School leaders navigate a multiplicity of frameworks, roles, and expectations. The destination of school leaders is a complex and moving target, hard to pin down and even harder to set course for due to the complexities of the constantly moving parts of the reality of leading schools. The Australian Professional Standards for Principals reflect the overwhelming expectations placed on school leaders, who must be across global and local issues, curriculum, professional standards, policy, and wellbeing of all in the school community. Principals and senior school leaders constantly code switch between strategising, leading, teaching, administrating, coaching, counselling, complying, mediating, resolving, gatekeeping, resourcing, and negotiating. They are expected to align ethical action with coherent vision, deep understanding of context, and a working knowledge of education research. They are expected to be unwavering in their moral purpose and in the transparency, consistency, and logic of their decision making. As two senior leaders of pedagogy, curriculum, and staff development in schools in Australia, we authors bring to this chapter our lived experiences of school leadership. In addition to our leaderly identities, we explore our simultaneous researcher identities as, post-PhD, we continue to moonlight as researchers, academic writers, and academic readers. We are both also parents of primary school aged children, a role that influences how we approach leading. In this chapter, we explore the metaphor of wayfinding as a lens to theorise how school leaders navigate concurrent and complementary identities to lead with purpose, compassion, knowledge, and intentionality, in ways that are sustainable for themselves and their schools.