Task management is hardly, if ever, a fun and exciting process. Part of the difficulty of staying motivated towards your goals is the constant stress of failure due to unrealistic deadlines or unnecessary time restraints. Our project aims to help end the stress of task management with a new type of app that motivates users based on achievements and provides a space dedicated to note taking and task tracking. Some of the key features of this app will be: Haptic Feedback Note Taking Capabilities User Score Push / Pop Effects These features, while not entirely original in themselves, are well-documented and are currently in use in other types of applications. Existing examples can help to inspire our design and make implementation an easily achievable goal. OpenKeep is an application used for tracking the tasks of an individual. This application seeks to provide tools and motivation to users as they progress towards task completion. Unlike the wide variety of currently available organizational apps, OpenKeep is built around the idea that individuals can be encouraged to work on their tasks without the need for strict, time-based deadlines. Since this app is designed to increase productivity and motivation, an additional feature to this app is a self-advice interface. No more bookmarking websites and keeping forgotten productivity advice from blogs or websites. OpenKeep’s self-advice interface allows the user to consolidate all useful productivity information collected from websites/blogs and reminds them at set times. This paper provides the results of our empirical and analytical evaluations of our revised user interface prototype. The goal of these evaluations is to optimize user experience in OpenKeep.