Helping young people prepare to engage in work and life as productive adults is a central challenge for any society. Yet, many young people in the United States find that the path from education to employment and economic security in adulthood is poorly marked or inaccessible. As a result, those from low-income and less educated families have lower rates of high school graduation, college enrollment, and college completion. Using an advanced methodology and longitudinal data, this report examines two main questions: (1) the quality of jobs (as measured by wages, benefits, hours, and job satisfaction) held by 29-year-olds who experienced disadvantage in adolescence; and (2) the particular adolescent and young adulthood employment, education, and training experiences of people from disadvantaged backgrounds that are associated with higher quality jobs at age 29. Among those who were disadvantaged as adolescents, the vast majority (79 percent) are employed at age 29. Among those workers, 38 percent have high-quality jobs as measured by our job quality index. Their counterparts--29-year-olds from non-disadvantaged backgrounds--fare better: 90 percent are employed, and 48 percent of those have high-quality jobs. This report identifies a number of factors that shape job quality among 29-year-olds from disadvantaged backgrounds: (1) Work-based learning incorporating positive relationships with adults; (2) Earlier experiences in the labor market; and (3) Educational credentials and training. This report provides four recommendations to improve the employment prospects of young people growing up in disadvantaged households: (1) Expand work-based learning within high school career and technical education; (2) Increase completion rates of post-secondary degrees, with an explicit focus on quality and equity; (3) Improve on-ramps to employment for teens and young adults; and (4) Promote further research and action on the role of positive relationships in employment and training programs for youth and young adults. [This document was prepared for the Metropolitan Policy Program at Brookings. Additional funding for this report was provided by the Metropolitan Council.]