This essay explores the tension between pursuing meaningful work in instruction librarianship and the realities of working in a society in which many jobs provide little fulfillment or pleasure, or, as the journalist Sarah Jaffe puts it, "Work won't love you back." Drawing on a recent conference keynote by Anne Helen Petersen, C. Wright Mills's conception of sociological imagination, and an ecological model of teacher agency, I propose that one way librarians can sustain their teaching practices and preserve their well-being is by actively investigating how social structures and relationships influence their teaching roles.