Competition has increased in mental health practice. Still, while opportunities in private practice have lessened, school-based mental health practice has witnessed steady growth. Mentoring relationships can serve a critical role in fostering knowledge of school-based careers and about practitioner and higher education opportunities in school psychology. Defined as a process whereby a senior colleague guides, supports, and assists a less developed colleague, mentoring can be critical in fostering practitioner and training careers. This article examines positive contributions of mentoring and provides an example of one successful mentoring relationship involving a 38-year-old student pursuing a graduate program leading to credentialing as a Certified School Psychologist.