The Ouroboric Gag, Part V

High-Entropy Institutions and Binding Possibilities

Author’s Note: I will be presenting on “Navigating the Metacrisis” at the Southern Association of Independent Schools’ Annual Conference this fall (Chattanooga, Oct. 4-6), and I am hopeful that my proposal for a 3-hour workshop at the National Association of Independent Schools’ Annual Conference (Baltimore, March 3-5) will be accepted. If you’re heading to the SAIS conference and want to connect to discuss the topics in this series further, please let me know.

“It is difficult to get a man to understand something, when his salary depends upon his not understanding it.” - Upton Sinclair

This is one of the driest seasons on record in my county. The drought is bearing down on our farmers—some of whom send their children to my school. Compounded with rising diesel prices, the burdens on our agricultural system are intensifying. Downed trees left by Hurricane Helene in 2024 served as kindling for wildfires in Georgia and Florida this spring; the smoke from those fires drifted north and settled over our regional track meet a few weeks ago, a looming reminder of our atmospheric interdependence. We are receiving more official visits from families that are relocating to my small town from Charleston—pushed out by overcrowding and an infrastructure that can no longer absorb its own growth—and while their arrival is a conventional enrollment win for my school, I find it difficult to receive it as simply good news: Does anything good emerge when a place, a person, or a system is stuffed to capacity? In the South Carolina State House, the fight over redistricting is just beginning, straining racial tensions that were never far from the surface. And because we are located next to Shaw Air Force Base and serve many military families, several of our parents are actively deployed, which means military spouses and students are coping with significant stress and concern. Former Presidential candidate and still tech entrepreneur Andrew Yang recently reported, “I just came from an AI conference out west, and holy cow! They said to me that what we’re going to see in the next six months outstrips what we’ve seen in the last ten years.” His enthusiasm is an ornament for the ed-tech wars that are escalating in reaction to tech and smartphone bans and the backlash and scapegoating screens have received in the wake of damning and correlative evidence, evidence that our young people are suffering emotionally, physically, and cognitively like no other modern generation before them, because their lives are constantly mediated by screens.

War. Energy constraints. Drought. Wildfire smoke. Overcrowding and infrastructure strain that will inevitably degrade the environment and the local economy. Political polarization deepening in my state legislature and leaking into local communities like a toxic gas. And looming technological disruption and infighting.

This is the Metacrisis—not as an abstraction, but as the weather of daily life in one small town in the American South. And as I have argued throughout this series, these crises do not arrive independently. They emerge from the same ontological foundations: the belief in infinite growth on a finite planet, in separateness from the ecosystems that sustain us, in linear “progress” that need not account for what it consumes. You might reasonably observe that the world has always known war, drought, and political conflict. What is different now—what makes this a genuine civilizational inflection point rather than another difficult season—is the speed at which these crises are compounding and the intimacy with which they are entangled. They are not separate problems awaiting separate solutions. They are one problem wearing many faces. But this is a hard reality to swallow.

Beyond the Local

And if you’ve been paying attention to world events, especially around energy flows and constraints, you should be seeing the metaphorical rats emerging from the sewers, and energy disruption is a foundational driver of the Metacrisis. We have faith in a fragile and terminal energy system, and its fragility is being exposed by the closure of the Strait of Hormuz. Countries around the world are imposing significant consumption controls to brace against and adjust to the reduction in energy supply. And while the United States is poised to absorb the shock because oil will flow to the highest bidder, we are still projected to suffer financial pain that will likely result in (at minimum) self-imposed limits this summer.

As a leader in an independent school, how are you preparing for this potential shock to the system? How many families are already stretched to the absolute max to afford your tuition, tuition that, for reasons within and beyond your control, continues to significantly increase to serve the Abundance Model that has become the fundamental, default strategy for independent schools?

Can you absorb 10 full-pay families leaving this summer because their budgets are stretched thin and they begin to cut non-essentials? Is there a strategy in place to signal to these families that you will weather this storm together? And does your CFO know about it? What discussions have you had with your Trustees about this energy disruption—would they listen? Is this potential strain on their radar? How can you have a reasonable response prepared if these predictions manifest—without causing panic in your community? And what if this temporary storm becomes a permanent feature?

