This reflective paper explores a personal experience teaching a developmental English course through John Dewey’s reflective lens and an attempt to identify, define, analyze, solve, and test an unexpected problem encountered in the classroom. The issue identified was that students were not transferring learned writing and editing skills to major assignments or using said skills in other courses they were enrolled in. This led to examining the lack of experience teaching Alaska Native English learners and a lack of knowledge of student cultures and backgrounds. Through research and cultural training, the decision was made to add an element of knowledge exchange in the classroom by giving students the opportunity to teach about who they are and their culture and languages. Class content contained no connection to Alaska Native culture or way of life until Dr. Barton presented the Standard Model for Indigenous Learning (SMIL). There was an understanding that the curriculum did not need to be redesigned entirely but rather incorporate the five threads of SMIL into the content already created. Possible hindrances embedded in curriculum design were also explored and with the discovery of the importance of giving students the time and space to practice the application of skills taught in the classroom on major assignments. Through this reflective practice journey, self-reflective questions led to culturally responsive instructional strategies to target academic readiness skills supporting Indigenous Alaska Native first-generation students to reach course goals.