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Deschooling is a complicated term and arises in discussions of various alternative forms of education such as free schools, community-driven opportunity webs, and in the current literature related to the homeschooling movement. Deschooling was introduced in 1971's Deschooling Society, written by Ivan Illich and included in the World Perspectives book series edited by the humanist philosopher, Ruth Nanda Anshen. In suggesting the disestablishment of schools—thus nurturing the opportunity for each person to engage in a curriculum of learning, sharing, and caring—Illich's writing was representative of the work of Anshen's series as a statement of possibilities in a progressive frame of social and moral consciousness.

Illich credits his long-term associate, Everett Reimer, for stimulating his interest in and critique of public education. Reimer and Illich collaborated on ideas of deschooling a variety of societal institutions in addition to education—institutions such as medicine, social programs, the military, and so on—during regular meetings at the controversial Center for Intercultural Documentation (CIDOC, cofounded by Illich in 1961) in Cuernavaca, Mexico. The two men came to the conclusion that the obligatory nature of the institution of school served to limit a person's right to learn and, broadly, that reliance on institutions and institutional processes served to preempt expectations for and reliance on personal goodwill. Even further, Illich and Reimer believed that the growing institutionalization of society served to strengthen and perpetuate the institutions in society. Illich credited Valentine Borremans, the director of CIDOC, for challenging him, in collaboration with Reimer, to engage in a perspective that led them to determine that it was not only the institutions of society, but the ethos of society that ought to be deschooled.

Illich's discussion of deschooling included references to the terms tool and conviviality. He argued that the institution of school is used as a tool that, through its systematic methods and schedules, reinforces the class hierarchies and economic inequities that, ironically, the institution of school purports to rectify. Although good curriculum work requires complicated decisions and conversations, becoming “schooled up” by policies of standardized management uncomplicates school. Since most people are now all schooled up, the myth continues that the institution of schooling is efficient and benevolent.

For Illich, people were schooled to become more regimented, exploited, certified, and enslaved, losing their potential for creativity, potency, autonomy, freedom, novelty, and dignity. In contrast to a schooled-up society, Illich proposed a convivial society of curriculum scholarship that would allow autonomous and generative interactions among persons and their environments by means of tools least controlled by others. He considered conviviality as an individual freedom realized in personal interdependence and so, supportive of good curriculum work of relational and ethical value toward the common good.

Currently, deschooling is a term used by the homeschooling community to refer to the process of shifting away from the schooled mind-set after leaving the institution of school. It is also used in describing a period of time (many suggest 1 month for every year of institutionalized schooling) for children to adjust to learning without the regimentation of bells, workbooks, checklists, and standard schedules for learning.

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