Life-history theory predicts that current behaviour affects future reproduction, implying that animals should optimise their escape strategies to reflect fitness costs and benefits of premature escape. Both costs and benefits of escape may change temporally with important consequences for the evolution of escape strategies. Moreover, escape strategies of species may differ according to their positions on slow–fast pace of life gradients. We studied risk-taking in long-distance migratory animals, waders (Charadriiformes), during the annual cycle, i.e., breeding in Europe, stopover in the Middle East and wintering in tropical Africa. Phylogenetically informed comparative analyses revealed that risk-taking (measured as flight initiation distance, FID) changed significantly over the year, being lowest during breeding and peaking at stopover sites. Similarly, relationships between risk-taking and life-history traits changed among stages of the annual cycle. While risk-taking significantly decreased with increasing body mass during breeding, risk-taking–body mass relationship became marginally significant in winter and disappeared during migration. The positive trend of risk-taking along slow–fast pace of life gradient measured as adult survival was only found during breeding. The season-dependent relationships between risk-taking and life history traits suggest that migrating animals respond to fluctuating environments by adopting behavioural plasticity.