This narrative inquiry examines why a well-respected English as a Second Language teacher quit teaching in an urban middle school in advance of her retirement. The work provides interpretive accounts of what attracted the teacher to start teaching ESL, what caused her to stay in the profession and the circumstances that drove her to quit. In the fourth largest city in the U.S. where the research unfurled, urban teacher attrition is a burgeoning experienced teacher phenomenon as well as a beginning teacher trend. The same can be said for other urban cores globally. Ashley's stories of starting, staying and leaving teaching as an experienced and much-loved professional makes important knowledge contributions having to do with: (1) unfolding lives, unfolding social movements, unfolding educational trends; (2) different threads of experience and the making of a life; (3) ESL teaching and social justice; and (4) teaching metaphors and images.