Leadership in the Australian arts and cultural sector has become, in recent decades, a prominent topic of discussion. On one hand, there is increased corporatisation in the arts that promotes leaders with strong business orientations, on the other, questions asked about the role arts leaders play in shaping our cultural and intellectual life. In these debates, we are left wondering what constitutes effective arts and cultural leadership, and how we develop it. While there is substantial research on leadership in arts and cultural organisations, it focuses predominantly on established leaders and often neglects large sections of the industry where leadership is practiced in flexible, often precarious, labour markets. We know little of how arts and cultural leaders are developed in the context of sole traders, casual workers and volunteers who are unlikely to access leadership development through traditional channels discussed in management literature. This research explores the development of leadership identity within the Australian arts and cultural sector examining nine disciplinary based cases that are within, across and outside the more frequently researched organisational context. Interviews were conducted with 41 practitioners in the disciplines of theatre, film, music, advertising, digital design, design and craft, visual arts, festival and event curation, and fashion and blogging. It uses social constructionist theories of leadership, identity and development as a theoretical lens to demonstrate how emerging leaders develop an often-complex relationship with leadership. In the face of identity regulation, or intentional social processes that impact identity construction and reconstruction, some arts and cultural emerging leaders demonstrate resistance to identifying as a leader, even when engaged in leadership practice. Building on critical approaches to leadership and leadership development, this thesis establishes that emerging leaders who engage in communities of practice, or collaborative practice that involves joint enterprise, mutual engagement and shared repertoire, are less likely to be reluctant leaders. Leadership identity development within communities of practice offers a space for positive construction of leadership identity within creative practice, mitigating against identity regulation, broadens leadership understanding and provides alternate strategies to the more individualistically oriented leader development models found in industry and organisational theory. From the case studies, five leadership personas are formulated that demonstrate differing relationships arts and cultural workers have to leadership. This research contributes to theories of critical leadership and leadership development, particularly in the arts and cultural sector, while also offering practical recommendations to enhance industry-based leadership development.