The objective of this study is to holistically develop an understanding on why employees actively engage in overtime and the impact it has on both the em ployee and the organization. The study employs a design led qualitative research approach by utilizing a series of creative tools such as story simulations, specu lative activity simulation, productivity mapping, scenario recollection, love-hate letter and bingo, which are spread across 5 phases. By developing a systemic understanding of overtime culture in the Indian IT context, the study captures how overtime is a double-edged sword and is driven by both the employees and the organization due to lack of a nuanced understanding.