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Uncertainty permeates decisions from the trivial to the profound. Integrating brain and behavioral evidence, we discuss how probabilistic (varied outcomes) and temporal (delayed outcomes) uncertainty differ across age and individuals; how critical tests adjudicate between theories of uncertainty (prospect theory and fuzzy-trace theory); and how these mechanisms might be represented in the brain. The same categorical gist representations of gains and losses account for choices and eye-tracking data in both value-allocation (add money to gambles) and risky-choice tasks, disconfrming prospect theory and confrming predictions of fuzzy-trace theory. The analysis is extended to delay discounting and disambiguated choices, explaining hidden zero effects that similarly turn on categorical distinctions between some gain and no gain, certain gain and uncertain gain, gain and loss, and now and later. Bold activation implicates dorsolateral prefrontal and posterior parietal cortices in gist strategies that are not just one tool in a grab-bag of cognitive options but rather are general strategies that systematically predict behaviors across many different tasks involving probabilistic and temporal uncertainty. High valuation (e.g., ventral striatum; ventromedial prefrontal cortex) and low executive control (e.g., lateral prefrontal cortex) contribute to risky and impatient choices, especially in youth. However, valuation in ventral striatum supports reward-maximizing and gist strategies in adulthood. Indeed, processing becomes less “rational” in the sense of maximizing gains and more noncompensatory (eye movements indicate fewer tradeoffs) as development progresses from adolescence to adulthood, as predicted. Implications for theoretically predicted “public-health paradoxes” are discussed, including gist versus verbatim thinking in drug experimentation and addiction.