Many of our experiences are unpredictable and radically changed by rare events. Although our conventional thinking is useful for maintaining the status quo, it is unable to anticipate or cope with unprecedented events . Just think of the unanticipated political consequences of the 9/11 terrorist attack, the iatrogenic effects (treatment induced negative side effects) of taking statins to reduce cholesterol (15% of the patients experience serious complications such as muscle weakness and cognitive dysfunction) or the 44 percent increase risk of dementia in people age 75 or older who regularly take heartburn medications called proton pump inhibitors (PPIs) such as Prilosec, Nexium and Prevacid, the elimination of book stores by Amazon’s success, or how computer failures can shut down air travel. One of the most thoughtful and brilliant authors who cuts through the cloud of conventional thinking and teaching is Nassim Nicholas Taleb. His books offer useful guidelines how to think about risk when interfacing with medicine or how to make healthy lifestyle choices. Begin by reading The Black Swan: The Impact of the Highly Improbable and then enjoy his recent book, Antifragile-Things that Gain from Disorder.