As I argued in the last post, by way of Camus’s The Plague, denial of our reality is our first reflex. This crisis in Iran will be over quickly. The situation is too complicated for me to understand. It’s the summer anyway, and no one wants to hear from the school. The information I am receiving is unclear, and without certainty, I don’t want to look foolish. I am not an energy expert—this conflict is too far afield. I can always react if necessary since no one else is going to say or do anything (culpable deniability). I will pray for peace in my time, and leave this mess for my grandchildren.

I understand denial. I am, we are all, complicit. We have to do better.

When navigating the Metacrisis, certainty is a fool’s errand. Confusion is more honest. But clarity is the goal. We know our economy runs on an illogical premise—that we can have infinite growth on a finite planet. The lifeblood of this infinite growth has been cheap, reliable energy, energy that we have pilfered from the depths of the earth, energy that is not a “naturally occurring mineral substance that exists in endless abundance at the earth’s deep interior like the creamy nougat center of a bonbon.”¹ There is an end date that our extraction rate guarantees (peak and then decline, eventually), but in the meantime, any disruptions will have a direct impact on our operational budgets, not to mention capital campaigns, and will test our sustainability.

The International Energy Agency is calling the closure of the Strait of Hormuz the largest disruption to global oil markets in history, and whether we agree or disagree with that assessment, we all can recognize that the proliferation of cheap and powerful fossil fuels has directly supported the halcyon days of independent schools since at least the 1980s and has significantly contributed to the way we think about strategy and sustainability—more is better, more is safer, more is guaranteed.² The irony is that we have taken this gift of nature and industry and built “high-entropy institutions” (see below) that rely on cheap and abundant oil to sustain themselves. So when that energy source is significantly disrupted, or when we reach peak oil—whether that is soon or fifty years from now—without a sufficient alternative, independent schools will be forced to contract and simplify.³ This is where it’s all eventually heading.

Understanding the illogical nature of our economy and our implicit belief that cheap, abundant energy is endless can bring clarity to this current disruption. And I understand the hesitancy to jump to conclusions; our current US oil reserves are being used to offset the reality of our situation, so yes, a little more cost at the gas pump is not the end of the world, and we may be ok this time. But my question is, as a leader of a non-profit, tuition-driven school (at least for most independent schools), are you paying attention to this shift? And are you connecting our economy’s reliance on oil with your school’s “progress”? Without cheap, reliable fossil fuels and the excess wealth and resources they supply, how would our schools look? When do we begin to reimagine our long-term strategy, knowing the oil tap will eventually sputter and then run dry?

High-Entropy Institutions

I have written before, quoting from Hartmut Rosa’s The Uncontrollability of the World, that independent schools are dynamically stable institutions—we require “constant economic growth, technological acceleration, and cultural innovation in order to maintain [our] institutional status quo.” Every head of school knows the feeling: the budget meeting where nothing can be cut because everything is load-bearing, the strategic plan that adds initiatives without ever retiring them, the capital campaign that funds buildings whose operating costs will strain the next generation of trustees. We are generating excitement and “innovation” around addition, which, because nothing can be dropped, feels like the only possible way forward to justify our tuition, tuition that significantly increases because “everything gets more expensive” in an economy that is based on abstract as opposed to real value.

This is what a high-entropy institution feels like from the inside—not corrupt, not mismanaged, just irreversibly complicated, dependent on inputs that were never guaranteed and are currently at risk. When cheap fossil fuels become scarce, the strategy of dynamic stability will fail.

And maybe that’s ok.

Our dynamic stability, our high-entropy institutions, are producing negative by-products: overscheduled students internalize the institution’s logic and conclude that rest is falling behind; anxiety, depression, and burnout follow. Honor code violations increase not because character has collapsed—which is the criticism from the adults in the room who are perpetuating the system—but because a system that is simultaneously high-stakes and unsustainable makes cutting corners feel like survival rather than sin. Teachers, consumed by the complexity of managing an ever-expanding institution, drift from the relational work of genuine development toward the administrative work of performance coordination. And at the institutional level, mission becomes increasingly difficult to locate beneath the accumulation of programs, demands, and commitments that no one remembers choosing but everyone is afraid to remove. The high-entropy school does not fail dramatically—it hollows out quietly, measuring its health in, often superficial, outputs. At the same time, the people inside it absorb costs that never appear on the balance sheet.

