Scenario techniques have already produced useful insights into creating the visions about the future of mobility as well as the potential implementation challenges associated with these visions. Unfortunately, scenario outcomes may appear to be an oversimplification of what is known as a complex issue in transportation, especially in determining how the future might unfold. The ‘traditional way’ of developing qualitative scenarios such as visioning activities often foreshadow the existence of a single best or a limited future option(s) for a given sector, community, or area. This is problematic as it views the target population as homogeneous, even though recipients may diverge widely in their value judgments over what a desirable future might be. As a result, without explicitly eliciting and negotiating this contested territory, scenario development runs the risk of creating opposition to sustainability futures rather than creating a common ground for different worldviews. In an effort to directly address the oversimplification that may be an artefact of the scenario planning process, we extend the scenarios developed in the scenario planning workshop on the Future of Urban Mobility conducted in Singapore to discover other ‘missing’ storylines that might be plausible but were not identified by the workshop participants. A scenario discovery method called the cross-impact balance (CIB) analysis will be employed to search for plausible alternative scenarios especially scenarios that were not discovered by the participants of the scenario planning workshop. Ultimately, we craft strategies that could be employed to trigger imaginative, transformative vision of the future, while navigating complex and potentially contradicting worldviews.