This case describes the thoughts and reflections of five MBA alumni on their way back to their alma mater for a 20-year reunion event. As invited speakers, they will advise the upcoming graduating class on what to expect after graduation. The case provides a brief background on the career trajectories and family circumstances of each of the five protagonists as well as their personal reflections on their accomplishments and their regrets. The case is an excellent starting point for thought and discussion on the goals and motivations of MBA students, and what they expected to achieve and how they would measure success over the medium to long term. This case would be appropriate either alone or in conjunction with the technical note “Are You Ready? Devising a Personal Strategy for Life after Business School” (UVA-S-0342) as an effective reinforcement exercise.