In Into the Wild, what was Chris McCandless's biggest challenge?

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On a literal level, Chris McCandless's biggest challenge was his final one: fronting the Alaskan wilderness alone, where he met unexpected hardships and had to cope with the inevitability of death at early age.

On a more profound level, McCandless's biggest challenges, as he well knew, were his own inner...

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On a literal level, Chris McCandless's biggest challenge was his final one: fronting the Alaskan wilderness alone, where he met unexpected hardships and had to cope with the inevitability of death at early age.

On a more profound level, McCandless's biggest challenges, as he well knew, were his own inner demons. He went to the Alaskan wilderness to challenge them, and from what we know from the writings he left behind, he won the inner battle even as he lost the outer fight for physical survival.

In journals he kept in the last weeks of his life, he recorded a change of consciousness. For example, after his failure with the moose he shot, he came to grips with himself and his disappointment and was able to write,

I am reborn. This is my dawn. Real life has just begun.

On July 2, about six weeks before his death, after reading Tolstoy, McCandless wrote that the only happiness in life is living for others. He showed he was on a path to contentment and inner peace when he stated the following:

I have lived through much, and now I think I have found what is needed for happiness. A quiet secluded life in the country, with the possibility of being useful to people to whom it is easy to do good, and who are not accustomed to have it done to them; then work which one hopes may be of some use; then rest, nature, books, music, love for one’s neighbor—such is my idea of happiness.

And then, on top of all that, you for a mate, and children, perhaps—what more can the heart of a man desire?

As he was dying alone in the wilderness, McCandless penned a final note, writing in all caps:

I HAVE HAD A HAPPY LIFE AND THANK THE LORD. GOODBYE AND MAY GOD BLESS ALL!

Chris's acceptance of his death and his ability to find happiness and think about blessing others in the worst possible circumstances, as a young man on the brink of adult life, show how he had matured inwardly. Much of his anger seems to have peeled away in his final days as he faced severe challenges.

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On a pragmatic level, Chris Mccandless struggled with gaining the skills to survive on his own. His determination to live alone and far from the world of capitalism and greed that he abhorred was a way of rejecting his own participation in that system. But by avoiding having a community, Chris made certain he would have no one to turn to when he needed help. In the end, it was solitude that killed him, not only because having people around could have helped Chris avoid starvation but because other people could have helped him see he was being naive and stubbornly idealistic.

Despite being well read and an autodidact to some extent, Chris failed to educate himself about what it really meant to live off the land. He was blithely unaware of his own ability to survive without assistance. Without learning more self-sufficient means of feeding himself, like identifying edible plants or storing hunted meat for winter, he guaranteed he would starve in the wilderness.

Chris's stubbornness was perhaps his biggest challenge in this regard. He was so determined to leave his old life behind that he was blind to the fact that he had actually been very reliant on what money and privilege did for him: it kept a roof over his head and his belly full. By refusing to admit defeat—or that he was vulnerable when he was alone—he was also setting himself up for failure.

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Chris McCandless faced an identity crisis in which he failed to balance realistic and romantic views of himself.

Ultimately, he convinced himself that his book-hero persona Alexander Supertramp could survive the Alaskan outback with a small caliber rifle and a ten pound bag of rice.  This act of hubris was a result of mistaking the realism of Jack London and Leo Tolstoy as Romantic cult pulp.  Rather than confronting his father's past and his own role in the materialistic American culture at large, McCandless isolated himself in nature to spite mankind.  Ironically, he failed to realize how profoundly he impacted even the unlikeliest of strangers (in Ron Franz).  His epiphany of "happiness is only real when shared" was realized in the throes of starvation.

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