Chapter 5 investigates “seamlessly” networked self-tracking tools as symbols of idealized professional mobility and looks to the Quantified Self (QS) as a forum that responds to and registers these business challenges and ambitions. Technologists tend to fetishize frictionless digital mobility. Conversations with digital professionals who participate in forums such as QS, however, indicate that the attractiveness of well-networked devices resonates less with the emerging realities of wearable technology or consumer “needs and wants” (a concern thematized in Chapter 3) than the ideals of lasting and sustainable tech sector careers that are otherwise punctuated by instability and breakdown. These are the additional entrepreneurial desires that motivate the making of self-tracking technology and become embedded in its design. QS also acts as a practical source of mutual aid that facilitates the desired connectivity and agility of working bodies. This chapter thus investigates QS as an interface that reconciles the technological fantasy and its repetitious recital with the difficulties tech executives face in their personal lives and professional work.