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As medical learners progress through their training, compassion and empathy decrease, while cynicism increases. Though factors contributing to this evolution, such as fatigue and workload, have been identified, the process through which these changes occur has not been studied in detail. Our goal was to explore this process, mapping out key points in the transition which might be targetable for educators and leaders. Consequently, we conducted a qualitative study in the qualitative descriptive approach, analysing the process through which compassion and empathy decrease and cynicism increases over time. First, we collected Reddit narratives to develop an understanding of the process from a variety of perspectives. Subsequently, we invited participants (medical student to attending physician) to provide detailed descriptions of the process. 77 Reddit narratives and eight participant descriptions comprised 85 data slices. Analysis of the data identified four steps through which compassion and empathy are generally lost, and cynicism increased. Steps consisted of a real-world awakening to the realities of the medical field, interpersonal struggles compounded by lack of support, realised emotions in response to these realities and struggles, and development of a coping mechanism. While this process is not a unidirectional, linear one, these four steps help to describe how the evolution from compassionate, empathetic junior learner to more cynical physician occurs. This offers several concrete potential points of intervention and study for future work.