Literature proliferated about teaching as coaching, guiding, and facilitating. Teachers who desire to recapture the joy that can be found at the heart of teaching and learning may wish to consider a phenomenological approach. In this chapter, the authors focus on one aspect of a phenomenological approach, as exemplified by their case study professor. They examine his specific practice of instructional planning for class sessions during an academic semester. The professor hoped that students’ experience in the seminar would go beyond mere intellectual engagement into the existential dimension of transformative learning. Personal factors that relate to instructional planning practices include a teacher’s theoretical perspective, need for power and control in the classroom, enthusiasm for learner-centered approaches, and willingness to take risks regarding nontraditional teaching strategies. The authors look at instructional planning obtained through the data of their case study research project.