Given that many urban students exclude Science, Technology, Engineering, and Mathematics careers from their career choices, the present study focuses on urban high school students and adopts the social-cultural approach to understand the following questions: how do students envision their careers? What are the experiences that shape students' self-reflections? And how do students' self-reflections influence the way they envision their future careers? Five students were interviewed and data were coded in two ways: by topic domains and confidence levels. The research findings indicate that: first, a lack of information about future careers limits students from developing effective strategic plans; second, students' perceived ability to handle situations of potential barriers and communications with their parents might contribute to their certainty about and confidence in future careers.