Every day, academic leaders make decisions about what kinds of programming college first-year students will find attractive and engaging. Many colleges’ ideas, however, fail to connect to student interest and experience. Part of the reason for this disconnect is generational. The staff and administrators planning these programs are at least a decade and a few academic degrees removed from the people they are planning for. While administrators and staff in academic and student affairs can use surveys and focus groups to understand student needs and inclinations, these guesses can be off the mark and, more importantly, lead them to miss real opportunities for first-year student programming.