Progress in altering the current obesity epidemic among children and adolescents remains elusive. Evidence continues to underscore the challenges of altering weight status as children age. Further, weight loss interventions among children and adults alike tend to demonstrate efficacy in the short-term, however individuals tend to slowly revert back to their original weight status over time. New understanding of obesity's early origins suggests the need to rethink current approaches, particularly within healthcare. Instead of a predominant focus on "mid-flight course corrections," healthcare should consider the "take-off" time period for health trajectories. This means improved support and promotion of healthy behaviors before and after birth, and with both the mother and infant. To meet the challenge, greater continuity will be required across obstetrics and pediatrics, which often operate independently, focused on different clinical outcomes. Likewise, there is an urgent need to remedy a significant skills gap within both practices. Through its connection with almost every new mother, healthcare plays a unique and vital role in maternal and child health outcomes. A more seamless obstetrics-pediatrics care continuum could better address the early origins of obesity, factors that we are coming to learn have life-long consequences.