In Tim Jacobs' "The Fight: Considering David Foster Wallace Considering You" the author argues that Wallace constantly kept the reader in his mind as he wrote. While his writing may provide challenges, they also demonstrated his commitment to the reader. Or rather to the avid, educated, enthusiastic reader. Those that looked to the written word for a connection to the harsh reality of their everday lives. Despite the daunting volume of Infinite Jest, Wallace understood that the reader needed to trust the author would not disappoint them. Jacob's writes that Wallace "fretted over whether his work had rewarding enough payoffs for the commitment and linguistic effort you had to put into reading him." Wallace knew that a dictionary would need to be in arm's reach at all times, while deciphering his work. However, at the same time, he did not want the experience to be about him. If it did then the author would fall into the same solipisistic traps that Hal does in Infinite Jest. To avoid this, he made his voice present in his fictional works.
For example, in Infinite Jest the reader is aware at times that the author is speaking directly to them. His use of footnotes is one obvious way he "opens up the fourth wall to undisguised mediation." In this way he places himself on equal ground with the reader, as if he is going through the experience of the novel with you. This connection gives the reader the impression that they are not alone with the novel. Wallace, or the narrator, is with them. Jacob's description of reading contemporary fiction as a lonely experience and the theme of loneliness in Infinite Jest seem to parallel. In fact, Jacobs points out that the characters of the novel "understand that the reader sees the text" when he remembers a sign he saw as a kid:
LIFE IS LIKE TENNIS
THOSE WHO SERVE
BEST USUALLY WIN
Hal recalls the sign "with the letters spaced far out like that, (952)" This kind of meta/direct address would stand out in another novel, but David Foster Wallace has cultivated such a understanding with the reader that it is accepted without question.
There is no doubt that Wallace considers the reader when he is writing. However, Tim Jacob's clear affection for Wallace colors his ability to write anything objective about him. While he does provide some insight into Wallace as a reader's writer he seems to consider Wallace to be some sort of messiah figure. We can agree that David Foster Wallace was a brilliant man, but it is quite a stretch to believe he intended for the reader to find the meaning of life in his works.

Jacobs, Tim. "The Fight: Considering David Foster Wallace Considering You". Rain Taxi Review of Books. Online Edition, Part Two. Winter 2009

Wallace, David Foster. Infinite Jest. New York: Back Bay Books, 1996.