Dr Cheong Koon Hean, CEO of the Housing and Development Board (2010–Present) was the Institute of Policy Studies' 5th S R Nathan Fellow for the Study of Singapore. This book contains edited versions of the three IPS-Nathan Lectures she gave between March and April 2018, and highlights of her dialogue with the audience. Climate change, an ageing population, anti-globalisation sentiments the world over, technological disruption, and social media all pose unique problems and opportunities to cities. Dr Cheong examines how cities deal with their urban challenges to create a better life for their citizens. In particular, what are the considerations needed to plan and develop Singapore in the face of rapid change and uncertainty, given our constraints as a small city-state with an open economy? The IPS-Nathan Lectures series was launched in 2014 as part of the S R Nathan Fellowship for the Study of Singapore. The S R Nathan Fellow delivers a series of lectures during their term to advance public understanding and discussion of issues of critical national interest.