The modern world abounds with new career options and associated education pathways. The jobs landscape confronting today's school students looks unfamiliar and potentially confusing to many parents. Unlike in their parents’day, few ‘good’ jobs are waiting to be filled by students coming straight from school, even with Year 12. This presentation describes a project which provided accredited training for a small number of parents and community members to run career and education pathway information events for parents in disadvantaged communities in Northern Tasmania in association with schools. It discusses the challenges faced in recruiting the ‘lead parents and community members’ from within communities where adult self-confidence as learners tends to be low, and education and training are often seen as things that people ‘from other places do’. Challenges can be addressed by ensuring individuals offering the training are seen to be credible and to understand the context of those living in these places. The use of boundary crossers, who understand the community context, speak its language and are trusted by the community, helped recruitment. Those who took the plunge and participated in the training reported benefits including increased self-confidence, increased awareness of educational options and pathways not only for their children but themselves and confidence to engage in their child’s education and learning beyond the classroom. Parents who attended the events organised reported a greater awareness of post-year 12 education and career pathway options beyond their own experiences, and confidence that the education their child was receiving was a high quality education. Tailored events provided non-judgmental support, guidance, resources and networks aimed to assist parents support their children’s educational and career aspirations in a safe and meaningful place-based environment. Time, persistence, patience and working alongside parents as education partners, are key attributes for educational institutions doing this work.