Career decisions are amongst the most important we make. Unsurprisingly, much published research exists on this particular aspect of career behaviour. However, the overwhelming majority of studies have been carried out on young people making initial career decisions. This paper extends our understanding by examining how mid-career adults in three European countries (Denmark, France and Italy) actually make career decisions. Characteristic patterns of behaviour recur when individuals approach points of transition or of crisis; each of these transitioning styles is illustrated by an iconic case. Emergent findings support the growing body of evidence that challenges the dominant policy and practice orthodoxy, which places rationality at the centre of the process, by recognising the importance of emotion and context.