Well-being is a complex phenomenon that is deeply depends on the individuals themselves and includes subjective perception of the past, present and future experiences. Connecting with work adds a concrete dimension to that wellbeing that makes it possible to consider designing for well-being and assessing it. One key element related to well-being is engagement at work and gameful design is a mean to increase engagement. This position paper builds on the evolution of the field of HCI over the years to identify means of addressing wellbeing through engagement. We describe the concepts related to Usability and how they evolved towards User Experience to encompass more complex (related to self) elements. We show how previous work in the field has connected these two major properties (using tasks descriptions) and how it might be possible to extend further embracing human needs and motivation theory. A concrete example is given in the context of interaction with a digital clock. Even though this example is simple, it conveys the concerns and highlights possible directions towards solutions.