This paper examines how young people’s early transitions into the labour market have changed between cohorts born in 1958, 1970, 1980, and 1990. We use sequence analysis to characterise transition patterns and identify three distinct pathways in all cohorts. An ‘Entering the Labour Market’ group has declined significantly in size (from 91% in the earliest cohort, to 37% in the most recent), an ‘Accumulating Human Capital’ group has grown in its place (from 4% to 51%), but also a ‘Potentially Difficult Transition’ group has grown alongside this, reaching 12% in the most recent cohort. These trends appear to reflect behavioural rather than compositional changes. Females and those who are from a non-white ethnic background have gone from being more likely to be in the ‘Potentially Difficult Transition’ group, to being less likely. Coming from a low socio-economic status background has remained a strong predictor of having a transition of this type across all four cohorts. These early transitions are important, not least since we show they are highly predictive of longer-term outcomes.