Context: Understanding the transition from a novice to an expert has the potential to provide valuable information for young professionals and athletic training educators to aid in the development of tools necessary for lifetime professional learning. Objective: The purpose of this study was to identify and describe the self-regulated learning behaviors of male athletic trainers used to develop expertise in clinical evaluation and diagnosis domain knowledge in athletic training. Design: Descriptive qualitative study using a phenomenological approach. Setting: NCAA Division I and II colleges in NATA District 3 (DC, MD, NC, SC, VA, and WV.) Participants: A total of 20 male n = 10 novice (limited experiences) and n = 10 expert (at least 10 years of experience) athletic trainers in the college setting participated in the study. Data Collection and Analysis: Data were collected using an interview and questionnaire. Data were transcribed and analyzed using interpretive thematic analysis procedures. Member checks, triangulation of data, audit trail, and peer debriefing techniques were utilized to ensure trustworthiness of the data. Results: Three major themes of (1) environment, (2) experiences and goals, and (3) sources of feedback were identified and appear to describe different ways of self-regulating learning behaviors in the clinical evaluation and diagnosis domain. Conclusions: Awareness of the types of experiences needed to develop in the clinical evaluation and diagnosis domain is important to the athletic training profession. The findings of this descriptive study raise questions regarding future study of self-regulated behaviors. Post-professional education might benefit from a better understanding of self-regulated learning but research is needed. (Contains 3 tables.)