The Saskatchewan Caregiver Experience Study sought to map the experiences of family and friend caregivers of older adults in the Canadian province of Saskatchewan. This study aimed to capture the lived experiences of these caregivers through a qualitative survey in June and July of 2022. This manuscript analyzes responses from 354 participants to the question: “What is the most challenging aspect of being a caregiver?” An inductive content analysis approach was taken to analyze the data. We identified key challenges related to caregiving in Saskatchewan, Canada, including exhaustion, balancing personal life, navigating complex systems, self-doubt, and caregiving from a distance. Participants emphasized the need for targeted support and interventions to assist them in their caregiving role. Participants’ experiences reflect a need for more supportive measures in healthcare and policy, especially considering the unique demographic and geographic context of Saskatchewan. A paradigm shift is needed toward supporting caregivers to allow older adults to age in place, rather than relying on institutions and care facilities. In the global context, these findings align with the need for culturally sensitive and region-specific support systems, addressing the universal aspects of caregiving.