This paper reports on a curriculum called New Tech for Youth Sessions, designed for homeless young people, aged 13–25. Motivated by the ordinariness of digital media and its importance in communicating with society's institutions, the primary goal of the curriculum was to develop students' life skills for information technology and digital media. A crucial secondary goal was to position students to recognize their self-worth, through meeting challenges, positive communication with adults, and reciprocal peer support. The paper describes how these goals were addressed by incorporating a community technology center into a multi-purpose drop-in for homeless young people and by a curriculum that guides students through an integrated series of activities related to finding employment. The paper discusses the principles underlying the curriculum, the class processes, and the social structure that supports the learning environment. A far-reaching result, based on offering 13 classes to over 75 youth over 16 months, is the hypothesis that instruction in digital media can create visceral, life-affirming experiences of challenges overcome, which can help strengthen relationships between the youth and the drop-in staff. The paper concludes with a discussion of lessons learned for incorporating digital media into drop-ins for enabling access and for improving life skills.