This book is a collection of essays by thought and advocacy leaders, policymakers, and academics in Singapore who have been and are in positions of influence in shaping social policies, and hence the social context, in the country. These essays are meant to initiate discussion, promote debate and broaden understanding of the social issues at play, the challenges faced, and the trade-offs involved in enhancing social policies, strengthening the social compact, and shaping the social context in Singapore. This is done through addressing issues and challenges in (1) Government and Civil Society; (2) Education; (3) Employability and Employment; (4) Social and Family Development; (5) Demographics and Social Spending; (6) Healthcare and Healthcare Financing; (7) Urban Planning and the Environment; (8) Disruptions, New Technologies and Smart Nation. It is hoped this book will be useful for students of sociology, social policy or public policy, as they discuss the dynamics and trade-offs involved in planning, shaping and implementing social and public policies in Singapore. This book also hopes to inform and initiate dialogues among Singaporeans on the social issues and challenges we face in our city-state and which we have to collectively address as a nation.