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Why is it so hard to find a progressive school these days?
The Education We Know Is Possible
There is something both encouraging and slightly melancholy about sitting down with Alfie Kohn to discuss progressive education. Encouraging because his thinking remains as sharp and generative as ever, and because the people who gather around conversations like ours — the Independent School Leaders Forum — still burn with the same conviction that drove Dewey, drove Maria Montessori, drove my mother when she was up at Columbia in the nineteen-twenties absorbing ideas that seemed radical then and remain, somehow, radical still. Melancholy because so much of what we talked about has been talked about for a hundred years. The question Alfie turned back on us is the one we can never quite escape: if we know all of this, if we can articulate it so clearly and feel it so deeply, why are there still so few schools that actually live it?
That is where I want to begin, and I want to be honest with you about the answer, because I think school leaders sometimes look for an easier explanation than the truth provides.
What We Mean by Progressive
Alfie opened by doing something characteristically useful. He refused to let the word progressive do unchallenged work. Is a school not progressive because it charges $50,000 a year? Does a genuinely progressive lower school become something else when the students reach middle school and the culture shifts toward preparation and performance? What about the school that teaches interdisciplinary humanities with real depth and collaboration, but still hands out worksheets in math? And what about — this is the one that stings the most — the school that talks beautifully about progressivism in its political and cultural dimensions, that is genuinely concerned with justice and the environment and the full humanity of every child, but that still runs on a hidden grammar of obedience, graded performance, and adult control?
This last type is more common than we like to admit in our community. Alfie put it plainly: some schools are progressive in the contemporary political sense of that word but are not doing progressive education as any of us — Dewey, Montessori, Piaget — would define it. They teach about American imperialism and saving the planet, and they still give quizzes. The content has changed; the relationship between teacher, child, and knowledge has not.
What matters, Alfie insisted, is not the label but the substance. And the substance, drawing on the tradition that connects Dewey to Montessori to the best progressive thinkers of our own time, involves a commitment to the whole child, to supporting genuine autonomy, to authentic collaboration, to deep understanding rather than surface coverage, and to the fundamental proposition that the people involved in any educational enterprise — including the children themselves — ought to have a meaningful voice in shaping it. That last point is where most schools, including many that call themselves Montessori, fall short. I will return to it.
Why It Has Always Been Hard
One of the more clarifying things Alfie said is that progressive education has never been the majority practice in American schooling. Not in Dewey’s heyday in the nineteen-thirties, not in the open classroom movement of the sixties and seventies, not now. When we ask what happened to the progressive schools, we are asking, in part, the wrong question, because the right question is perhaps: how do any of them survive at all, given the undertow that is always pulling against them?
Alfie laid out the structural reasons with real precision. Progressive education is more demanding of everyone it touches. It is more demanding of children, who are asked to be co-creators of their learning rather than passive recipients. Thinking from the inside out, grappling with genuine questions, collaborating rather than competing — these require more of a child than memorizing facts and producing them on a quiz. Children can coast on a traditional education in a way they cannot coast in a genuinely progressive one, and that reality produces its own kind of resistance.
It is even more demanding of teachers. You cannot fake deep content knowledge in a classroom where children are constructing understanding, asking unpredictable questions, and following the logic of ideas wherever it leads. A teacher who lectures can get by on superficial familiarity; a teacher who is genuinely facilitating children’s thinking cannot. Beyond content knowledge, progressive teaching requires profound pedagogical skill — an understanding of how people actually learn, not just what they are supposed to be taught. And it requires what Alfie described memorably as the ability to function more like a jazz musician than a recitalist: to be genuinely at ease with uncertainty, to follow the emergent shape of a lesson rather than the predetermined one, to give up control over things that most teachers hold tightly.
And then there is the broader social environment. Progressive education tends to produce critical thinkers, and critical thinkers are, as Alfie said, inconvenient for people in power. A culture addicted to competition and to standardized test scores as the measure of educational success will always be in tension with schools that measure themselves by other standards. Parents, even those who deliberately chose our schools, often exert pressure — sometimes subtle, sometimes not — toward the familiar. They know what school looked like when they were children; they know what the path to college is supposed to look like; they are anxious, and anxiety tends to push people toward convention.
