The purpose of this article is to share the lessons learned from two life threatening illnesses I experienced just before and just after becoming a practicing psychotherapist. These experiences profoundly transformed my personal and professional trajectories. I will describe the details of my experience and then share the lessons and transformations that I continue to reap since being diagnosed. It is my hope that clinicians, supervisors, and professors might glean insights from my experience of serious illness as a graduate student and early career psychologist as to how they might support their colleagues, students, and patients when they face significant health issues. (PsycINFO Database Record (c) 2019 APA, all rights reserved)