Aim: This paper aims to show the interaction between the young person, their family and the school, in the aspect of career awareness and development of young people with special educational needs (SEN). Method: Three students with SEN from one secondary school in Singapore participated in this study. A series of three interviews were conducted with students using educational journey mapping and photo/ journal elicitation techniques to empower the students to share their experiences. Their families, teachers and other school personnel from the secondary school were also interviewed. The interview transcripts and other ethnographic data were analysed and thematically coded to arrive at both generalisable and individualised descriptions of the experience. Findings: Three metaphors were identified as a representation of each student's lived experience in finding a suitable career, that is, 'training for a triathlon', 'engaging in a tug-of-war' and 'performing a juggling act'. Work and volunteering experiences, selection of vocational studies, and planning ahead in vocational college were also identified as key areas of experience. Limitations: This is an exploratory study that worked with a small number of participants. Therefore the findings will not fully represent the range of experiences currently faced by young people with SEN. Conclusions: The ease of which the student participants were able to develop career awareness and goals were dependent on the collaborative efforts of both school and family settings. The study also showed the importance of listening to the voices of families and young people, and provides suggestions for practitioners working with families, schools and young people.