The studies presented in this dissertation have shown that fostering the vocational identity of at-risk youth can be improved when their different individual characteristics are taken into account and when preferences of at-risk youth and their mentors concerning mentor qualities are addressed during mentoring sessions. Tuning in to these differences and needs implies customization in programming and mentoring. This dissertation has contributed to efforts to reconnect with at-risk youth and keep them on track at school and work, resulting in better future prospects and an independent and sustainable position in society.