In study after study, people lying on their deathbeds overwhelmingly say they regret five things at their end of their life: 1. Not living a life of authenticity 2. Working too hard at the expense of their relationships 3. Not having the courage to express their feelings 4. Not staying in touch with friends. 5. Not letting themselves be happier. For leaders, it's not any different. This course unpacks each of these "regrets" with readings, exercises, meditation, deep listening, skill development and leadership theory, examining historical and contemporary answers to the question of what really matters in life, and providing the space for students to grapple with the question themselves.