We investigate how context might influence adolescent boys' and girls' ambition and the impact of gender role conformity and social status. Adolescent participants (N = 270) reported their ambition in one of three experimentally manipulated contexts: future education, future work, or a control. Boys experienced a significant negative drop in ambition in a future education context versus control. There was no difference for girls. Gender role conformity moderated the effects for boys such that the more conform, the less ambitious in an educational context. There was no moderating effect for girls. Social status had no moderating effect. Explanations are discussed, including how negative academic gender role stereotypes may affect boys' ambition and the importance of addressing boys' cultures at school.