In 2014, Tembusu College, one of the residential colleges at the National University of Singapore, introduced self-reflection workshops in its programme for third-year students. These grew into a series of five 2-hour sessions, conducted every semester in small groups led by fellows and graduate fellows. This chapter provides one former faculty member's perspective on the value of convening self-reflection workshops in the residential college setting. It also draws on a qualitative assessment study of the workshops that was conducted in the academic year of August 2016 to May 2017, based on 21 interviews with students from different cohorts. Using the framework of the “authentic career” (Hall & Mao, 2015), the chapter argues for the importance of self-reflection, not only to help prepare students for the world of work but also for their development as unique individuals. It also shows the benefits of practising individual and relational authenticity in this way to extend from participating students to fellows and the broader college community.