We express our unease with one-sided invitations into the Northern mainstream, as well as with Southern critics’ retreat into indigenous enclaves of organizational scholarship. We use this dichotomy to theorize the role of context in organizational theorizing by linking scholarly conversations on context, analogical reasoning, and problematizing assumptions. This creates the opportunity to more carefully consider how not just our theoretical backgrounds but also our contextual life-worlds provide the assumptions and analogies we bring into our theorizing. We use this platform to consider in more detail systematic biases in both the Northern mainstream (erasing and imposing biases) and the Southern critique (scapegoating and valorizing biases). These biases have in common that they essentialize context. To address this risk and to facilitate contextual reflexivity, we propose a form of dialogical scholarly engagement to generate complementary spaces to fruitfully question our contextually embedded assumptions.