The aging of the Taiwanese population has become a major issue. Previous research has focused on the burden and stress faced by caregivers, but has not explored how the experience of these caregivers influences decisions of advance care planning (ACP). Semi-structured and in-depth interviews were conducted. Qualitative content analysis was used to identify important themes. Five themes and fourteen sub-themes were identified: (1) Past experiences: patient wishes, professional recommendations, and expectation about disease progress; (2) Impact of care on family members: positive affirmation, open-minded life, social isolation and health effects, and financial and life planning effects; (3) Attitude toward life: not forcing to stay, and not becoming a burden, (4) Expected proxy dilemmas: torment between doing or not, seeing the extension of suffering and toil, and remorse and self-blame; (5) Expectation of end of life (EOL) care: caregiver’s experience and EOL care decisions, and practicality of EOL decision making. After making multiple medical decisions for their disabled relatives, caregivers are able to calmly face their own medical decisions, and “not becoming a burden” is their primary consideration. It’s suggested that implementation of shared decision-making on medical care for patients with chronic disability will not only improve the quality of their medical care but also reduce the development of remorse and guilty feelings of caregivers after making medical decisions.