Scientific breakthroughs and the ceaseless pace of technological innovation touch a diverse range of subject matter, with the most profound changes often proving to be the most controversial. Recent decades have seen the fields of biotechnology and information technology raise the most attention, with the deliberations of lawmakers and courts being increasingly focused on issues brought up by innovation within these fields. Though seemingly disparate and autonomous, given the wide range of issues brought up by the different facets of contemporary technological innovation, the author in this special comment presents how one can take an overview of the subject of regulating technology vis-à-vis the law. Drawing inferences from his experiences with such issues during a law reform and judicial career spanning several decades, the author argues that there are interconnected paradoxes, and also general lessons, that regulators, particularly judges filling in for gaps left over by the legislature, must keep in mind when dealing with the subject of regulating technology.