Young people continue to be espoused as future leaders and contributors to global enterprise employing innovative and creative designs, yet increasing numbers are disengaging and marginalised from educational systems that arguably aim to scaffold and facilitate such capacities. This alarming trend is advancing despite diverse initiatives to re-engage youth which vary in impact and effectiveness. Creative initiatives employing socially critical pedagogies connecting youth life worlds with community, flexible learning options and creative industry, do impact positively on the achievement, wellbeing and access to education and employment for some individuals. Such approaches provide increased opportunities for learning that is productive and generates long term impact despite narrowing curriculum and data driven assessment currently emphasised in education. This paper presents a connected creative pedagogical approach consolidating resources to provide a suite of initiatives connecting youth, local community, councils, education and service providers, creative industries and flexible learning/alternative education. In particular, it offers a discussion of the challenges and opportunities afforded by connected pedagogies centred on youth voice and co-creation, creative arts, transdisciplinary approaches to education, research and place-based community design.