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In this article, we explore a program designed to engage high school and college students with learning disabilities (LD) in conversations about their hopes, expectations, and fears for the future. We explore the mindset of students by focusing on their self-identified passions for life and sense of strengths and limitations. We found that males and females differed in goals related to Academics, Work Ethic, Degree Specific Statements, and Money and Finances. For example, females emphasized “Academic Goals” more frequently than males and focused on topics such as GPA and work ethic in school. However, males made more “Degree Specific Statements” than females, more often emphasizing the desire to be financially stable or have a career with a large income. These differences suggest that college transition staff may want to focus on goals identified by male and female students with LD as a way to be more responsive to student self-identified goals.