People's lived experiences of chronic illness have garnered increasing research interest over the last 30–40 years, with studies recognising the disruptive influence of illness onset and progression, both to people's everyday lives and to their biographical selves. We extend this body of work, drawing on the experiences of people living with Ménière's disease; a long-term progressive vestibular disorder characterised by unpredictable episodes of debilitating vertigo, tinnitus and permanent sensorineural hearing loss. In response to calls for more critical examination of the wider biographical contexts in which chronic illnesses are encountered, we draw on 28 in-depth narrative interviews with Ménière's patients and their family members to discuss how personal chronic illness experiences may be closely entwined with, and deeply shaped by, the life transitions (illness-related and otherwise) of ‘linked others’. Interviews were conducted in south west England from January to June 2015. Focusing on intersecting transitions of parenthood, caregiving and retirement, we explore how and why familial relationships can both facilitate and hinder adaptation to a lifetime of chronically disrupted normalities, contributing to fluctuating experiences of ‘cherished time’, ‘anomalous time’ and ‘turbulent time’. In so doing, we suggest that the onset and progression of chronic illness could usefully be re-conceptualised as one of many ‘biographical oscillations’ encountered during the life course that serve to re-route us between continually shifting life trajectories. In recognising life's dynamism and challenging the identity-limiting and self-damaging nature of entrenched cultural life course constructions, we suggest value in recognising alternative ways of ‘living well’ when negotiating the wide-ranging biographical maps that life can follow.