This paper reflects upon the nature of a target-setting and mentoring scheme in an 11-16 school in England, through a series of retrospective interviews with students who continued into further education. It considers the extent to which the initiative impacted both upon students' formal academic achievement at 16+ and upon the subsequent longer-term aspirations of these students. Interviews with students who achieved considerable "value-added" in their GCSE examinations suggested that the impact of mentoring was strongest amongst those students who came from homes where there was less expectation of them participating in further and higher education, and that this effect was not differentiated according to gender. The paper suggests that longer-term transformation of students' aspirations, and the challenging of gendered course and career stereotypes, will only be achieved if schools adopt a more holistic and proactive approach to careers education and to widening participation for their students, and that the absence of such proactivity will limit the longer-term gains initiated by successful mentoring activities. (Contains 1 figure, 1 table, and 6 notes.)