Adaptive challenges are ambiguous, systemic challenges that do not have single, technical solutions. We cannot “arrange the deck chairs” and expect to solve adaptive challenges. This conversation with Amy Schweim unpacks a critical issue in her community that was amplified by COVID-19, and how she creatively faced this adaptive challenge. Amy shares how she and her team of leaders help families and children in their community through a new child-care support program that helps children do homework and have fun. Insights include foundations for understanding your community, dealing creatively with adaptive challenges, and the layers of influence that result from facing an adaptive challenge.