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Imitation of excellence is only removed by a few degrees from idolizing perfection: the sin of perfectionism. Classical Christian students (and parents and educators) are particularly prone to placing superhuman expectations on themselves in areas from grades to godliness. When we perfectionists inevitably fail, we disguise our flaws, work harder, hide behind masks, shut people out, and pretend to have it all together while fear, shame, and isolation continue to grow. In academic contexts where high standards, hard work, and discipline are celebrated, the idolatry of perfectionism looks dangerously similar to the imitation of excellence. Classical education often unwittingly fosters perfectionists and holds them up as examples when instead we need teachers, parents, and students who are able to fail, to be vulnerable, to ask for help, and to receive the grace of the Gospel.