This study explores teacher retention and teacher resilience in the United States through the stories of five teachers. The researcher presents the research in two manuscripts. Finding My Way through Teaching: A Critical Autoethnographic Play combines critical pedagogy (Freire, 1970) with autoethnography (Ellis, 2004) to examine the author's personal journey as a teacher in a private school, a public school, and a public school in Central America. The research is presented as a one-act play with scenes focusing on conversations with parents, principals, and students, along with scenes examining each situation that take the audience through the internal monologue of the researcher's decision making process to move schools, stay in a school, leave a school, and question their ability or willingness to return to K-12 schooling. Building Relationships: The Stories of Four Small Urban School Teachers shares the stories of four veteran elementary school teachers, teachers who have taught for more than five years, from Parker City Public Schools. This study uses a case study approach with recorded dialogic interviews as data (e.g., Kvale, 1996; Marshall and Rossman, 2011). The stories the teachers tell point to the importance of building and maintaining relationships with students, other teachers, and administration, as one of the key factors for overcoming the challenges of working in a small urban school division and one of the key factors for changing schools or remaining in a school throughout their careers.