Education quite often sends the message that life involves choosing a "thesis" and defending it against objections. Educators frequently require students to "pick a side," justifying their positions with the best reasons available. What should educators teach students about the value of holding opinions and beliefs? Should they believe in belief? Are there costs to living an "opinionated" life? In this paper, the author focuses on one particular version of ancient skepticism, the Pyrrhonian version. Other versions, such as the so-called Academic Skepticism of Carneades, had a more Socratic feel and lacked the emphasis on the alleged emotional benefits of skepticism. Based on what can be gleaned from other early Pyrrhonists, it seems that Pyrrho's version of ancient skepticism held that the mind has no access to things apart from sense perception, that sense perception does not guarantee that we perceive things as they really are, and therefore, that there is no way to know the true nature of things. The author posits that education should be, at least in part, about promoting human happiness. In this article, Warnick conceptualizes happiness largely in terms of "subjective wellbeing." This is a bit more expansive than the Pyrrhonian view of "ataraxia." Subjective wellbeing posits happiness as a combination of overall life satisfaction and a regular experience of positive emotions. Factors influencing subjective wellbeing include: family, friends, community, financial stability, health, freedom, rewarding work, and values. In this analysis, Warnick focuses on whether being opinionated contributes to these sorts of things.