Kierkegaard is a philosopher who gave rise to a new understanding of philosophy and propounded that philosophy was not to be circumscribed within abstract concepts but needed to open an accessible touch with the practical facets of life. He suggested that philosophy’s task would transpire in a thoughtful examination of real lived experiences. Instead of an indulgence in the previously common philosophical practice of abstract-oriented concepts and categories, Kierkegaard embarked on bringing philosophy to the phenomenological realities of everyone’s life and highlighted how everyone can be in dire need of philosophical reflections. Langer is known as the psychologist who has profusely depicted the grace of mindfulness and its implications in interpersonal and intrapersonal life for the past 35 years. Her findings in the field of psychology have shown how our lives can be devoid of any presence when we experience mindlessness. Langer, through dozens of psychological experiments, has elaborated how mindlessness imposes paralysis of action and gets one stuck in his/her position of assumptions. She indicates how a self without mindfulness would lose his/her potential as he/she would drift from the process of becoming. This chapter examines the interconnection between Kierkegaard’s paradox and Langer’s psychology of possibility.