Like art, ethics can be a complex and scary mirror that forces us to consider, practice, and profess specific choices that speak to who we are and what we value. The author of this article observes that confronting specific ethical dilemmas within her work with young people has brought various tensions to the forefront of her practice as a Teaching Artist. What is responsible representation and is it culturally, individually, and/or site specific? What are the goals of our drama work with youth? To whom are we ultimately responsible when facilitating drama and theater with young people? Who and what must we consider when participating in meaning making through the arts? These issues proved central to the author's work as a resident teaching artist for "Place: Vision & Voice" (PVV), a community-based digital storytelling and performance residency program. In this article, she confronts the complex ethics of cultural representation in a drama project with Native American youth.