The art of holding complexity is the ability to face conflict and other life challenges through collaboration, self-awareness and flexibility rather than through control and coercion. Holding complexity is a key theme identified in a research project exploring educator identity and development in practice in a system of alternative or ‘flexi schools’ in Queensland, Australia. Flexi schools support young people to create positive education pathways after experiences of failure and/or exclusion from conventional schooling. This paper explores the concept of holding complexity and how educators develop this capacity in their work. Design experiment methodology was used to explore how ways of working and professional learning in flexi schools influenced educator identity and development and how induction needs of new staff could be addressed. Educators enfranchising young people in flexi schools face challenges that require different ways of working that are young person-focused; that shift power dynamics and require adults to adopt a position of co-learner and facilitator. Holding complexity enables educators to support young people who face multiple issues that impinge on their ability to engage in conventional schooling. Induction and professional learning programs emphasising the art of holding complexity assist flexi school educators in their work with young people.