Wearable activity trackers have been consistently used for tracking, measuring, and even improving people’s physical health and well-being. A study was conducted to investigate the user experiences while wearing and while not wearing the trackers (for whatever reason). The emphasis was placed on the psychological aspect of wearing the trackers. The results have revealed a predominantly positive experience for the people who were wearing the device, whereas, as expected, the negative outcome was associated with situations when people were not wearing their activity trackers. The conclusion is that people consider the wearable activity trackers a legitimate and a reliable method for improving the quality of their lives, physically and psychologically.