The sequence of professional development within psychology from doctoral education to first job represents a period of remarkable professional and personal growth for each trainee. However, this sequence also contains a variety of barriers that hinder progress through the pipeline. The myriad individual-, program-, and system-level barriers encountered by trainees in health service/other applied service psychology and in research basic/applied psychology are identified. To actively and systematically facilitate improved passage through major transition points, individual trainee and trainer, program- and system-level action steps are recommended. In addition, emphasis is placed on ensuring that the psychology education and training culture prioritizes the progress, creativity, and flourishing of trainees and supports their movement through branching pipelines in their training and in their careers.