Many job applicants spend an inordinate amount of time struggling with the task of fashioning the most appealing biography of the increasingly skillful self out of interwoven genres that can also circulate individually. These struggles are most frequently articulated as questions of how best to manage different genres’ chronotopic expectations. Under neoliberalism, how workers are expected to represent their previous work lives has shifted significantly from earlier moments of capitalism: they are now expected to represent themselves as entrepreneurial selves. Over and over again in various workshops about job applicant genres, participants’ concerns over how to represent their employment history via different genres became the focus of the workshop. The focus on mastering a genre’s chronotopic expectations stood in for job applicants’ anxieties over representing themselves as the ideal neoliberal employee. The standardization and abstraction of time and the neoliberal expectations now linked to these genres has led to predictable conceptual quandaries for job applicants about how to connect oneself in appropriate ways to previous contexts that become articulated as dilemmas surrounding the pragmatics of producing genres’ chronotopes.