The Indian IT sector, being one of the major contributors to the country’s GDP is going through a transformational phase with the advent of new technologies like AI, Big Data and Blockchain. Despite this, a major problem rattling the industry is the lack of work-life balance among the employees due to overtime work. Yet they actively engage in overtime considering the mutual short-term gains which later impacts the long-term growth of the industry as a whole. 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 employee and the organization. The study employs a design led qualitative research approach by utilizing a series of creative tools such as story simulations, speculative 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. The study also presents a novel employee-centric empirical model to redefine how work-hours are measured, managed, and allocated. The findings of this study can be utilized in designing aspects like work load allocation, hybrid work scheduling, trade-off estimation between hiring and overtime, and policy level interventions both at organization level and government level.