Wearable technologies designed to deliver benefits to health and well-being through the use of digital applications are becoming increasingly ubiquitous. This article focuses on the use of wearable technologies which track user lifestyle behaviors and seek to provide tools for better personal health management. It provides an evidence of general positive health outcomes from previous research and provides a detailed analysis of the functionalities and strategic approaches of three different wearable devices which have been used continuously and simultaneously by the lead author for over 18 months. Based on the experience of long-term use of these devices, the article draws some conclusions about their usage and future development strategies.