This lecture examines the sustainability of policies determining the future of Singapore’s most important resource: people. It focuses on two issues at opposite ends of the life-cycle spectrum: on one hand, how to provide for older people in retirement, and on the other, how to make more babies. What fundamental policy assumptions could we reconsider as we plan for the retirement adequacy of what is one of the fastest ageing societies in the world? What improvements can we make to our social security net so that we have a more robust and inclusive system? How far are we willing to go to arrest our flagging total fertility rates? These fundamental questions are addressed in the context of ageing and starting a family in Singapore over the next fifty years, as the continued sustainability of our population and the dignity with which we allow our elderly to retire in underpin our demographic challenges.