For 17 years, I worked with adolescent male sexual perpetrators in residential treatment, where the predominant modality is cognitive-behavior therapy. Concurrently, I completed training to become a psychoanalyst, and began providing psychoanalysis and psychodynamic psychotherapy to children and adults in my independent practice. I initially thought it coincidental that I started working with perpetrators and definitely considered the work a separate path in my professional development. This article will explore the development of my dual professional roles, how my psychoanalytic orientation informed my work with juvenile sexual perpetrators, and how my work with perpetrators both informed and collided with my private psychoanalytic practice. I will provide clinical illustrations, using pseudonyms for my clients and deidentifying and disguising their material, while retaining their dynamics and clinical process. I will share some of what I learned about them and, ultimately, some surprising things I learned about myself in the process. These insights were transformative in that they shed light on both my empathy and blind spots, helped me to understand my motivations to become a psychoanalyst and work with perpetrators, and propelled my psychological and professional development. It is hoped that these insights will be of assistance to other psychotherapists in their professional development. (PsycINFO Database Record (c) 2019 APA, all rights reserved)