Deciding against an academic career, Herb matriculated at Teachers College, Columbia in 1961, and in 1962 received an MA in teaching, while qualifying for a permanent kindergarten through eighth grade teaching certificate in the New York City public schools. In 1962 he became a sixth grade teacher in the New York City public schools, something he had dreamed of doing since childhood.

Herb has been teaching and writing for over forty-five years.  During that time he's taught every grade from kindergarten through graduate school, not in that order.  His career as a teacher began in 1962 in Harlem, where he continued to work for six years.  From September, 1964 to June, 1967, under a grant from the National Institute of Education, he ran a storefront school for junior high and high school students, taught high school psychology and writing, and worked as curriculum coordinator for the Parent Board of the I.S. 201 Community School District.  In 1966 he became the founding director of the Teachers and Writers Collaborative, a project intended to transform the teaching of writing in the schools.  He is still a Board member of the Collaborative.

In 1964 Herb's first book, ''The Age of Complexity'', about analytic and existential philosophy, was published at the same time that he was teaching sixth grade.  His first writings on education, ''Teaching the Unteachable'' (New York Review of Books, New York, 1967), and ''The Language and Education of the Deaf'' (The Urban Review Press, New York, 1967) set the themes for much of his future work.  They centered on advocating for the education of poor and disabled students, and critiquing and demystifying the stigmatization of students perfectly capable of learning.

In 1967, ''36 Children'' (New American Library, New York, 1967) was also published and Herb was drawn into national debates on the education of African American and other minority students, and into conversations on school reform and the nature of teaching and learning.  He's still engaged in them now, forty-two years later, having lived through cycles of reform and reaction, none of which succeeded in creating excellent education for the children of the poor.  The problems persist, and he still believes that, through hard, imaginative effort, they can be solved.

In 1968 Herb moved to Berkeley California where his family lived for the next nine years.  He was a Visiting Associate Professor, half time in the English Department and, the other half time, in the School of Education at the University of California, Berkeley during the spring semester of 1968.  At that point he received a grant from the Carnegie Corporation of New York (September 1968 to June 1969) to work with Allan Kaprow, the “happener,” who was a Professor of Art at the State University of New York, Stoneybrook, on teacher education and the development of creative curriculum that crossed disciplinary and artistic boundaries.  Working with Kaprow freed him to cross boundaries, work with students in theater, and experiment with interactive media.  This unlikely marriage, made by Margaret Mahoney of Carnegie, had a profound influence on Herb's teaching and thinking about learning.

An alternative high school, Other Ways emerged during that collaboration and it was supported, in 1969 by a grant from the Ford Foundation (September 1969 to June 1970).  This was one of the first attempts to create a series of alternative educational options within public school systems.

In 1972 Herb became co-director of the teacher education program at the Center for Open Learning and Teaching, and taught a combined kindergarten first grade at a Berkeley public elementary schools, while acting as a master teacher for their teacher education students.

For ten years (1970 to 1982) he wrote a monthly column for ''Teacher Magazine'', and contributed many reviews and articles for publications such as ''The New York Times, The London Times, The Nation, and The New York Review of Books''.  Herb also wrote a number of books during that period including ''The Open Classroom, Golden Boy as Anthony Cool, Reading, How to, A Book of Puzzlements, Mathematical Puzzlements, On Teaching, Growing With Your Children, and Half the House.''

In 1976, Herb and his wife Judith wrote ''The View from the Oak'', which won the 1977 National Book Award for Children's Literature.

In 1977 they moved to Point Arena, California and established the Coastal Ridge Research and Education Center.  Over the years the Center has sponsored a summer camp where he taught theater, and hosted a number of seminars on education and social justice.  These seminars have involved educators such as Myles Horton and Septum Clarke of the Highlander Center, Joseph and Helen Featherstone, William Ayers, Len Solo, Ira Glaser, Norm Fruchter, Asa Hilliard, Courtney Cazden, Phillip Lopate, Cynthia Brown, and Ron Jones.  The Center also worked with Amnesty International developing a curriculum on conscience and human rights, and with the ACLU developing a Bill of Rights curriculum.

Herb also spent a year (1985—86) teaching in a one room schoolhouse in Point Arena, and created, under a grant from the Agency for International Development and the University of Massachusetts, Amherst, (June 1986-January 1986) a month long residential session and a semester’s internship in the New York City schools, for the heads of teachers' colleges from Botswana sponsored by the University of Massachusetts, Amherst.

