Calling It Quits (2008)

Dante Milestone, a world-weary baby-boomer, is not happy. His struggles with everyday life, his past, even the question of 'the existence of a higher power', have led him to evaluate his own life. An assessment, that ultimately drives him to leave work and success behind, and set out on a quest in search of his happiness. But Dante soon learns that it's not that simple, for after a series of painfully humorous attempts fail to provide an answer, Dante sinks even deeper. It is not until he encounters Cynthia, a spiritual guide of sorts, that he uncovers the underlying truth and finally arrives at an answer that surprises even him.