Many generalist species are composed of individuals varying in the size of their realized niches within a population. To understand the underlying causes and implications of this phenomenon, repeated samplings on the same individuals subjected to different environmental conditions are needed. Here, we studied individual specialization of feeding strategies in breeding and non-breeding grounds of Cory’s shearwaters (Calonectris borealis) for 2–8 years, and its relationship with fitness. Individuals were relatively flexible in non-breeding destinations, but specialized in diet, habitat use and daily activity across years. Daily activity was also consistent throughout the year for the same individual, suggesting that it is driven by individual constraints, whereas individual diet and habitat use changed between breeding and non-breeding grounds, indicating that these specializations may be learned at each area. Moreover, individuals that were intermediate specialized in their diet tended to show higher breeding success than those with weakly and highly specialized diets, suggesting stabilizing selection. Overall, this study suggests that the development of individual specialization is more flexible than previously thought, i.e. it emerges under specific environmental conditions and can develop differently when environmental conditions vary. However, once established, individual specialization may compromise the ability of individuals to cope with environmental stochasticity.