This study of fifteen first generation American college freshmen documents their initial semester with a focus on factors and dispositions contributing to eventual success or failure. Students were identified prior to campus arrival, allowing for immediate and real-time data collection as they were experiencing the beginning of their college careers. Key factors identified and explored include the importance of active help-seeking, effective management of unstructured time, the dangers of underestimating academic rigor, and the crucial nature of the first two weeks. Suggestions for how the findings may be of practical use, as well as further research implications, are included.