During the 1980s Herb also spent time working with a number of pioneers in the computer world.  He was on the Board of the Atari Education Foundation and consulted with Allan Kay’s Vivarium Project of Apple Computers.  His work with computers also involved being a games columnist for ''Recreational Computing Magazine and Publish!'', spending several years (1983—1985) as Director of Software Development for ''Scientific American'', co-authoring four books on computer programming and games for Reston Publishing Company, and editing a series of books on games and computers for them as well.  Also during that period, as a member of the Executive Board of PEN, American Center, he established the PEN American Center West.

Herb continued writing over these years and teaching occasionally as a Research Fellow at the University of San Francisco.  He was the Gordon Sanders Professor of Education at Hamline University in St. Paul during 1988-89, and then later on, spent more time in the Twin Cities area, as Benedict Professor of Educational Studies at Carleton College in 1995.  During all of this time, he was engaged with developing pedagogical content and structure that would take advantage of the strengths and experiences of poor and minority students.

Throughout the 1980s Herb and his wife Judith worked with Myles Horton on his autobiography, ''The Long Haul'' (Doubleday, New York, 1990).  It won the Robert F. Kennedy book award in 1991.

From September 1994 to June, 1997 Herb had the opportunity to work, through a grant from the Aaron Diamond Foundation, with the Fund for New York City Public Education September.  The goal of the project was to design structures for the development of small, theme based and community oriented, schools of choice within the city’s public school system.  The Fund morphed into New Visions Schools and is engaged in implementing that work.

In 1997 Herb was appointed a Senior Fellow at the Open Society Institute, the US foundation that is part of the Soros Foundation Network.  From September, 1997 to June, 1999 he worked towards planning a funding strategy in education for the Foundation, and in the process, managed to support a number of projects that promise effective school reform.

Herb has found himself both teaching and writing throughout his adult life.  He feels that writing is a private matter, education a public one.  They play off each other, nurturing and informing each other.  Both are a source of energy and give him a feeling of being of use to others.  Among the books he published from 1982 to 1999 are: ''Basic Skills'' (Little Brown, Boston, 1982), ''Growing Minds'' (Harper and Row, New York, 1986), ''Making Theater'' (Teachers and Writers Collaborative, New York, 1988), ''I Won't Learn from You'' (The New Press, New York, 1994), and ''Should We Burn Barbar?'' (The New Press, New York, 1995), and ''The Discipline of Hope'' (Simon and Schuster, New York, 1998).

In the spring of 2000, after his Fellowship at the Open Society Institute was completed, Herb accepted the challenge of building a small, autonomous teacher education program centered on equity and social justice at the University of San Francisco (USF).  The Center for Teaching Excellence and Social Justice opened with twenty-five students in the fall of 2000.  The first year was supported by a special innovative grant from the President of USF (January, 2000 to January, 2001).  The next three years were supported by a grant from the William and Flora Hewlett Foundation (September, 2001 to June, 2004).  Under the terms of the grant, the Center also worked on reform in the Oakland and San Francisco school districts.

During this time Herb published a book of essays, ''Stupidity and Tears'' (The New Press, New York, 2003) and ''She Would Not be Moved'' (The New Press, New York, 2005).

In 2005 he left the program at USF after five years and accepted a year’s appointment as Eugene Lang Visiting Professor for Issues of Social Change at Swarthmore College during the academic year of 2005-06.

Herb returned to his home in Point Arena, California in the summer of 2006.  Storms and water damage during the spring destroyed his study and many of his books and resources.  It took months to rebuild, and some of the work is still going on.  Nevertheless he continued to write, and his book ''Painting Chinese'' (Bloomsbury, New York, 2007) was finished in Point Arena and published in 2007.

He continues to work with educators across the country. In particular he's currently collaborating with Kevin Truitt, formerly principal of Mission High School and currently Associate Superintendent of the San Francisco Unified School District, on a book about the complex, demanding, and often heart breaking lives of urban high school principals.  The book proposes a way of supporting principals that is a cross between psychotherapy and dramaturgy, which they tried out for three years and decided to call edutherapy.

Herb is also collaborating with Tom Oppenheim and the Stella Adler Acting Studio, of which he is Director, on advocating support for the arts as necessary components of any decent public education.  In conjunction with this book, so far he has interviewed artists such as Phylicia Rashad, Rosie Perez, Bill T. Jones, and Whoopi Goldberg, and educators such as Maxine Greene, Frances Lucerna, and Steve Seidel.  Many other people have indicated willingness to participate in the project.

In addition, a collection of his works, ''The Herb Kohl Reader'' (The New Press, New York, 2009) was published recently. Herb is also currently teaching an essay writing class in Point Arena and working on a book of personal essays.

At the center of all of his work is the belief that a quality education for all children is a pedagogical imperative and a social justice issue.

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