This qualitative study is concerned with the transition process from school to post-school life for students labelled with learning disability in New Zealand. My interest is in understanding how a particular group of these young people can make a successful transition from school in their search for a good life, as they themselves judge this. I draw on critical social theory to position these young people within contemporary education and society, using a Disability Studies in Education (DSE) framework to understand learning disability as socially, culturally and politically constructed. I draw on Zygmunt Bauman’s critique of neoliberal hegemony and use of metaphor to understand how young people with learning disability are excluded in a contemporary Western society. Post-school outcomes identify very little useful tertiary education or paid employment; long-term reliance on family for living and housing; and extremely limited social networks, mostly founded on family members and paid or voluntary support workers. I argue that these young people are caught in a parallel education system that largely controls and manages them along a restrictive pathway from special education services in schools to special vocational and welfare services post school. The clear voice of the young people through the research findings demonstrates this is not what they want. They want the same opportunities as their peers without disability. Andrew and Caroline, two young people with Down syndrome, and I formed a research team. We came together to explore, understand and respond to an exclusionary landscape during the transition process that I argue leads to unrealised lives. The study utilises a participatory action research approach. It is a collaborative journey and a transformative response to exclusion through what I describe as “the relational dimension.” Further, it is a call to arms on behalf of a particular group of students who have been mostly excluded from rights, responsibilities and opportunities to contribute positively to their lives and the lives of others. This thesis has been a journey of personal and professional, individual and collective discovery. Answers to the question of how young people with learning disability can transition towards a good life are to be found in how we fundamentally value this group of young people in education and society. Valuing can only occur if we recognise our interdependence while acknowledging our unique differences. Only then will we truly provide the opportunities and support that we all need to move forward in our journey towards a good life. This thesis will be of interest to young people; parents; education and social policy leaders; school leaders; career specialists; and all teachers, professionals and support workers in the field. Its findings and recommendations challenge “expert” and deficit constructions of learning disability. They have relevance for a collaborative “whole-school” approach to career and transition policy and practice for students with learning disability; importantly, however, they also have relevance for all students. Effective relationships are central to understanding how, through our relative interdependency; we can collaboratively make the journey towards a good life. Additionally, the thesis contributes to knowledge regarding how to meaningfully involve young people with learning disability in the research process through their lived and our shared experiences that provide ethical, methodological and procedural insights. I develop two main arguments in this thesis. My first argument is that exclusion from educational opportunity must be exposed, challenged and rejected. Exclusion must be exposed in order to understand the unequal power mechanisms at play. Exclusion must be challenged, as the outcome of these unequal power mechanisms is that some students succeed and some fail. Exclusion must be rejected to make way for new relational, transformative education agendas. My second argument is that direct and meaningful involvement and collaboration by young people with learning disability in the research process will support practical solutions towards greater democracy in education and society. The ultimate outcome of democracy in education is a system where all students are valued and celebrated for their unique differences and stories, yet with recognition of their relative interdependency. All students are viewed as capable, purposeful, responsible and contributing. They are provided with the opportunities and support required to realise a good life, leading to active contribution and a sense of belonging in education and society.