This chapter explores automated decision-support for smart work through the case of Microsoft MyAnalytics, an AI-enhanced system for tracking and analysing employees’ digital work habits and nudging them to work smarter and more productively. In doing so, it engages with automation from the perspective of everyday AI that calls attention to forms of automated decision-making that go unnoticed, integrate seamlessly in daily life and are often seen to help users take charge of their daily duties. I address MyAnalytics as a case of pushed or even imposed self-tracking that communicates about the user and with the user about what is assumed to be healthy work habits for a good working life. I then draw on examples from empirical research about self-tracking at work to understand the role that MyAnalytics might play in the empirical realities of employees. I discuss various forms of engagement with MyAnalytics, from outright ignoring it to engaging selectively and purposefully with it, to show that a good and meaningful work life might look different from that communicated by the system, depending on the personal circumstances of the employee and the context of work in question. The analysis thus speaks to current debates around digital paternalism, nudging, and concerns over AI and restraint of human agency.