Although we may claim our students are developing a sociological imagination, it is quite another to realize this in our teaching and our students’ performances. Through a professional move from teaching in Chicago to Maine, I was led to rethink how I teach the sociological imagination. I argue that if we are to teach the sociological imagination, we must consider our students’ contextual backgrounds more carefully and use student’s lived experiences as “text” from which they exercise and develop their sociological imaginations. I illustrate this approach with an assignment designed to use students’ experiences from rural and small towns in Maine. The assignment challenges them to use their sociological perspective to look at the relationship between “private troubles” and “public issues,” and to demonstrate using a sociological imagination to reflect on their biographies.