When investigating the feelings of caregivers to patients with T1DM, parental stress, anxiety, and depression are found to be most prevalent, especially in the diagnostic phase and in the first months after diagnosis. In this pilot study, we research various significant elements regarding the well-being of mothers with children between 10 and 15 years of age with a chronic condition. The study focuses on a period of at least three years after the child’s diagnosis. The aims of the study are to describe our sample’s levels of satisfaction (SWLS) and subjective happiness (SHS) and to evaluate possible associations. A sample of 40 mothers was offered a series of assessment tools about psychological skills that could play a role in improving mothers’ well-being: the use of specific coping mechanisms (CISS), the methods of narrating the experience of life with a son/daughter with diabetes, the sense of coherence (SOCS 29), health parameters vs. child’s disease (HbA1c, CBCL), and socio-demographic, such as education and work. The most significant associations with respect to subjective happiness are with the sense of coherence, as a unitary value and as distinct factors, and with task-oriented coping. Sense of coherence is also associated with satisfaction.