio-economic, and temporal boundaries around traditional notions of success. This study has implications for research and school-based practices in reconsidering how young mothers are supported in their efforts to succeed in high school and beyond.