The unrelenting high unemployment/underemployment rates following the 2008 recession have become a possibly structural problem for the U.S. economy. Today’s jobseekers face many difficulties, some of which may be better addressed by understanding the mental models held by jobseekers towards being unemployed and underemployed. Rule developing experimentation identified three types of mental models towards unemployment: “I’m out of date”, “I still got it”, and “I need to adapt”. Each mental model carries with it suggestions about what customized courses of action policymakers can recommend for the individual. This paper discusses the findings and implications for policymakers and unemployment/underemployed service providers.