This study compares a sample of approximately 44 first year college students in 2005 and 2015 on Long Island, New York, in their technology preparedness and self-directed instruction. The researchers used a survey instrument including demographic information focused upon students' preparation for classroom technology in high school and college. First, the study compared the extent to which students use self-directed instruction relative to proficiency in technology in 2005 and 2015. Second, the study examined the technology preparedness in high schools and colleges. Third, the study compared the difference in technology preparedness in high school and college between students in 2005 and 2015.