Youth workers routinely experience moments in their professional practice with young people when, despite their experience and training, they are simply at a loss for what to do, how to respond, and how to be helpful to the youth. These experiences of not-knowing are seldom shared with other youth workers, which contributes to a climate of shame and humiliation. Professional supervision seldom attends to how youth workers experience these moments and their personal and vocational costs. This study presents a phenomenological investigation of how youth workers experience moments of not knowing what to do, identifies five central themes of the experience, and makes recommendations for improved youth work practice and supervision. This chapter presents the research question and its significance to the field of American youth work.