In two experiments, we tested the hypothesis that strategy performance on a given trial is influenced by the difficulty of the strategy executed on the immediately preceding trial, an effect that we call strategy sequential difficulty effect. Participants' task was to provide approximate sums to two-digit addition problems by using cued rounding strategies. Results showed that performance was poorer after a difficult strategy than after an easy strategy. Our results have important theoretical and empirical implications for computational models of strategy choices and for furthering our understanding of strategic variations in arithmetic as well as in human cognition in general.