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Aspirations are strong predictors of students’ trajectories, and understanding how youth develop and achieve goals is crucial to supporting their future success. Guided by ethical educational research frameworks and evidence-based counseling practices, this paper foregrounds “motivational interviewing” (MI) as an innovative contribution to qualitative methodology, in the context of a broader study on youths’ aspirations. Data were collected via 50 interviews with five first-generation, low-income, Mexican-American high school seniors over one year. Semi-structured interviews followed an MI approach, which cultivated space for students’ emergent thinking and sensemaking about how current experiences affected their future pathways. Findings demonstrate how MI enabled co-construction of reflective, affirming, imaginative dialogue opportunities. This study offers implications for qualitative research and possibilities for employing person-centered methods.