Throughout Alex's/Christopher's journey in Into the Wild the reader commiserates to a point with the main character. We have all felt angst and confusion toward things, especially once we find ourselves in those crossover moments in life when we have to go from being adolescents to young adults in a matter of months. While Christopher felt that his task was to isolate himself and learn to understand life hands-on in the wilderness, it is clear that the boy lacks the experience to realize that he is quite misguided as a whole.
This being said, fast forward to chapter 18, the day of July 2 of 1992, when he has read two edifying books: One is Leo Tolstoy’s The Death of Ivan Ilyich where we see hints that he may have finally gotten a clue about life. We know that he had been doing a lot of reading and analyzing.
He reads Tolstoy's The Death of Ivan Ilyich, which is the story of a man who, similarly to McCandless, realizes the shallowness of his relationships with others shortly before dying. McCandless also read Doctor Zhivago, whose eponymous main character is constantly divided between his emotions for two women. It is in this book that McCandless enters the observation:
"HAPPINESS ONLY REAL WHEN SHARED."
While McCandless never even attempts to say good-bye to his family, the emotion of that statement is quite shocking since McCandless’s main issue is his inability to connect with others. Therefore, while the statement is not directed at his family, it certainly must refer to them because, at that time, he would have only had them with whom to share whatever happiness he would have had.