PESSIMISM

No pessimist ever discovered the secrets of the stars, or sailed to an uncharted land, or opened a new heaven to the human spirit. — Helen Keller

Pessimism is a a tendency to see the worst aspect of things or believe that the worst will happen; a lack of hope or confidence in the future, for example, a dispute could cast an air of deep pessimism over the future of something.  In philosophy, it is a belief that this world is as bad as it could be or that evil will ultimately prevail over good.

There was a lot of pessimism in LOST, both on the surface, in the characters and in the final meaning of the series.

Hurley was a pessimist. He believed that the worst was going to happen to him; he was cursed and people around him would get hurt. From his father leaving him as a boy, to the deadly porch collapse that sent him to the mental institution, to the learning of the Numbers which cursed him with wealth and resulting bad luck and misfortune.

That was the island view of Hurley. The sideways world had Hurley as a more confident man of the community. His only problem was that he was lonely; he was too shy around women. There was a feeling that women would only be interested him for his money, and not the real Hugo Reyes. So in that respect, he was a man trapped on his own relationship island.

Kate was also a pessimist. Unlike Hurley who sat around for something bad to happen to him, Kate tried to run away from the worst aspects of her personality and actions. Kate lacked any hope or vision for her future. She doomed herself at an early age to be a runaway. She let the excitement of evil entice her to do bad things. She never felt that she could change, especially after time and time again, hurting the people she cared about.

That view of Kate carried forward into the sideways world. She was not confident that she would ever have a bright future. She was going to jail for her crimes. She would amount to nothing in the grand scheme of things. She would never find happiness. Her fate was sealed at an early age.

Certain aspects of Jack's life were based on internal pessimism. He inability to get his father's approval led Jack to make huge missteps in his life. He saw the worst aspects of himself translate into relationship issues with his wife, Sarah. He saw the worst aspects of his father translate into alcoholism, addiction and depression after he changed his story on his father's negligent surgery. The lack of his father's acknowledgement of his own abilities led Jack to the darkness of a bitter, lonely existence.

In an odd twist, those characters who had the worst of it - - - the poorest, the weakest, and the most disillusioned  - - -  found the secrets of the stars, sailed into uncharted waters, and opened a new heaven for their human spirit. For no apparent reason, Desmond became the main characters guardian gatekeeper from the island world to the sideways heaven. Desmond apparently became supernatural after he turned the fail safe key. Part of him made it beyond the island and triggered a response in the sideways world. He just needed someone less pessimistic than himself to open the gate to allow the sideways characters to awaken. 

Charlie was the key to unlock Desmond's gate. It was Charlie's crazy optimism bouncing off his dark self loathing before Daniel's special concert that brought full knowledge of the situation to Desmond's spirit.  He realized that he could bring all the island friends and associates "back" if he could somehow put them into situations that could create a memory bridge to the past. Strong emotional pulls would pull the characters through to the end. In an ironic twist, it was Charlie who was the last islander to awake in the sideways world after he witnessed Aaron's birth.

Desmond's sole outlook in life was to win Penny back from his stupid lack of commitment and his self-loathing about being able to cope in a middle class world of work and responsibility. He decided that he had to overcome Widmore's oppressive personality and will to gain favor in Penny's soul. So Desmond took off to prove himself to Widmore and therefore Penny by solo sailing across the Pacific. He would use the stars to navigate. He would be in uncharted waters. He would place himself in danger. He would put everything on the line to win Penny. He would prevail or he would perish. He was optimistic that he would win Penny back. 

Whether this was a self-wager with the devil with the prize being Penny is a question of debate. Some could consider Desmond's plan as being asinine and self-destructive. The excuse was to win Penny back, but in reality it was a means of leaving her forever as he would never survive the perils at sea. It was a suicide mission to avoid his fears of commitment and settling down. In one respect, Desmond had to die in order to get Penny back in the sideways world. If the island realm was a grand test of Desmond's love and commitment, it could only manifest itself when he awakened in the sideways world and reclaimed Penny and her feelings/memories of him at the concert.

It was like the sideways purgatory was a place where souls milled about stewing about the regrets of their lives. Those who could not fix those regrets were doomed to stay in purgatory. But those who decided to fashion a "test" to bring their past decisions into the present of the after life would be rewarded in the end. The test was the island, a proving ground for pessimists to erase their past regrets.