In 1964 John Caldwell Holt published his first work, How Children Fail. A teacher, and an observer of children and education, Holt asserted that the academic failure of schoolchildren was not in spite of the efforts of the schools, but actually because of the schools. Not surprisingly, How Children Fail ignited a firestorm of controversy. Holt was catapulted into American popular culture to the extent that he made appearances on major TV talk shows, wrote book reviews for Life magazine, and was a guest on the To Tell The Truth TV game show. In his follow-up work, How Children Learn, 1967, he tried to demonstrate the learning process of children and why he believed school short circuits this process. Such claims fail to account for the success of many schools, nor allow for the fact that diverse public and private schools in the US have a wide variety of teaching methods and philosophies.
In neither book had he suggested any alternative to institutional schooling; he had hoped to initiate a profound rethinking of education to make schools friendlier toward children. As the years passed he became convinced that the way schools were was what society wanted, and that a serious re-examination was not going to happen in his lifetime.
Leaving teaching to publicize his ideas about education full time, he encountered books by other authors questioning the premises and efficacy of compulsory schooling, like Deschooling Society by Ivan Illich, 1970, and No More Public School by Harold Bennet, 1972 (which went so far as to offer advice to parents on how to keep their children out of school illegally). Then, in 1976, he published Instead of Education; Ways to Help People Do Things Better. In its conclusion he called for a "Children's Underground Railroad" to help children escape compulsory schooling.
In response, Holt was contacted by families from around the U.S. to tell him that they were educating their children at home. In 1977, after corresponding with a number of these families, Holt began producing a magazine dedicated to home education: Growing Without Schooling.
A former WWII submariner, with no professional training in education, Holt's philosophy was simple: "... the human animal is a learning animal; we like to learn; we are good at it; we don't need to be shown how or made to do it. What kills the processes are the people interfering with it or trying to regulate it or control it." It was no great leap from there to arrive at homeschooling, and Holt later said, in 1980, "I want to make it clear that I don’t see homeschooling as some kind of answer to badness of schools. I think that the home is the proper base for the exploration of the world which we call learning or education. Home would be the best base no matter how good the schools were."
Holt actually wrote only one book about homeschooling, Teach Your Own, 1981, and continued to hope for more expansive reform within education until his death in 1985.