Prior research has discussed high school counselors’ role in students’ experience, but counselors’ understandings of their work and of students has received little commentary. We interviewed counselors in a high-poverty, low-performing urban school district in which two structural elements shape how counselors make sense of their work. First, counselor “success” is contingent on convincing students to act in (what schools see as) students’ own best interest, and many students do not do so. Second, resource constraints severely limit planned one-on-one counseling. We find that counselors see students as both victims of crushing circumstances and as agents actively undermining their own opportunities, as holding ambitions misaligned with performance and as vulnerable to despair. Counselors’ strategies follow from these conceptions: building self-efficacy, emphasizing the importance of goals, and nudging plans toward realizability while maintaining hope. We discuss how counselors cope with the rarity with which they experience professional “success,” given student outcomes.