This paper presents a qualitative study of two focus group discussions on Singapore's state of current and future urban mobility. The findings of this study, which applied a grounded theory approach of analysis, led to the development of a theoretical framework that displays the dynamic interrelationships between individuals' external and internal influences, and their roles in shaping individuals' travel mode behaviors and future mobility expectations. This framework also shows the complex process by which individuals evoke value negotiations and adjustments before arriving at their desirable choice of travel mode. Coping mechanisms or strategies are also innovated by commuters when the available mobility services are not perceived to meet their value expectations and needs for different commuting purposes. The variables constituting the external and internal influences of our theoretical model remind us that a “typical” transport user should be ideally considered and defined in light of some fundamental parameters. The findings of this study are expected to benefit policymakers in identifying and navigating potential barriers and drivers of change that could support the formulation of future transport policies and the adoption of transport technologies.