Work preparation should provide adequate qualifications for sustained labor market participation and lifelong learning that lead to economic self-sufficiency and positive engagement as family members and citizens. Five barriers to productive transitions confront disadvantaged urban youth: changing structure of employment opportunity; skills mismatches in urban areas; employer discrimination; negative influences of family and neighborhood life; and weaknesses within youth-serving institutions. Ten lessons from research and practice address these barriers: modest interventions have modest and short-lived impacts; second-class systems yield second-class results; traditional didactic teaching methods fail significant numbers of young people; work is a powerful motivator and catalyst for learning when provided in a supportive, learning-rich context; a strong, direct connection to the local labor market and its employers is critical; work preparation strategies must take into account young people's developmental needs; strong relationships with competent, caring adults are essential; impacts of program design on different population subgroups vary greatly; quality of implementation matters greatly; and results take time. Priorities for the future are strategies to address the economic and social landscape of opportunity, improve the design and delivery of skill-related interventions, and improve community-level partnerships. (Contains 208 references.) (YLB)