One of the most exciting yet stressful times in a physician's life is transitioning from supervised training into independent practice. The majority of literature devoted to this topic has focused upon a perceived gap between clinical and non-clinical skills and interventions taken to address it. Building upon recent streams of scholarship in identity formation and adaptation to new contexts, this work uses a Heideggerian perspective to frame an autoethnographical exploration of the author's transition into independent paediatric practice. An archive of reflective journal entries and personal communications was assembled from the author's first 3 years of practice in four different contexts and analyzed using Heidegger's linked existentials of understanding, attunement and discourse. Insights from his journey suggest this period is a time of anxiety and vulnerability when one questions one's competence and very identity as a medical professional. At the same time, it illustrates the inseparable link between practitioners and the network of relationships in which they are bound, how these relationships contextually vary and how recognizing and tuning to these differences may allow for a more seamless transition. While this work is the experience of one person, its insights support the ideas that change is a constant in professional practice and competence is contextual. As a result, developing educational content that inculcates contextual flexibility and an increased comfort level with uncertainty may prepare our trainees not just to navigate the unavoidable novelty of transition, but lay the groundwork for professional identities attuned to engage more broadly with change itself.