Research has demonstrated the cognitive and mental health benefits of learning new skills and content across the life span, enhancing knowledge as well as cognitive performance. We argue that the importance of this learning – which is not available equally to all – goes beyond the cognitive and mental health benefits. Learning is important for not only the maintenance, but also enhancement of functional independence in a dynamic environment, such as changes induced by the COVID-19 pandemic and technological advances. Learning difficult skills and content is a privilege because the opportunities for learning are neither guaranteed nor universal, and it requires personal and social engagement, time, motivation, and societal support. This paper highlights the importance of considering learning new skills and content as an important privilege across the life span and argues that this privilege becomes increasingly exclusionary as individuals age, when social and infrastructural support for learning decreases. We highlight research on the potential positive and negative impacts of retirement, when accessibility to learning opportunities may vary, and research on learning barriers due to low expectations and limited resources from poverty. We conclude that addressing barriers to lifelong learning would advance theories on life span cognitive development and raise the bar for successful aging. In doing so, our society might imagine and achieve previously unrealized gains in life span cognitive development, through late adulthood.