Empirical studies of life histories often ignore stochastic variation, despite theoretical demonstrations of its potential impact on life-history evolution. Here we use a novel approach to explore the effects of stochastic variation on life-history evolution and estimate the selection pressures operating on the monocarpic perennial Carlina vulgaris, in which flowering may be delayed by up to eight years. The approach is novel in that we use modern theoretical techniques to estimate selection pressures and the fitness landscape from a fully parameterised individual-based model. These approaches take into account temporal variation in demographic rates and density dependence. Analysis of 16 years' data revealed significant temporal variation in growth, mortality, and recruitment in our study population. Flowering was strongly size dependent and, unusually for such a species, also age dependent. Individual-based models of the flowering strategy, parameterized using field data, consistently underestimated the size at flowering, when temporal variation in demographic rates was ignored. In contrast, models that incorporated temporal variation in growth, mortality, and recruitment predicted sizes at flowering not significantly different from those observed in the field. Temporal variation in mortality, which had the largest effect on the flowering strategy, selected for increased size at flowering. An analytical approximation is presented to explain this result, extending the “1-year look-ahead criterion” presented in Rees et al. (2000). A fitness landscape generated by following the fate of rare mutant invaders with a broad range of alternative flowering strategies demonstrated that the observed parameters were adaptive. However, the fitness landscape reveals that approximately equal fitness is achieved by a broad range of strategies, providing a mechanism for the maintenance of genetic variation. To understand how the different parameters that defined our models determine the fitness of rare mutants, we numerically estimated the elasticities and sensitivities of mutant fitness. This demonstrated strong selection on a number of the parameters. Elasticities and sensitivities estimated in constant and random environments were significantly positively correlated, and both were negatively related to the standard error of the parameter. This last result is surprising and, we argue, reflects the genetic and phenotypic responses to selection.