Is it worth swimming in shark-infested waters to surf a 50-foot, career-record wave? Is it riskier to make an action movie or a horror movie? And should sex workers forfeit 50 percent of their income for added security? Bringing an unusual and often witty perspective to such questions, economist Allison Schrager points out that we all take risks every day, but few know how to maximize the chances of success. Providing five principles for dealing with risk, Schrager interviews a professional poker player, a paparazzo, horse breeders in Kentucky, and a general who led troops in Iraq, to better understand how to prepare for what we don't see coming.