Humans regularly invest time towards activities characterized by dramatic success or failure outcomes, where criti-cally, the outcome is uncertain ex-ante. How should people allocate time between such make-or-break activities and other safealternatives, where rewards are more predictable (e.g., linear) functions of time? We present a formal framework for studyingtime allocation between these two types of activities, and explore (optimal) behavior in both one-shot and dynamic versions ofthe problem. In the one-shot version, we illustrate the striking discontinuous relation between peoples skill and optimal timeallocation to the make-or-break task. In the dynamic version, we formulate both fully rational and boundedly rational strategies,both defined by a giving up threshold, which adaptively dictates when one should cease pursuit of the make- or-break goal.Comparing strategies across environments, we investigate the cost of sidestepping the computational burden of full rationality.