Self-driving vehicles have been heralded as a dramatic new advancement in personal mobility. This emerging technology, beyond potentially improving driving safety, also represents a redefined relationship between the human driver and the vehicle. As this artificial intelligence-based vehicular technology becomes more intelligent, conventional interaction design methodologies may be challenged in their ability to fully encompass this redefined relationship. This problem may be even more pronounced for specific populations like older adults (60+) whose perspectives, we argue, have been underexplored in the self-driving vehicle context. Within this report we describe an emerging methodology, user enactment, and explore its use as a generative design process in two studies focused on older adults. This work adds additional support to the contention that user enactment may be an effective methodological tool for researchers in exploring the relationship between humans and intelligent technologies.