We are, apparently, living in unprecedented times, an Age of Uncertainty, when wicked problems whirl all around as we struggle to cope with Covid-19, environmental catastrophe and the right-wing populism that threatens to unravel all kinds of international agreements. In this personal reflection, 15 years after I wrote an article on wicked problems and the social construction of leadership, I take a look back, and forward, to see whether there ever was an Age of Certainty when only tame problems temporarily troubled us, or whether our understanding of the world is itself a social construction, open to dispute and thus we have always lived in uncertain times. In the process of this evaluation, I consider whether collaborative leadership, often associated with wicked problems, is as ubiquitous and effective as some proponents make out, and if it isn’t, what this says about our ability to address such problems.