Growing numbers of students are entering college without the necessary skills to be successful in post-secondary education. Habits of learning and dispositions of learning may not be at the level needed for success in college. The purpose of this study was to identify the habits of learning and the dispositions of learning of sixth-grade students at an elementary school and community college freshmen. This study was a qualitative approach that explored students’ perceptions, experiences, and beliefs about their learning habits and dispositions. While there was not much difference in the overall responses of the 2 groups of students on the habits of learning survey, males showed the greatest gains in the area of preparation for assignments and expectations, while female students did not respond with many changes, yet on the dispositions of learning survey gains for both male and female students were scored in many areas especially resourcefulness and goal-setting with major gains for male students in cooperation. Results from this study revealed there was a considerable gap between how students scored themselves on the habits of learning survey, which indicated many struggled in this area as compared to the dispositions of learning survey which received more positive responses. Some of the trends that were found include that motivation decreased from sixth grade students to college freshmen, more changes was noted in male students than female students, and college freshman gained in almost every area in the dispositions of learning survey. Implications from this study showed a need for teachers to focus on habits and dispositions of learning to improve the students’ own awarenesses of how they learn throughout the secondary school years, especially considering how much positive attitudes can influence learning in school.