This paper's commentary is guided by Gramsci's distinction between, on one hand, the pessimism of the intellect and, on the other, optimism of the will. Accordingly, we seek initially to convey some of the intractable challenges that tend to be encountered by school leaders in the contemporary education context. In doing so, we argue that these leaders can no longer rely exclusively on codified knowledge, but require more flexible approaches to leadership engendering new ways of learning, dispositions and behaviours. In keeping with the optimism of the will, we then examine ways in which professional learning for school leaders may be enhanced to deal with the complexities identified. For this purpose, we describe a more personalised approach to school leaders' professional learning than has been customary, harnessing knowledge, dispositions, and performance deemed valuable for leadership in more complex circumstances. In particular, the importance of school leaders developing self-agency in their learning is emphasised. Contiguously, attention is devoted to ways in which metacognitive awareness may be acquired so that experiences present opportunities for learning. This agenda, we argue, encourages school leaders to take responsibility for, and ownership of, their own professional learning, undoubtedly an essential backdrop to the learning of others.