In our continuing discussion of the sideways world actually coming first in real after life time to that of the island world, how does this affect the central character of Jack?
In the sideways after life, Jack is still a brilliant surgeon who wants to fix every patient, including those who need "a miracle." Jack is divorced from a fellow doctor, Juliet. He lives with teenage but estranged son, David. It seems like the typical suburban LA family life.
He still has relationship issues to work out. He has problems with his father. He has mirrored those issues with his own son, David, by having his professional duties take precedence over family matters.
When Jack landed on the island, what issues did he have to work out? We must down play his alleged lack of leadership (to make the life and death decisions) because as a trauma surgeon, he led his teams through those decisions on a daily basis. The main focus of his attention beyond mere survival was finding a final connection with his dad because Ghost Christian haunted him. One could think that the island's series of tests was to put Jack into Christian's shoes, but that really is not the case.
In the island world, Jack has similar but more serious problems. Yes, he is divorced from Sarah but he has no children. She has quickly moved on to a new husband to start her family. Jack is angry about being alone and depressed; he turns to alcohol and drugs which ruins his professional standing and draws him close to suicide. Clearly, Jack is worst off in the island world than in the sideways world.
Are the island demons Jack's subconscious feelings that need to be conquered and tamed? They seem fairly tamed in the sideways world so there must be a different answer.
What Jack lacks in both worlds is a true soul mate. Someone has stubborn, argumentative and loyal that he is. But does the island world give him an opportunity to work out his relationship issues with women to the point where he finds bliss? This is debatable. We have various women thrown in Jack's romantic path, including Juliet, Kate, Achara, and Sarah. None of them ended well. Even after defeating MIB, Kate did not stay by mortally wounded Jack. No, Kate left with Sawyer to find the plane to leave the island and Jack behind. That was Kate's choice.
If the island was a proving ground for something missing in Jack's after life soul, what was it?
It is not as clear cut as Juliet and Sawyer's awakening and rekindling of their island romance.
It is less black and white of the polarization of Ben's relationships with Danielle in the island versus sideways worlds.
Was it all the personal sacrifices Jack made on or to the Island that led him to a revelation about himself? No lesson was learned because Jack sacrificed himself like he sacrificed himself to save others in his real life. Jack's general personality did not change between worlds.
Was it as simple as finding out people do get "second chances" and things are not "fixed" in time or space? This would explain his rocky relationship with Kate, its on and off head butting on and off the island, to the non-contact with her until the very end at the church. Jack had no relationship with Kate in the sideways world but connected with her for the next level of the after life. Kate always said she'd have Jack's back. And in the final sense, she would take him back, this time forever.
But the one concern with Sideways Jack is his love and devotion to his son, David. But since we know the sideways world is inhabited by dead souls, who was David? Was he a figment of Jack and Juliet's imaginations? He does not fit into a piece to be worked out in the island realm. He does not figure into the finale either. Jack never asks Christian "where is David?" There is no rule against "moving on" with your children (Claire and Aaron; Christian with his two children). So David is an anomaly in the sideways time is first theory. If Jack's real desire was to a have a normal, stable family life with a wife and child, then that dream is never fulfilled. However, if Jack's dream was to be released from responsibility and commitment (themes of the island world), then death would be the only answer, i.e. the sideways world. Jack's meeting his dead father "in person" awoke him to the notion that his life was over. But at that moment, he did not know who was in the church except Kate.
What did the people in the church give Jack during his island time that he failed to find in the sideways world? Friendship.
Friendship is the emotions or conduct of friends; a state of mutual trust and support.
The island proving ground did give Jack the opportunity, in a non-medical setting like a hospital, to learn to trust and support other people. To seek judgment, opinions, and options from other people. To argue, make decisions, and make mistakes. And through all those arguments, decisions, mistakes and events, people did not turn their backs to him. Jack learned how to make lasting friendships. And in many respects, it was a mutual experiment for characters like Locke and Boone. The bonds of friendship is what Jack's soul was missing in its real life.