Wearable, intelligent, and unobtrusive sensor nodes that monitor the human body and the surrounding environment have the potential to create valuable data for preventive human-centric ubiquitous healthcare. To attain this vision of unobtrusiveness, the smart devices have to gather and analyze data over long periods of time without the need for battery recharging or replacement. This article presents a software-configurable kinetic energy harvesting and power management circuit that enables self-sustainable wearable devices. By exploiting the kinetic transducer as an energy source and an activity sensor simultaneously, the proposed circuit provides highly efficient context-aware control features. Its mixed-signal nano-power context awareness allows reaching energy neutrality even in energy-drought periods, thus significantly relaxing the energy storage requirements. Furthermore, the asynchronous sensing approach also doubles as a coarse-grained human activity recognition frontend. Experimental results, using commercial micro-kinetic generators, demonstrate the flexibility and potential of this approach: the circuit achieves a quiescent current of 57 nA and a maximum load current of 300 mA, delivered with a harvesting efficiency of 79%. Based on empirically collected motion data, the system achieves an energy surplus of over 232 mJ per day in a wrist-worn application while executing activity recognition at an accuracy of 89% and a latency of 60 s.