This paper shows that while high school dropouts fare far worse on average than otherwise similar high school completers in early adulthood outcomes such as success in the labor market and future criminal activity, there are important differences within this group of dropouts. Notably, those who feel "pulled" out of school (i.e, they say they dropped out of school to work or take care of family) do similarly with respect to labor market and criminal outcomes in their early twenties to individuals with similar pre-dropout characteristics who complete high school. It is only those who feel they are more "pushed" out of school (i.e, they say they drop out for other reasons including expulsion, poor grades, moving, and not liking school) who do substantially worse than otherwise similar high school completers. These results suggest that any detrimental impacts from dropping out of school arise primarily when the drop out does not have a plan for how to use his time after dropping out.