Navigating the intersections between personal and professional identities can be a challenge throughout one’s professional development but especially during challenging life transitions such as divorce. We share two stories highlighting our own experiences navigating this particular hurdle, as well as the distress with which we struggled that was difficult to admit in a professional setting. Discussed are ethical implications for handling impairment in competence in self or colleagues, as well as a strengths-based framework to encourage psychologists to focus on aspects of well-functioning as a matter of practice. Well-functioning refers to “the enduring quality in one’s professional functioning over time and in the face of professional and personal stressors” (Coster & Schwebel, 1997, p. 5), which allows one to maintain personal wellness and appropriate professional functioning. We examine the literature on impairment among psychologists and share specific strategies for employing elements of well-functioning to navigate challenging times in life. We conclude with what we learned from our own journeys that may benefit other psychologists experiencing personal difficulties. (PsycINFO Database Record (c) 2019 APA, all rights reserved)