The Standardized Testing Trap
I want to linger here, because Alfie was particularly incisive about the way standardized testing functions not just as a policy problem but as an epistemological one. The moment a school agrees to be evaluated primarily by standardized test scores, it has already conceded the most important argument. Those tests, as Alfie said, measure what matters least intellectually. High scores are not merely meaningless in themselves — they can be a warning sign, because of what had to be sacrificed, what had to be drilled and narrowed and decontextualized, to produce them.
For those of us in Montessori and independent schools, this might seem like someone else’s problem. We do not, most of us, live and die by standardized test scores the way a public school principal does. But the logic of standardized accountability has a way of seeping in regardless. It seeps in through parents who ask how your graduates perform on the ERB, the SSAT, or the ACT. It seeps in through the implicit conversation about college placement. It seeps in through any moment when we begin to ask whether our children are keeping up rather than whether they are genuinely learning.
Alfie’s point is that test scores become the default measure of educational success in the absence of a genuine community conversation about what we are actually trying to accomplish. And that is where the responsibility falls on school leaders. If we do not lead that conversation, if we do not bring parents and teachers and, yes, students into a shared articulation of what we are for, then the default will fill the vacuum. The default is test scores, college placement, and the anxious mimicry of whatever the most prestigious schools appear to be doing.
The Lever of Long-Term Goals
Here is the most practically useful thing Alfie shared, and I have been thinking about how to put it to work ever since. When he speaks to groups of parents or educators, he almost always begins by asking the same question: How do you hope your children will turn out? What are your long-term goals for them as human beings?
And the answers are remarkably consistent across constituencies that would seem to disagree about almost everything. People say, “I want my child to be happy.” Ethical. Caring and compassionate. Curious. Self-motivated. Creative. A genuine thinker. The consensus, Alfie observes, is striking, and it spans the ideological spectrum.
Then comes the pivot. He says, essentially: you tell me you want this. So why are you doing that?
Because the practices of traditional schooling — the drilling, the grading on a curve, the extrinsic rewards, the narrowing of the curriculum to what can be measured, the insistence on compliance rather than genuine engagement — are not only failing to produce these outcomes; they are actively working against them. A child who has been taught primarily to perform for external rewards is not becoming self-motivated. A child who has spent twelve years learning that the point of school is to get the right answer and move on is not becoming curious or creative. A child who has been ranked against peers since kindergarten is not necessarily becoming compassionate.
Progressive education, by contrast, is oriented toward exactly the outcomes that most adults, when they stop and think about it, genuinely want for children. Alfie described this as a kind of lever, and I think that is exactly right. As school leaders, we are often trying to defend our approach to people who are skeptical or anxious, and we sometimes make the mistake of arguing on our opponents’ terms — defending our test scores, justifying our college placement rates, translating our philosophy into the language of measurable outcomes. What Alfie suggests is that we can instead shift the ground entirely, by helping parents articulate their own deepest intentions and then making visible the connection between those intentions and what we are doing in our schools.
The complement to this, which Alfie also offered, is to ask people to look backward into their own schooling. When were you most alive in a classroom? When did you not want the bell to ring? The answers almost always point toward the features of progressive education: collaboration rather than isolation, genuine choice about what to explore, and active engagement rather than passive reception. Nobody says the best moment of my education was sitting quietly, taking a multiple-choice test. Help people see that connection, and you have a powerful ally in their own experience.
Systems and the Montessori Advantage
This is where I want to bring my own perspective into the conversation, because it is something my mother helped me understand and something I have been thinking about for fifty years.
John Dewey was a philosopher before he was an educator, and the school he created at the University of Chicago was a remarkable place. But as my mother used to say, his great limitation was that he did not think in terms of systems. The emergent curriculum at the heart of Deweyan progressivism — the idea that the curriculum should arise from the genuine interests and questions of children and teachers together — is a beautiful idea that is also genuinely exhausting. It works brilliantly when you have an extraordinary teacher, someone who can hold that emergent space with skill, depth, and endless creative energy. But it does not scale. It does not sustain itself across decades and generations. Schools that depend primarily on the heroic creativity of individual teachers burn through those teachers and then lose the thread.
