This book examines contemporary policy debates from opposing perspectives. It considers seven key topics in today’s society: land use, education, international trade, health insurance, technological change, and recreational alcohol and drugs. Two scholars with differing viewpoints discuss each topic, one working in the classical liberal tradition and the other advocating slower, incremental societal change. While classical liberalism historically presents a vision of society comprised of free and responsible individuals, this book shows the importance of considering the nuances of this vision today. Beyond theoretical regulation vs. de-regulation debates, the book highlights challenges for classical liberals by considering how dynamism and creative destruction may disrupt communities, leading to worse outcomes for some groups. This edited volume aims to deepen understanding of this challenge to a free society and partake in and encourage civil intellectual discourse and debate. It will interest students and scholars from various fields, including economics, political science, public health, and environmental studies.