This chapter presents an autobiographical account of the career of Aaron L. Pincus, PhD, particularly as it relates to his achievements in psychology generally, and personality assessment more specifically. Aaron Pincus received his bachelor’s degree in psychology from University of California—Davis in 1985, his Master’s degree in personality psychology from University of California—Berkeley in 1987, and his doctorate in clinical psychology from the University of British Columbia in 1992. He has spent his entire faculty career at Pennsylvania State University where he is a full professor. First, an account of his personal and professional development is provided. This is followed by an articulation of Aaron Pincus’ approach to personality assessment. The chapter concludes with discussion of the experiences, mentors, and collaborators that influenced Pincus’ career and approach to personality assessment.