Reproduction in an uncertain world is fraught. The consequences of investing in too many offspring in a resource poor season can be disastrous but so too is missing the opportunity of a resource rich year. We consider a simple population and individual growth model and use Lyapunov exponents to find analytical results for the optimum brood size under stochastic environmental conditions. We show that if the environment shows dramatic changes between breeding seasons choosing a smaller brood size is more likely to be successful but the best strategy is to synchronize your reproduction to the food availability. Finally, we show that if the cost of having offspring is high it can be better to live in a highly varying world with a plastic strategy that synchronizes to the environment than to live in a deterministic world with a constant strategy, a finding with implications for invasive species and climate change.