Since the advent of technology and the Internet, adolescents and young adults have discovered instant messaging (IM), a powerful and useful social networking vehicle for communication. Although studies identified a burgeoning growth of IM use among the millennial population, limited research exists regarding the effects of IM use on self-esteem, leadership, and school performance. The purpose of the study was to explore the lived experiences and perceptions of using IM by millennial students who were self-described high-end IM users. The intent of the qualitative phenomenological study was to determine how IM, as a tool of communication, affects the self-esteem, leadership, and school performance of high school students. Interview results from 20 high school graduates between the ages of 18 and 21 who were self-described high-end users of IM are as follows: (a) students reported IM was an enjoyable, convenient, time efficient, cost effective, and easy way to communicate with their friends and classmates; (b) in regard to self-esteem, many students engaged in respectful interaction that deepened relationships and encouraged a sense of belonging, whereas several students used IM to gossip and fight with one another, causing hurt feelings; (c) in regard to school performance, although some students reported IM distracted and delayed them from doing homework, many students discovered IM was a useful tool for seeking assistance from one another with schoolwork; and (d) in regard to leadership, whereas some students reported incidences of hurtful and dishonest behavior on IM, many students described increased confidence and assertiveness. The findings from the study add to the body of literature on the effects of IM on high school students as described from their lived experiences and perceptions of IM use. The study includes a discussion of future research in social networking and technology use in schools.