The author spoke with four college students in September of their freshman year, along with their parents, about their journey to becoming college freshmen. Three students graduated from New York State public high schools, and one graduated from a New York State private high school. Three of the students were the first child in the family to attend college; one was the second. Both parents of all four students earned at least a bachelor’s degree. Several themes emerged from the conversations worthy of further exploration. The first is how the decision to attend college emerged. The second is the investment the college process demands. The structure of and embedded opportunities in the school program significantly impacted students and families. Finally, the common and unique influential factors and individual decision-making processes surfaced.