We investigate the motivation and means through which individuals expand their skill-set by analyzing a survey of applicants from the Facebook Jobs product . Individuals who report being influenced by their networks or local economy are over 29% more likely to have a postsecondary degree, but peer effects still exist among those who do not acknowledge such influences . Users with postsecondary degrees are more likely to upskill in general, by continuing coursework or applying to higher-skill jobs, though the latter is more common among users across all education backgrounds . These findings indicate that policies aimed at connecting individuals with different educational backgrounds can encourage upskilling . Policies that encourage users to enroll in coursework may not be as effective among individuals with a high school degree or less . Instead, connecting such individuals to opportunities that value skills acquired outside of a formal education, and allow for on-the-job training, may be more effective.