What happens when a teaching artist ends their studies unprepared? How do theater teaching artists navigate unpreparedness in their work? Using three personal vignettes, we explore reflexivity toward our own unrehearsed moments and contextualize our experiences within teaching artist preparation literature. From learning how to 'show up' as a teaching artist, to navigating school policies around 'deserving' participation, to reaching the bounds of their therapeutic training as non-clinicians, we re-encounter moments for which we were unprepared, despite extensive preparation and education. Ultimately, we suggest key questions that teaching artists can reflect upon in such moments, in the hopes of building more reflexive practices, programs, and policies in the field of teaching artistry.