The purpose of this qualitative transcendental phenomenological study is to describe a particular phenomenon: the lived experiences of high school teachers who were responsible for creating and teaching a senior-year English Transition Course. Moustakas’ methods, framework and data analysis guidelines, coupled with interviews using Seidman’s three-interview process, is the best procedure for achieving the research aim. Thus, the study is based upon the results of interviews of 10 high school teachers from schools within a specific geographic region who collaborated with four English faculty members from a comprehensive four-year institution within the same region, over a period of three years. It is important to capture this phenomenon, as it occurred within a time of broad educational reform and uncertainty and will allow others to understand how teachers respond to interventions designed to reduce the need for remediation in reading and writing. This research examines the following questions: (a) What is the essence of high school teachers’ experiences planning a senior-year English Transition course designed to achieve college readiness in reading and writing? Specifically, how do teachers experience planning as a result of collaborative sessions with University English faculty? Additionally, how do teachers experience planning (e.g., course goals, units of study, individual lessons) as result of their individual efforts? (b) What is the essence of the experience of teaching a senior-year English Transition course designed to achieve college readiness in reading and writing? The fundamental textural-structural synthesis revealed four common themes as well as a variety of sub-themes across all participants. Scientific terms were used as metaphors. The juxtaposition of this scientific metaphorical depiction, ostensibly at odds in a study of literacy instruction, intends to reveal the complexity of teacher experiences and the totality of external circumstances as well as internal conditions they encountered. The insights from this study may inform curriculum specialists, policy-makers, school administrators, and English teachers.