Chaos”, “organic”, “contested”, “messy” are terms evidently used to describe the nature of Indian cities, as 60-80 % are nearly “unplanned” and “self-constructed”. However, these expressions stand antithetical to modern urban spatial practices of planning and planned development which are embedded in regimes of formality and legality. Many of the larger cities have some form of a Master Plan to anticipate its urban development and civic infrastructure. Despite their Master Plans, they are largely seen as “unplanned”. What implications do plans have, then, on the inherent form and the self-evident nature of Indian cities? The paper looks at the case of the capital city Delhi, which is in the process of visioning its future for the next 20 years through its ongoing Master Planning process. By 2041, the population of the city is expected to reach the 30 million mark, struggling with growing housing shortage, disparate urban expansion, growing pollution levels, job-loss growth. Bahn (2013) describes this “chaos that is urban development” as a consequence of planning. It is with these casualties of development, that this paper concerns itself. In that case, the paper demonstrates the learnings from the use of the interactive toolkit, ‘Kaun hai Master? Kya hai Plan?’ ( ‘Who is the Master? What is the Plan?’) which was used as a template to discuss planning processes and encourage citizens to become a part of the conversation on future plans for the city. The toolkit was designed as a part of the Main Bhi Dilli (‘I am Delhi too’) campaign, a civic society campaign in Delhi formed to inclusively reimagine the Master Plan 2041, of which the author is also a part. Premised on the key takeaways from workshops along with ethnographic study in the form of oral stories, and key policy documents, the paper discusses five narratives around the state of housing, basic services, livelihoods, public infrastructure and public transport. These stories are particular but also emblematic as they depict both the urban condition as well as the social and economic dimensions of the citizens. By telling these, the paper attempts to address the gap between the final rhetoric of the Master Plan and the dynamic reality of people and its urban condition, using bottom-up planning approaches.