Twenty-six work-bound, college-able, rural high school seniors were interviewed regarding their post-high-school aspirations, their views of the transitions associated with leaving high school, and the processes by which they came to think of themselves as work-bound. One of several emergent themes is presented: students' perspectives of the real world and how these perspectives have influenced their post-high school aspirations. Recommendations are made for school personnel, particularly counselors, to address high school students' career and lifestyle development need from a contextual perspective.