Helping young people prepare to engage in work and life as productive adults is a central challenge for any society. In theory, the path to employment providing financial security in adulthood is simple: finish high school, enroll in and complete college or training that is affordable and a good fit, gain some work experience along the way, and launch a career. But given that 17 per cent of young adults ages 18 to 24 are out of work in mid to large cities in the U.S., totaling 2.3 million young people, this path does not appear to work equally well for all, particularly in light of the effects of the Great Recession and the declining rates of employment among teens and young adults since about 2000. Though millions of young Americans are out of work, they are not monolithic. We used cluster analysis to segment out-of-work young adults into five groups, represented by personas, likely to benefit from similar types of employment and educational assistance. We grouped young people together based on similarities in their work history, educational attainment, school enrollment, English language proficiency, family status, and other characteristics. Lastly, the report provides recommendations for state, local, civic, and institutional leaders to help all young people successfully navigate the transition into the labor market.