This paper investigates the way different sides of grit inuence behavior. We showthat, in addition to grit's well-known upside in achieving economic success, it has apotential downside too. Specifically, we conduct an experiment using a game of luckand elicit each individual's intended plan of action and compare it to actual choice. Wefind that grittier individuals have a higher tendency to overplay. We then split grit intotwo new categories, tenacity and diligence, and obtain that tenacity alone captures thedifficulty in respecting ex-ante preferences when this means accepting defeat. Bothcomponents of grit correlate with lower self-reported procrastination problems andhigher self-esteem, with diligence being the more beneficial trait. Overall, the resultsindicate that diligence has a clear upside while tenacity has both the upside of notgiving up and the downside of not letting go.