Black and Latinx adolescent boys from economically stratified communities face pervasive societal inequities and, therefore, deserve more responsive school supports to determine and actualize postsecondary pathways. For insights into how such students conceptualize their futures and their school's role in facilitating this process, this ethnographic study investigated one urban school's college-going culture and its impact on shaping what the author calls participants' postsecondary future selves. This theoretical approach encompasses three domains: college (i.e., postsecondary education), career (i.e., post-college employment trajectory), and condition (i.e., expected financial stability, relational and familial prospects, future living arrangements, happiness, and joy). Implications suggest that college-going school practitioners widen supports so students can imagine and envision how college ambitions align with career and condition goals.