It can't be proved that Chris had a specific inferiority complex, but it can't be denied that he felt the need to constantly prove himself against nature. He seemed to feel that proving himself against society was a meaningless gesture; everyone around him was also working to prove themselves against society, and he saw that as a trap, leading to an endless cycle of work and failure. Instead, he wanted to prove himself against a constant, nature, something that humanity can affect but ultimately never change. By working through his personal issues and personal growth via isolation, Chris wanted to become a stronger person with a more complex outlook, not the office drone that he saw in most of society. A comment by Wayne Westerberg may shed some light on Chris's feelings:
"I got the impression that this Alaska escapade was going to be his last big adventure," Westerberg offers, "and that he wanted to settle down some. He said he wasgoing to write a book about his travels."
(Krakauer, Into the Wild, Amazon.com)
It seems that the journey to Alaska was in itself the destination, the experience of living in isolation and surviving off the land. Chris may have felt inferior to his heroes, like Thoreau and London, who experienced the world in a harsher time compared to his relative comfort. Instead of sitting back and letting himself exist in stagnation, as he saw others as doing, Chris intended to create a base of experiences for himself on which to create his later life. If Chris felt inferior to anything, it was to the high expectations that he placed on himself; most of the people he met thought very highly of Chris, and said so often.
That is an interesting question because Chris had a need to be socially isolated from others. I am not sure what had led to make him feel inferior but I believe that he felt inferior in the sense that he was actually embarrassed by his parent’s life and his father's money.
Chris had a strong need to be alone, but he also had o keep proving himself to himself. I see that some of his trips and his reluctance to bring appropriate provisions were his desire to be like Walden. However he fell short of his own success. Chris wanted to be able to live off of the land and to need no one or anything. He wanted to be totally independent of man made things. He was very intelligent but I believe he felt that he had been dealt a raw hand at having the gifts that he was born into.
Chris also suffered trauma over his father’s cheating on his mother.
His final goal was to be able to know that he had lived in the Alaskan wild. He tried to full fill his goal but died in the process.