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From the financial crisis to recent environmental disasters, willful blindness is a widespread problem with systemic and cultural causes. In charting the phenomenon, this article begins by examining power. Leaders often inhabit a “bubble” of power and, when confronted by risky situations, think in abstract terms and demonstrate a level of self-certainty that is removed from reality. Money exacerbates power and leads to decisions that are concerned only with profit, which can lead to reckless outsourcing and lack of accountability. Employees would often rather be wrong than alone, and they fear retribution if they articulate problems to their leaders. Many employees, in fact, do not believe executives who claim that they want to hear the bad news along with the good. As this article reveals, groupthink can be a barrier to progress and the greatest single cause of willful blindness may be the most basic — to build a sense of self-worth, leaders are often surrounded by people and data that confirm their beliefs.