The ‘always on’ state of contextual interlacing, or blurring of contextual boundaries, through digital media has been said to indicate a structural and cultural shift in the balance between two key spheres of life: personal and work life (e.g., Gregg, 2011). This shift involves the perceived significance and importance of work over personal life as a source of meaning for people’s everyday lives and has further become a popular reference point for societal debates over work-life balance and stress (Berkowsky, 2013; Middleton, 2007). We posit that the premise for this cultural shift is developments at the level of communication. If we are indeed witnessing such underlying structural and cultural changes of the day-to-day life worlds we inhabit, these changes manifest themselves in individuals’ changing communication practices and management. In this paper, we analyze how Danes from all walks of working life orient themselves to, experience and manage the relationship between work and personal life by way of communicative practices and personal media configuration, including their regulation of availability through digital media. The analysis is based on empirical studies of two contemporary cases for the blurring of personal and work life, namely a) the use of enterprise social media and b) corporate wellness programs that assist employees in self-tracking, e.g., their health or their computer habits, and seek to help employees develop better habits that make them heathier, more productive, or achieve so-called work/life balance. Both cases are part of the modern connected workplace, address the ‘inner life’ and social kit of the organization and digital mobilizes media that many people already use in personal contexts and for personal communicative purposes: Social media and smartphone self-tracking devices and apps. With that, personal genres of communication are imported and adjusted in a professional context. Yet the cases represent different types of personal communication: Enterprise social media primarily affords many-to-many communication (Jensen, 2015; Lomborg, 2014), while self-tracking is first and foremost a case of auto-communication from a user to him- or herself (Lomborg & Frandsen, 2016), derived from the basic affordances of social media and self-tracking, respectively. We base the analysis of the two cases on observations, meeting minutes and interviews from six-months fieldwork with 20 employees at the main office of an international company based in Copenhagen, as well as media diaries and interviews with a purposive sample of (n = 40) Danes recruited to represent a mix of employment and career types, gender, and family situation, about their experiences of and strategies for managing the boundary between work and personal life. One key theme emerging across the empirical data is the perceived value of disconnecting to safeguard the intimate sphere and pursue analogue activities that supposedly are the hallmarks of the good life. Another is, paradoxically, the value of digital media themselves in providing data-based insights to foster the habits that enable personal wellbeing in pursuit of the good life.