The purpose of this project is to understand how wearable technology can improve a person's practice of self-tracking, or monitoring one's data. Self-tracking is regularly recording information about one's different life patterns (such as diet, activities, or sleep). Some technology that helps users record personal data are seen today as devices (FitBit, Smart Watches) or as applications (MyFitnessPal). Data is collected for the user to observe certain habits that he/she would like to improve upon. Their personal data that is collected and this helps keep the person self-tracking. This data can be converted to show personal behavioral patterns which a person analyzes so that they can make changes that lead to a healthier lifestyle. People self-track in order to analyze their behavior patterns, so that they can make changes to those patterns that lead to a healthier lifestyle. However, some people are not motivated to continue self-tracking, or use their data to make positive behavioral changes. To better understand this problem, we are conducting four co-design sessions with four users who have shown varying levels of self-tracking. Sessions' activities included: storyboarding, reviewing existing user interfaces, generating feedback on prototypes and discussion into thoughts and feelings about the prototype and self-tracking in general. Current findings highlight the importance of customization and simplicity within the application. We are developing an Apple Watch prototype application for self-tracking that incorporates features tailored to those needs in order to better motivate users to track and improve their well-being. Our main goal is to gain a better understanding of our participants and their need and usage with self-tracking. More information can be found on our website at ani6gup.me/CareTrack.