Pediatric postgraduate medical education typically occurs during the second and third decades of life when many people are planning on starting and raising families. Thus, it is of utmost importance to foster healthy and supportive systems for trainees to obtain time off and receive the help needed without added stress and difficulty. In pediatrics, a specialty that aims to have optimal health for all children, we are acutely aware of the required support parents need to raise healthy children and are uniquely positioned to lead graduate medical education in family-friendly policies and practices. In this chapter, we will review historical perspectives of residents as parents, literature from the perspective of the trainee, and evolution of expected and granted time off for parental leave during postgraduate medical training. Parental leave will be discussed in depth, as will “return to work” considerations, including highlighting the current state of requirements and best practices for parenting electives. Exploration of lactation support practices and childcare practices will be reviewed, as well as systems that work well for trainees regarding wellness and satisfaction with training. Finally, we will explore the incongruence of time-based training with emerging competency-based medical education (CBME) systems.