Child care—the care, education, and support in the growth and development of our youngest residents—currently hangs in the balance. Although their work is both skilled and valuable, early educators have been and continue to be among the most poorly compensated workers in the country, with some of the lowest wages and typically without access to benefits. While those working in the early-childhood sector have been vocal in their interest and need for health care, paid time off, and retirement plans, less is known about the practical policy options for providing these types of benefits to early educators. Through conversations with 11 local, state, and national leaders and innovators at the intersection of child care and labor, I identify the challenges—and the possibilities—for providing retirement benefits to early educators, given our fragmented child-care “system.” Understanding the challenges and the barriers on the individual and organizational levels, as well as the potential on the institutional level, may help us begin to take stock of the landscape for funding and delivering retirement plans and for creating pathways to turn these “bad jobs” into “good jobs.”