Diagnostic categorisation is a typical stage of the medical model. Nevertheless, it is important to consider what is helpful to both the clinician and the patient when symptoms, experiences and perceptions are categorised. In this case report, we address the problem of comorbidity and complexity in psychiatry. Research and clinical experience point to significant overlap between personality disorders, mood disorders, and developmental disorders such as attention-deficit hyperactivity disorder. In the face of such complexity, we discuss ways of addressing and managing multiple diagnoses in clinical practice. We synthesise the perspectives and views of a general practice trainee, two consultant psychiatrists and a person with lived experience.