Older adults often find it difficult to keep track of their cognitive and functional abilities required for remaining independent in their homes. Healthcare providers need objective, timely, and ecologically valid information about their patient’s behaviors at home for assessing their patient’s condition and whether behavioral problems such as non-adherence are significant problems. Ubiquitous sensors in the home can be used to monitor patient-centered observations of daily living (ODLs) about how well individuals carry out specific tasks that indicate the individual’s abilities for living independently. This article demonstrates through a series of case studies that reviewing ODL data about medication taking, phone use, and coffee making can help individual improve their self-awareness of their abilities and also motivate them to improve their performance of their behaviors at least temporarily. This article also demonstrates how physicians when reviewing ODL data about their patient’s medication adherence, phone use, and coffee making provided new, provides relevant information for physicians to refine their care plans for their patients. The ODL data indicate to physicians which functional areas the patient was performing well and which areas the patient required closer follow-up or immediate attention. Integrating ODLs into clinical workflows remains a challenge; however, the case studies in this article highlight that the preferred setting to review ODL data was during the patient’s visit to the physician’s office, so the physician and patient can have a shared understanding of the patient’s functioning at home. More proactive reviews of ODLs can be triggered by well-tuned alerts received by other members of the clinical team or informal care network. In summary, observations of daily living about the everyday actions of individuals, if reviewed, can result in greater awareness, motivation for improving behaviors, and better-informed decision making about an individual’s health care, enabling individuals to maintain their functional abilities as they age.