Viewed one way, Alan Schoenfeld's main lines of research and Katherine E. Lewis's dissertation have almost nothing in common. Schoenfeld work has focused on understanding mathematical thinking and teaching, while Lewis' work has focused on mathematical learning disabilities. Viewed another way, there are strong overlaps and strong parallels. In this reflection they explore the similarities and characterize how each of them developed a sense of self as a researcher. They describe the somewhat meandering path each of them took to their current areas of scholarship, reflect upon how their "outsider" status afforded a novel perspective on the questions they care deeply about, and discuss the affordances of the apprenticeship model for their own teaching and learning.