Research provides ample evidence of the impact web page design has on comprehension; and that Generation Y users are impatient and dislike reading text. Yet there has been little research that focuses on content, in particular to examine the impact of text simplification on younger users’ processing of textual information. To address this need, we report the initial steps of a larger research effort that focuses on developing a set of guidelines for designing simple and effective text passages. Specifically, we compiled a set of existing plain language rules and tested its effectiveness of conveying information to Generation Y users. The results suggest the compiled set of rules can serve as an appropriate tool for designing textual passages to reduce cognitive effort and improve readability of textual content for Generation Y users. Also, the results show that eye tracking serves as an excellent objective measurement for examining the effectiveness of text simplification.