This article is about three adult authors who are making meaning of their experiences as early career, tenure-track professors. All former secondary English language arts instructors who are responsible for preparing future secondary English teachers, the authors use Mezirow's transformative learning theory lens to examine their trajectories from doctoral students to early career professors, focusing on how they navigate the alignment--or lack thereof--between their expectations and their realities, with attention to disorientation and guilt, culminating in critical examination. They have learned to create new spaces for themselves and to redefine their roles according to new knowledge, highlighting the importance of developing a mentoring framework that can help make others' progress through these phases less difficult. The authors offer suggestions for how to use transformative learning theory to create conditions in which they and their mentees can experience a professional lifetime of satisfaction.