In this paper, we revisit the long-standing debate of whether there is a pattern in the evolution of organisms towards greater complexity, and how this hypothesis could be tested using an interdisciplinary lens. We argue that this debate remains alive today due to the lack of a quantitative measure of complexity that is related to the teleonomic (i.e. goal-directed) nature of living systems. Further, we argue that such a biological measure of complexity can indeed be found in the vast literature produced within life history theory. We propose that an ideal method to quantify this complexity lays within life history strategies (i.e., schedules of survival and reproduction across an organism's life cycle), as it is precisely these strategies that are under selection to optimise the organism's fitness. In this context, we set an agenda for future steps: (1) how this complexity can be measured mathematically, and (2) how we can engage in a comparative analysis of this complexity across species to investigate the evolutionary forces driving increases or for that matter decreases in teleonomic complexity.