Mindfulness [Langer (Mindfulness. Addison-Wesley, 1989)] has been shown to accrue innumerable health and psychological benefits to those who practice it [Langer and Moldoveanu (Journal of Social Issues 56(1):1–9, 2000)]. Given such remarkable outcomes, the question becomes—why not be mindful? In this chapter, Langer’s theories of mindfulness (1989) and control (1983) are linked to a motivational theory that illustrates how a focus on outcomes (even good outcomes) prevents persons from stably inhabiting a mindful state, and all its subsequent positive outcomes. The path to overcoming this paradoxical obstacle, and toward a process orientation [Langer (The psychology of control. SAGE, 1983)] that is necessary for mindfulness, is outlined.