This paper documents the design exploration of a future-speculative concept for the Mumbai Kaali Peeli taxi envisioned for the year 2040. The project employs an iterative process that departs from conventional user-interview-based research, instead using an observational photo documentary to understand current user behaviours and aspirations, which were then extrapolated into possible future needs. Global taxi services were benchmarked to identify emerging directions in mobility, and a custom methodology was developed to study trends and derive core values shaping future transportation. These insights informed the creation of multiple future scenarios, which were evaluated using the Futures Cone model to determine preferred futures, forming the contextual foundation for the 2040 Kaali Peeli concept. The vehicle was then designed through a standard automotive design process, including mood boards, theme boards, iterative ideation, and 3D modelling, before being visualised within the defined future scenario. The report aims to examine questions related to the evolving identity of the Kaali Peeli, its cultural significance in Mumbai, and the aspirations influencing future mobility, while encouraging reflection on how taxi services may transform in the coming decades.