Employment status in high school has been shown to have a negative relationship with measures of academic achievement which some researchers have attributed to student characteristics such as demographics and socioeconomic status. The current study investigated differences in the demographic and socioeconomic characteristics of "working learners" (high school students working 15 hours or more a week) and non-working learners, and how working learner status is related to a measure of postsecondary readiness as well as career sureness using self-reported data from a national assessment of educational achievement (n = 366,528). High school working learners were more likely to be of lower SES and have lower postsecondary readiness scores compared to non-working learners. Working learners were also more likely to expect to work intensely while in college to be sure of their career plans compared to non-working learners.