People with cognitive impairments are frequently affected in their time-processing ability (TPA). This lack of timely orientation makes them dependent on others to allot their time to tasks throughout the day. To enable affected adolescents to understand daily schedules, as well as recognising and attending appointments and routines more independently, we developed a digital watch face that highlights activity symbols instead of numbers. A four-day ABAB test with six adolescents in an assisted living facility revealed that participants showed significant improvements in time orientation and time management when using the watch. The young users rated the user experience as “excellent”, confirmed by newly acquired skills, expected learning effects, and enjoyment during use. Care personnel, as secondary users, reported a reduction in stress, which facilitated improved time management and enhanced the quality of care provided. In future work, we will strive to extend our research by long-term examinations to understand learning effects and quantitative effects on independence and autonomy.