Through five in-depth interviews with soon-to-be or recent graduates of elite colleges and universities, this study finds that respondents look down upon money as a value but temper their judgements according to their understandings of privilege and marginalization. Relying on Shame’s (2017) framework of millennials as rational actors making cost-benefit analyses when making career choices, this study finds that passion, work-life balance, altruism and pay are four salient values that guide respondents’ work choices. Respondents judge themselves and one another according to the idea of selling out: giving up on personal values for money. They identify a paradox of privilege in selling out: Both the choices to sell out and not to require different forms of capital. Respondents therefore temper their judgements based on people’s socioeconomic status and other identities. Respondents also use comparisons to sell-outs to position themselves as authentic individuals with agency and varying levels of autonomy.