How to teach data science effectively is still largely unknown, as is the experience of educators in this field. Many data science instructors transition from practitioner roles, and understanding their experience during this transition may inform us of ways to support these individuals. To study this, I transitioned from data science practitioner to educator and tracked the experience with journal entries. The study found that I encountered many challenges, mainly surrounding issues of teaching in a higher education context, caring about others opinions, and difficulty distinguishing identity between peer, TA, or instructor.