The Family Man is a contemporary twist on a timeless tale. Jack Campbell is given the chance to see how life would be different had he chosen a different path. This glimpse at a drastically different life may convince him that the life he is living may not be the life that he needs. Jack is a wealthy, greedy, arrogant Wall Street businessman. He is single; his only love being money and his possessions. On Christmas Eve, after receiving a phone message from his ex-girlfriend Kate, Jack heads out of the office. He stops at a convenience store where a disgruntled man named Cash holds up the store clerk, then turns the gun on Jack. Concerned for his own life, Jack agrees to help the gunman.
Christmas morning, Jack wakes up to a completely different life. He and Kate are now married with two kids. Confused and scared, he rushes to his office. There he finds out no one knows him. However, he does run into Cash. Cash explains that Jack is being shown an alternate life to teach him a lesson which he has to figure out for himself.
A few days in this life--one he would have had if he chose love over career--makes Jack realize what he should truly value. Obviously this is the lesson Jack needed to figure out and he has the opportunity to run into Cash again. After begging to stay in this life, Cash reluctantly reveals he cannot. With this realization, Jack is jolted back to Christmas Day and his old unfulfilled life.
Desperately he tracks down Kate, who also decided to focus on her career after their break-up. She is a lawyer and moving to Paris. He describes to her the life and family they could have. She agrees to meet him for coffee--leaving it up to the viewer to decide if they find this life together.