Planning and preparing for life after high school is a central developmental task of American adolescents, and may be even more critical for low-income youth who are less likely to attend a four year college. This study investigates factors that led to the effects of the New Hope Project, a work-based, anti-poverty program directed at parents on youths' career-related thoughts and planning. The New Hope project was implemented in Milwaukee, WI, during the mid-1990s. 745 families participated (52 % male children; 56 % African American; 30 % Latino, and 15 % White non-Hispanic) and half were randomly selected to receive New Hope benefits, which included earnings supplements, job search assistance, and child and health care subsidies for 3 years. Importantly, effects on youths' future orientation were found 8 years after the program began (5 years after benefits ended). The present study investigates what factors sustained these positive impacts over time. Results indicate that parental perceptions of reading performance mediate the effects of New Hope on youths' cynicism about work. Additionally, parental perceptions of reading performance and youths' educational expectations mediate the effects of New Hope on boys' pessimism about future employment. These findings highlight the importance of youths' educational development to their career-related thoughts and planning.