In this episode Eric and Garth host an invited panel at STP’s Annual Conference on Teaching (ACT) 2023 featuring Loretta McGregor (Arkansas State University), Skyler Mendes (Arizona State University), Janet Peters (Washington State University), and Jordan Wagge (Avila University). This session was organized to explore the diversity of careers and career stages within psychology, which includes a discussion of both career challenges and career successes. Worries about the future of our profession are expressed, as well as the importance of cultivating the next generation of psychology educators. Each participant shared important mentoring experiences in their careers. This was followed by question and answer with the audience, where topics such as the complexity of intersectionality, Psychsessions contributions, and a hypothetical “do-over” in one’s career were among the topics addressed.