Having a poor start in the labour market has a ‘scarring’ effect on future employment and well-being. Indeed, unemployment at any point of the life-course can scar. While there is extensive quantitative research examining scarring effects at the macro- and meso-levels, evidence regarding scarring from the micro-level that provides insights into individual perceptions, values, attitudes and capabilities, and how they shape employment trajectories is lacking. A qualitative approach which avoids the imposition of values and choices onto individuals’ employment trajectories, and accounts more fully for the contextual constraints which shape available options and choices, is argued for. In emphasising people’s substantive freedom of choice, which may be enabled or constrained by contextual conditions, the Capability Approach is proposed as providing a valuable lens to examine complex and insecure labour market transitions. Such an approach stands in contrast to the supply-side focused active labour market policies characteristic of neo-liberal welfare states.