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In this paper we examine the noteworthy development that D.W. Winnicott referred to as a “flight to sanity” and consider the ways in which this idea intersects with problems in education. A flight to sanity takes on the appearance of interacting with objective reality but in actuality, it involves interaction with an internal simulation of reality and involves the denial of one’s subjectivity. We argue that the current milieu in schooling policies and practices promotes such a flight to sanity. That is, we find that schools are increasingly sacrificing any semblance of creative living and the unexpected for the sake of the more sane than sane, often through ostensibly “healthy” packages like “College and Career Readiness.”