In today’s digital landscape, “day-in-the-life” content has grown significantly in popularity, with individuals sharing detailed insights into their daily routines across social media platforms. Whilst often perceived as harmless, this content can reveal far more than intended. This talk adopts an adversary's perspective to demonstrate how short, informal videos can be analysed to build detailed intelligence on both the individuals and the businesses they represent. Drawing on real-world case studies, the session will show how seemingly minor visual and contextual details can expose information about home environments, workplaces, routines, security practices, and operational processes. It highlights how low-risk content can quickly become a valuable intelligence source and outlines how organisations can better understand and mitigate this evolving exposure.