Getting the sufficient amount of quality sleep is a key aspect of good health along with a healthy diet and regular exercise. Despite its importance, sleep has been considerably underexplored in the area of human-computer interaction. In this proposal, I describe my research in understanding the need to help improve people's sleep habits and creating a persuasive sleep application to help them achieve their sleep-related goals. The persuasive sleep application involves self-monitoring and feedback features to help people be aware of their sleep habits. My dissertation research investigates a design of a self-monitoring system focusing on how information is presented as a persuasive means accounting for user emotions in the context of receiving concerning health news.