Older adults and their family caregivers experience nursing home placement as a particularly critical time of life. The present study explored the experiences of family caregivers of nursing home residents taking part in a self-help group for caregivers. The sample was composed of six caregivers of older adults residing in a nursing home in the northeast of Italy. The respondents, aged 57 to 71, were part of a self-help group set up by the facility between 2017 and 2019. In this qualitative methodological design, we applied the principles of interpretative phenomenological analysis. Two main themes emerged from the interviews: (a) challenges in constructing experience as caregivers; and (b) shared experiences as stabilizing tools. The findings highlight the importance of self-help groups in fostering the well-being of caregivers of older adults living in nursing homes. The self-help group enabled caregivers to deal with nursing home placement and the sense of guilt deriving from it; understand and accept the disabilities affecting their loved one; comprehend the experience of ambiguous loss; and learn to listen to their own needs, thus avoiding physical and emotional exhaustion.