Unpredictably fluctuating environments create complex selective landscapes that shape the distribution of key life history traits. Identifying the mechanisms behind dynamic patterns of selection is difficult, yet essential for predicting responses to climate change. We combine long-term measures with field manipulation of natural selection on breeding date in a wild bird to investigate whether highly variable spring cold snaps drive fluctuating selection. We show that variation in cold snap intensity leads to fluctuating selection on breeding date-in weak cold snap years, selection was consistently negative; however, in strong cold snap years, its direction reversed. These patterns were mirrored in a field experiment; nests that were food supplemented during cold snaps avoided cold snap mortality leading earlier breeders to have higher fitness. In contrast, in the non-supplemented group earlier breeders had higher cold snap nest mortality and selection was positive. Using nearly a century of climate data, we show that cold snaps are becoming less frequent and paradoxically occurring later which should allow earlier breeders to avoid them, potentially releasing conflicting selection pressures and facilitating a rapid phenological shift. Thus, rather than constraining a species' ability to adapt, climate change can enable a rapid shift to a new phenotypic optimum.