Paul's reference to his adaptability to different groups in 1 Cor 9.19–23 is central to recent discussions about Paul's Jewishness. This paper argues that the crucial context for Paul's metaphor of self-enslavement (1 Cor 9.19) is not to be found in anthropological passages such as Rom 6 or Gal 5, but rather in the conditions of a slave's life in antiquity. This leads to an interpretation that combines essential concerns of a Paul within Judaism perspective with those of more traditional exegesis.