The school-to-work transition is widely acknowledged as difficult, requiring meaningful support for young people to navigate successfully. This paper examines the reported experiences of six families navigating 23 home educated young people's transition from compulsory education to tertiary education and work. Data from semi-structured interviews with the parents were thematically analysed using Bourdieu's "habitus, capital," and "field." Findings indicate that the parents provided ample opportunity for self-exploration to encourage autonomy coupled with opportunity to explore and participate in the wider community, leading to a successful transition experience. The findings suggest that a contrasting, alternative career preparation method can be successful; one that values autonomy over the traditional approach which involves a scaffolded set of knowledge and skills. This study indicates that the transition can be successfully facilitated by providing young people with opportunity for autonomous self and career exploration in the community, without the standardised assistance provided through schools.