The chapter reflects a personal and professional journey as a clinical psychologist supporting children, adolescents and families living with diabetes. It describes the burden of diabetes and its impact on developmental stages including childhood, adolescence, emerging adults, parents and grandparents from a systemic perspective, discussing how internalised and institutional stigma and burnout impact on self-care and treatment concordance. Halfway through writing the chapter my grandson was diagnosed with Type One Diabetes shifting my perspective from ‘knowing’ to ‘lived experience’. It also meant I couldn’t write the chapter on my own and invited Xander to help me. As a family, we try to do what I have talked to parents about for years—watching and supporting at a distance without taking over. I believed I understood and empathised with parents and young people over how difficult it was to ‘do diabetes’. I am now experiencing for myself how difficult this truly is. However much you ‘know’ how much of a challenge it is, you only feel it when you and the people you love are living it. Xander has helped me understand, more than ever that effective management must extend beyond medical treatment encompassing emotional well-being, social support and managing societal prejudices with patient-centred, strength-based approaches helping to recognise the intertwined personal, familial and systemic factors that influence positive outcomes. I have also learned that we professionals don’t always get it as right as we think we are do!