At the urging of his sister, Holt became a fifth grade teacher. After several years of teaching in Colorado, he moved to Boston. It was here that he met Bill Hull, a fellow teacher, and they decided to start a classroom observation project; one would teach, while the other would watch. The notes and journal entries Holt accumulated during his first eleven years of teaching formed the core of two of his most popular books How Children Fail and How Children Learn, as well as his less-known and more radical work, Escape from Childhood: The Rights and Needs of Children. These three books detailed the foundational ideas of Holt's philosophy of education. He held that the primary reason children did not learn in schools was fear: fear of getting the wrong answers, fear of being mocked by the teacher and classmates, fear of not being good enough. This was worsened, he maintained, by children being forced to study things that they were not necessarily interested in.
It was 1964 when Holt published his first book, How Children Fail. In this book, 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 the American national consciousness 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 (published in 1967) he tried to demonstrate the learning process of children and why he believed school short circuits this process.
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 newsletter dedicated to home education, Growing Without Schooling.
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 continued to hope for more expansive reform within education until his death in 1985.
Holt's Growing Without Schooling (GWS), founded in 1977, was the nation's first home education newsletter. He also set up John Holt's Bookstore, which made selected books available by mail-order; this brought in additional revenue that helped sustain the newsletter, which carried only minimal advertising.
In 1981, Holt's sole book on homeschooling, Teach Your Own, was published, and quickly became the "Bible" of the early homeschooling movement.
In addition to favoring home schooling, Holt also espoused many of the principles now taken up by the Youth rights movement, including eliminating the voting age and allowing young people to sign contracts and obtain employment.
Education... now seems to me perhaps the most authoritarian and dangerous of all the social inventions of mankind. It is the deepest foundation of the modern slave state, in which most people feel themselves to be nothing but producers, consumers, spectators, and 'fans,' driven more and more, in all parts of their lives, by greed, envy, and fear. My concern is not to improve 'education' but to do away with it, to end the ugly and antihuman business of people-shaping and to allow and help people to shape themselves.
The most important thing any teacher has to learn, not to be learned in any school of education I ever heard of, can be expressed in seven words: Learning is not the product of teaching. Learning is the product of the activity of learners.
It's not that I feel that school is a good idea gone wrong, but a wrong idea from the word go. It's a nutty notion that we can have a place where nothing but learning happens, cut off from the rest of life.
No one is more truly helpless, more completely a victim, than he who can neither choose nor change nor escape his protectors.