Humans live our lives in a dialectic of knowledge and ignorance. Knowing – or hoping – that knowledge is power and that ignorance is no bliss, most humans want to know. They wish to reduce their epistemic uncertainty and the insecurity that comes with that. States of uncertainty are most poignant when they depend on other people, and especially those who have their own strategic interests and who are able and willing to deploy the arts of deception. These limitations to knowing, stacked one on top of the other, can make the soundest mind feel insecure. The experience of insecurity, we submit, is affect-imbued social uncertainty. Lacking the conceptual tools to solve the problem of insecurity, we address four tractable challenges of uncertainty. In the first section, we consider strategic reasoning from a game-theoretic perspective. In the second section, we turn to the trust game, where uncertainty is amplified due to an interplay between strategies of coordination and discoordination. In the third section, we consider folk beliefs about free will and uncertainty, and show how they are related to one another, and how they are socially evaluated. In the last section, we explore how human freedom may grow from a strategic randomization of options and actions. Whether such strategies reduce or increase a person’s sense of insecurity likely depends on the person’s character. Freedom, we suspect, is not for everyone.