This book is the third collection of essays by behavioural scientist Professor David Chan, most of which first appeared in The Straits Times. Endorsed by fifty leaders from different sectors, this book provides a powerful springboard for self-reflections, sense-making, internal and public discussions, and individual and collective actions. A common theme that runs through these essays may be described as "Meaning Matters" which refers to the content and subject matter of the critical issues experienced by people and what it means to them. It is also about why the way that people think, feel and act as they make sense and meaning of their experiences should matter to individual well-being and societal progress in Singapore. This book goes beyond examining what critical issues mean or matter to people, policy making and nation building, and why they do, to focus on translating the "what it means" and "why it means" to "how it means" and "when it means".