The word ‘trauma’, used in everyday language, means a highly stressful event that provokes an interruption of ordinary life and time, such as when one receives a diagnosis of a serious or life limiting illness, or when one is incarcerated. A traumatic event or situation creates psychological trauma when it overwhelms the individual’s ability to cope, and leaves that person fearing death, annihilation, mutilation, or psychosis. The individual may feel emotionally, cognitively, and physically overwhelmed. Trauma comes in many forms, and there are vast differences among people who experience trauma. Using some tools coming from phenomenology, we can say that trauma disturbs the ek-static unity of temporality: it is an ‘event’ that irrupts in the life of a human being, devastating his or her existence. When this kind of ‘event’ enters into a life, everything changes. This chapter focuses initially on a personal journey of trauma, then follows the experience through an empirical research lens of this type of trauma as experienced by the incarcerated. Our analysis will proceed using a phenomenological approach, showing the peculiarity of a phenomenological psychopathology and hermeneutic phenomenology. We focus on trauma as a catalyst for healing. By examining the philosophical aspects of trauma, we can understand the foundations of the traumatic experience. From there we will move forward to show how the theoretical morphs into the psychological by analysing how trauma affects personality. Sociological applications will be addressed, particularly how trauma often leads to incarceration. Finally, the exploration will transverse the journey that several individuals have taken through their diagnoses of life-altering diseases, abuse and neglect that ultimately led to the loss of freedom and the trauma surrounding being incarcerated. Through their eyes, we will follow the journey that trauma takes to healing.