This article discusses the impact of critical work education and social exclusion in aiding and assisting school-aged children and young adults through projects that help reshape their connections to self and society. The visual and performing arts gave at-risk young people opportunities to explore their biographical histories and personal experiences. Teens and young adults were provided spaces to express their world in ways that showcased peer productions. The arts provided democratizing influences and allowed the participants to reach outward to new communities of individuals and to new venues for these forms of cultural work. Young people reacted positively when their works were legitimized in community projects. Within these youth development projects, critical work educators offered students control, ownership, and freedom of expression, particularly in relation to career orientations and job readiness.