Maria Montessori, for all the ways she can be (and should be) criticized and read selectively rather than reverentially, gave us something Dewey did not: a system. A coherent, refined, replicable system for creating the conditions in which children can genuinely flourish — the prepared environment, the three-year cycle, the trained observation of the teacher, the materials themselves as the embodiment of a philosophy. When I transitioned the Barrie School to Montessori, one of the most immediate differences I felt as an administrator was that teachers had a framework in place. They did not have to reinvent their professional identity from scratch every September. The philosophy was built into the environment.
This is, I think, one of the most important things we can say to school leaders who are trying to understand what distinguishes Montessori from other progressive approaches. It is not that Montessori is the only way to honor the child, the only way to support genuine learning, the only pedagogy with wisdom to offer. Alfie is right that we should borrow selectively from the tradition rather than treating any founder as infallible. But the systematization matters. It is what allows the work to outlast any individual practitioner, to survive the turnover among teachers, heads, and boards that is the reality of every school.
The caveat I would add is that systems can also become prisons. When AMI orthodoxy treats Montessori’s every word as scripture and treats deviation as heresy, the system that was meant to serve the child ends up serving itself. The goal of the system is always the child’s flourishing. When we lose sight of that, we have made an idol of our methodology.
The Voice of Children
I raised a question during the webinar that I have been thinking about, and I don’t think we have fully addressed it in the Montessori world.
We talk beautifully about Casa dei Bambini — the house of the children. But whose house is it, really? We prepare the environment meticulously, with great care and professional intentionality. We design the curriculum, select the materials, and set the schedule. And then we invite the children in to choose from among the options we have prepared for them. That is nothing; it is genuinely better than what most children experience in most schools. But it is also not the same as what Alfie and Dewey were pointing toward when they talked about children as co-creators of their educational experience.
Alfie put the question beautifully: Is the environment prepared for the kids, or with the kids?
At Montessori conferences, when children are present at all, they are usually performing — part of a musical, a presentation, a demonstration. They are not sitting alongside adults as partners in imagining what Montessori education could be. At AMI and AMS conferences, you do not find children on the program committee, or presenting research alongside their teachers, or challenging adults on decisions that affect them. And yet, at AERO conferences, which have always been a little hippie, a little rough around the edges, and genuinely alive in a way that more polished events are not, children run the thing. Children are speakers. Children are organizers. That is, to my mind, what a Montessori event ought to aspire to.
The practical implications of this for school leaders are real and immediate. When you plan for the new school year, can you invite your children — even your three-, four and five-year-olds — to help set up the classrooms? There is something profound and formative about a child who has cleaned every material with Murphy’s oil soap and set it on the shelf with care. That child knows this is her room, her house, in a way no amount of telling can convey. In Japan, children come to school two weeks before classes begin to prepare the building for the year. The school is something they have made, not something they have been handed.
At the adolescent level, the stakes are even higher and the failures more visible. If we believe that the prepared environment is the cornerstone of Montessori practice, then we ought to be asking ourselves what the prepared environment looks like for a fourteen-year-old and for a seventeen-year-old. Not what we have inherited from an elementary tradition stretched upward, but what a genuine Montessori secondary environment would be, designed around the developmental realities of adolescence, with meaningful student voice built into its architecture from the ground up.
Structure Is Not the Same as Control
The last thing Alfie said before he signed off was also, perhaps, the most useful for school leaders to carry into their daily practice. He said: ” Structure is not the same as control.
This matters because the false dichotomy that most educational conversation gets stuck in is between the authoritarian classroom, where the adult controls everything, and the laissez-faire classroom, where the adult steps back and the children are nominally free. Both of these are failures, and both are failures because they misunderstand the role of the adult.
