I conducted this autoethnographic research study to explore how I as a freshman orientation instructor meandered into college teaching through writing, which I used to develop my pedagogical content knowledge. Focusing my research as college faculty development, I reached back in the past and also in the present to select particular experiences to portray as vignettes, thus creating a kaleidoscopic lens. This kaleidoscopic lens serves to provide insight into my perspective of how my teaching philosophy based on the use of writing prompts developed. By connecting the personal experiences that had established my teaching philosophy using writing prompts to the classroom culture of first year students in a northeastern Alabama public two-year community college, the scholarly significance will be perused through integrating the theoretical framework of Lee S. Shulman’s (1986, 1987) pedagogical content knowledge (PCK) with additions of Otto and Everett’s (2013) context knowledge and Zepke’s (2013) threshold concepts. I as a differently-abled instructor-researcher self-narratively depict how writing prompts supported my teaching experience as pedagogical content knowledge. Thus, my use of writing prompts as pedagogical content knowledge is purposefully intended for providing significant learning experience for my students, improving their readiness for writing college papers and also for communication skills as a potential employee and productive citizen. Over the course of spring and fall 2015 terms totaling four different seventy-five minute Orientation 101 courses, the data purposefully sampled from the students’ written responses to the prompts given and also from dyadic interviews with several peers ranging from active and retired faculty to acquaintances serve to support my own perspectives and experiences that determine use of writing prompts as effective pedagogical content knowledge.