This paper will review how I have used writing to process moments of tension or uncertainty with three clients: Eddie, C. F., and Kayla (names changed). In what follows, I will first give a brief background sketch of the client, share parts of a client’s stories from my own reflective writing and then present the core concepts from those theorists who helped me make sense of what had occurred, thus guiding my work with the client. I met each of these clients while working at their high schools on the South Side of Chicago.