Chapter 8 explored how organizational social mobility programmes have a limited effect including as young people from working class backgrounds feel stigmatized and indelibly marked. Chapter 9 moves on to consider in further detail how they respond, to underline that while these young people have agency, it is exercised within considerable constraints. Remaining with legitimacy as the central theme of the book, the chapter explores how they experience considerable pressures to conform with dominant norms in order to become ‘legitimate’ City workers. While this is relatively straightforward to those who are closer to this dominant group, others adopt a variety of strategies in response, for example, to comply with these pressures, defy them, or try to compartmentalize or combine competing demands that push them away from an authentic self. The chapter concludes that as they are asked to meet this world on its terms, this can lead to a deeply divided self.