Various abductive research approaches have been foregrounded in the literature in recent years. This paper joins the literature on engaging with abductive research approaches, and proposes the term of 'informed guessing' as a way to think about enacting educational research abductively to allow new concepts, ideas and insights to come into being. Informed guessing is triggered by a surprising encounter, and the researcher attempts to understand that encounter (a little) differently by making relations and connections among disparate entities (e.g. concepts and objects). In informed guessing, theories and concepts play an important role by allowing one to refer to 'invisible' structures as well as for the enactment of defamiliarization, which allows for alternative understandings. Informed guessing is illustrated through an instance of my research enactment on the U.S. school choice lottery system. I conclude by raising concern about the relation between abduction and deduction in informed guessing.