In this chapter, the authors present their case study to explore what Parker Palmer calls the inner landscape of teachers. They explore the inner landscape of students reported in research studies conducted by various members of the Transdisciplinary Phenomenology Research Group as well as others. The findings from these studies provided valuable insight about students’ experiences, suggesting that their teachers were unaware of messing up in their approaches to such learners. The authors provide studies of African American students on a predominately white campus, international student experience in American higher education, and low socioeconomic status and first-generation students in community college and university settings. They discuss how messing about with a phenomenological approach can avoid or overcome a messed-up learning environment. The authors show that a phenomenological approach to teaching and learning can further healthy relationships and a sense of belonging in the lifeworld of the classroom.