This paper explores the transitions between “my-time” and “your-time,” between different social roles, and between different technological contexts. We used shadowing, voice-mail diaries and semi-structured group interviews to investigate the limits of seamless mobility. We identified an interesting behavior we call a “peek”: a quick look ahead in order to prepare for transitions. We also found that people are able to able to infer a lot from very little contextual information, and we argue that technologies designed for the above transitions therefore should rely on a few, well-chosen pieces of presence/awareness data, rather than exhaustive information. As a guide to invention and design, this study underlines the need to recognize our users’ intelligence. Instead of making applications that anticipate what users wants to do, we suggest providing information that is relevant and clear enough that users can take a glance at it and decide for themselves how to proceed.