A vast body of research finds an association between missteps taken during the teen years (such as motherhood or dropping out of high school) and poor economic and educational outcomes. However, youth who take major missteps as teens often have subsequent success in school or the labor market. This paper attempts to draw lessons from youth who appear headed for a poor start in life, yet manage to have a positive economic or educational outcome by their early 20s. Using National Educational Longitudinal Survey (NELS), we provide one of the first longitudinal analyses of well-being for teen mothers and high school dropouts that includes a nationally-representative population of Hispanic and Asian youth. In general, the predictors of positive outcomes are similar for those with high probabilities of poor starts as for the general population. A few high-school-age behaviors and community measures have additional associations with positive outcomes for likely poor starters. However, these correlates do not appear for all groups of likely poor starters, and they are not always in the expected direction.