Individuals frequently confront various kinds of losses during their lifetime such as death of loved ones, financial losses, damage to health, among others. These challenges can have short-term or long-term impacts. Hence, adapting successfully to the impact of these challenges is an inevitable and sometimes an ongoing process in life. While some individuals display maladaptive behavior when faced with such adversities, others display resilience in adapting to them and eventually establish a state of well-being. This chapter presents four case studies of resilient individuals who have faced different challenges such as physical health, relationship loss, domestic violence, and child sexual abuse. There were two male and two female participants with a mean age of 32. The objective of the study was to explore resilience and well-being outcomes among individuals who have experienced adversity. A case study approach was considered suitable as it allows participants to report their subjective experiences, an opportunity that quantitative methods do not allow. Interviews were conducted using (McAdams, 1985) life story approach which covers factors ranging from childhood experiences to personality traits and peak experiences. The findings revealed that all participants eventually established a state of optimal functioning through resilience derived from internal and external protective factors. Major themes identified were negative experiences and emotions, positive emotions, benefit finding, presence of significant others, and pro-social behavior. Well-being was exhibited through positive consequences such as empathy, self-belief, and gratitude after facing hardship. The authors recommend using the case study approach in exploring resilience as individuals have unique coping mechanisms that are difficult to capture through quantitative measures. Additionally, case study approaches may be useful in understanding well-being outcomes in a variety of contexts which are otherwise difficult through preset questions. Finally, implications of the study and suggestions for future research have been proposed. © The Editor(s) (if applicable) and The Author(s), under exclusive license to Taylor and Francis Pte Ltd. 2022.