This paper is about guessing: how people respond to a question when they aren’t certain of the answer. Guesses show surprising and systematic patterns that the most obvious theories don’t explain. We argue that these patterns reveal that people aim to optimize a tradeoff between accuracy and informativity when forming their guess. After spelling out our theory, we use it to argue that guessing plays a central role in our cognitive lives. In particular, our account of guessing yields new theories of belief, assertion, and the conjunction fallacy—the psychological finding that people sometimes rank a conjunction as more probable than one of its conjuncts. More generally, we suggest that guessing helps explain how boundedly rational agents like us navigate a complex, uncertain world.