We are observing a monumental effort from the industry and academia to make everything connected. Naturally, to understand the needs of these connected things, we need a better understanding of humans and where, when, and how they interact. Then we can create digital services and capabilities that fundamentally change the way we experience our lives. Right now IoT is all about connectivity, and scale. Next generation IoT will be about learning and contextual automation. Designing intention- and behavior-aware services will be the principal source of differentiation, and competitive advantage for the industry players. To this end, in this talk I explore how wearable devices and Wi-Fi network can be used as a sensing platform to understand you and the world around you and to design future consumer facing connected services.