Alfie’s position — and it is Montessori’s position, and Dewey’s at his best — is that adults have a critical and irreplaceable role in the learning environment, but that role is working with children rather than doing things to them or standing back while they flounder. Adults bring content knowledge, pedagogical wisdom, the ability to introduce ideas and experiences and possibilities that children might not have stumbled upon on their own. None of that is authoritarian. None of it requires that children be passive or compliant. The question is whether the adult’s authority is being exercised in service of the child’s genuine growth, or in service of the adult’s need for control, convenience, or the appearance of rigor.
When Alfie speaks about needing courageous leaders, he also pushes back on that framing in an interesting way. He is suspicious of the idea that the solution to our challenges is finding more individuals with grit and resilience and the willingness to put on iron underwear and take the hits from all sides. Not because courage is unimportant, but because focusing on individual courage is, in his view, a somewhat conservative strategy: it accepts the hostile structures as given and tries to breed humans who can survive them. What he would rather do is change the structures, build systems of progressive education that do not require heroism to sustain, that support good teaching rather than merely tolerating it.
I hear that, and I mostly agree with it. But I also think school leaders live in the real world, and the real world requires both: the long work of structural change and the day-to-day courage to keep doing what you believe in even when it is hard. We need people who are building better systems AND people who are willing to stand up in a board meeting or a parent coffee and say, this is what we believe, this is why it matters, this is the education your children deserve.
The Moment We Are In
I would be dishonest if I wrote this essay without naming the political context in which we are all working. Alfie said it plainly: public education, which he rightly called a cornerstone of a democratic society, is under assault in a way that is unprecedented in modern American history. The dismantling of federal education infrastructure, the defunding of public schools through voucher programs, the attacks on teachers’ professional autonomy and on the very idea that schools should serve the public good rather than private preference — all of this is real, and all of it creates the conditions in which good progressive education becomes harder to do and easier to attack.
Alfie’s point, drawing directly on Dewey, is that progressive education and democratic society are not merely related — they are constitutive of each other. A society that is becoming more authoritarian will, inevitably, put pressure on schools that are trying to cultivate democratic habits of mind, critical thinking, and genuine autonomy. The connection flows both ways: the work we do in our schools is not separate from the larger project of maintaining and renewing a democratic culture. It is part of it.
This is not a reason for despair. It is, I think, a reason to clarify what we are doing and why. When we protect the child’s right to be genuinely curious, genuinely heard, genuinely a co-creator of her own education, we are doing something that matters beyond the walls of our schools. We are preparing people who know how to think, who know how to question, who know their voices matter. In this particular moment in history, that is not a small thing.
What We Owe the Next Generation of Leaders
Alfie closed the conversation with something that has been sitting with me. He said he looks forward to the day when the average age of a group like ours is half of what it is now, because that will mean there is another generation ready to carry this forward. He was being gentle, but the point is real. Many of us who have been in this work for decades are at the back half of our professional lives. The question of who comes next, and how we prepare them, and what we leave them to build on, is not abstract.
What I think we owe them is honesty about how hard this is. Not discouraging honesty — the kind that makes young educators feel that the deck is so stacked against them that there is no point. But clear-eyed honesty about the structural realities, the institutional inertia, the social pressures, the genuine difficulty of doing progressive education well. And alongside that honesty, the clearest possible articulation of why it matters. Not the institutional version of why it matters, not the version that talks about college placement and differentiated instruction and twenty-first century skills, but the real version: because children are whole human beings who deserve an education that treats them as such, because democracy depends on citizens who can think and question and collaborate, because the moment when a child discovers that her mind is capable of something she did not know it could do is one of the most consequential things that can happen in a human life.
We were not wrong about this. The people who built the Barrie School were not wrong. Maria Montessori was not wrong, even when she was imperfect. John Dewey was not wrong, even when he was hard to read, and his Chicago school didn’t always follow through. The work is still the work. The question that Alfie’s presence always revives for me is whether we are doing it with enough urgency, enough clarity, and enough genuine partnership with the children who are counting on us to get it right.
Copyright 2026 The Montessori Foundation
