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Contemporary adolescents in the United States have especially ambitious educational goals, as over 4 out of 5 high school seniors aspire to earn at least a 4-year college degree and over half expect to attend graduate or professional school. Yet, teenagers today face an expanding and diversifying system of higher education, rising tuition rates coupled with a relatively high risk of college attrition, a precarious job market characterized by weak linkages between schools and employers, and debates about whether a college degree is still worth it. In this context, we consider whether uncertainty in educational expectations among contemporary adolescents is a strategic response to an increasingly uncertain and individualized transition from school to work, fostering college matriculation and reducing the likelihood of attrition. Using data from four waves of the High School Longitudinal Study of 2009 (HSLS:09), the present study seeks to investigate whether uncertainty in educational expectations is associated with college matriculation, college dropout, and employment in early adulthood. Preliminary results indicate that about 9% of 11th graders were uncertain about their future educational attainment, and that youth who expected to earn 4-year degrees or more were 2 to 3 times more likely than uncertain youth to attend college in the three years following the scheduled date of high school graduation. Our next step is to assess whether uncertain educational expectations increase the risk of college attrition (among those who do attend college) or the risk of NEET status (i.e., not in education, employment, or training).