An Academic Scholarship Program for engineering and computer science students is one form of a retention program. The authors have taught Academic Scholarship programs with an emphasis on women and underrepresented minority students for a combined 14 years. The students in these Academic Scholarship Programs are required to attend workshops and do assignments as part of the program. The assignments are designed to help the students be retained well, to consider graduate school, and to plan for their future. As a component of an Academic Scholarship Program, students may be given an assignment to detail their plans for the next 10 years or the first 10 years after they earn their Bachelor's degree. This "thinking ahead" can include a serious planning of the rest of the courses needed for a Bachelor's degree and what the student intends to do upon completion of the Bachelor's degree in engineering or computer science. The assignment parameters can vary greatly. The students can be asked to simply give an outline of what they plan to do for the first 10 years after they graduate. The students can also be asked for a detailed personal career statement that could be more than 5 pages. This paper will consider the "Ten Year Plan" assignment. In particular, we are concerned with the students' plans to attend graduate school. The authors analyze two models. The purpose of the paper is to give insights based on our experiences on making this type of exercise a meaningful one for faculty and students.