Here is what those costs actually look like from the inside of a classroom. The learning scientist and educator Carl Hendrick, drawing on Herbert Simon’s The Sciences of the Artificial, offers an image worth sitting with: an ant making its way across a “wind-swept beach” traces a path of immense complexity—twisting, looping, zigzagging.

In his 1969 book The Sciences of the Artificial, Herbert Simon invites us to consider an ant making its way across a wind-swept beach. If you were to trace its path, you would see a line of immense complexity: it twists, loops, zigzags, and detours. Watched long enough, you might be tempted to attribute this complexity to the ant itself, to assume it possesses a sophisticated internal navigation system or a complex strategy.

But Simon argues this is a fundamental error. The ant is simple; it is the beach that is complex. The ant has a simple goal (get home) and simple rules (go around the pebble, climb the dunelet), but the complexity of its behaviour is merely a reflection of the complexity of the environment it must navigate. Simon’s radical hypothesis is that human beings are exactly like that ant.

As Hendrick notes, “The implications of this are profound, and cut against much of what we assume about learning. If behaviour is shaped by environment, then the quality of the environment determines the quality of the behaviour. A chaotic beach produces a chaotic path. A cluttered task produces cluttered thinking. And here is the crucial point: natural environments are not optimised for learning. They are optimised for nothing at all; they simply are” (emphasis mine).

And here is what the high-entropy school has done: it has replaced the right kind of artificial difficulty—the designed cognitive struggle that produces genuine understanding—with the wrong kind: the bureaucratic complexity, the overscheduled busyness, the performance anxiety that produces credential accumulation without authentic, genuine development. We speak endlessly to the ant. We exhort students to try harder, to believe in themselves, to develop a growth mindset. We send teachers to courses about resilience. We put up posters about famous people who overcame adversity. All the while, the beach remains as it was: windswept, cluttered, and indifferent to the learner’s good intentions.

The ant does not need a better attitude. It needs a better beach, as Hendrick argues.

High entropy is not merely an operational problem. It is the structural precondition for the Abundance Model, and it, alongside the gravitational pull of Molochian forces, forecloses the very reorientation toward human development that this series has been arguing is necessary. To make that shift, school leaders face the real possibility of total collapse; it is daunting to entertain the real metabolic costs to leaders, teachers, parents, students, and trustees to dismantle load-bearing systems, reorienting them toward human development, toward systems that account for how humans produce meaning, build healthy communities, and live with real constraints, while simultaneously keeping the school running—which is not to say that it is impossible, just monumental.

The exit from dynamic stability—and Molochian forces—cannot be willed by individual leaders working alone; it requires coordination, constraint (i.e., wisdom), and what I have been calling, throughout this series, binding mechanisms.

How Do We Bind Ourselves, Our Schools?

In light of my claims, it shouldn’t be surprising that we are witnessing a return to spiritual practices—whether that’s mindfulness and meditation, prayer, or returning to church. There’s disagreement about how widespread this movement is, so I will speak about the shift as a principle: we are tired of abundance, of being saturated in the fat of an oil economy, of numbing ourselves with every pleasure humans might reasonably desire—and many not so reasonable. I believe we are desperate to stop, but we don’t know how. And like I said above, shifting toward a more sustainable and ecologically bound way of life—much less a way of educating—will be so metabolically expensive as almost to be impossible.

I think about the scene from the 2002 movie, Catch Me If You Can, when the young con man, Frank Abagnale Jr. (played by Leonardo DiCaprio), returns home to tell his dad, Frank Sr. (played by Christopher Walken), that he’s getting married. On top of that, he assures Frank Sr. that he’s getting everything back that the IRS took from their family—the house, the Cadillac—and that when his mom sees that everything is restored, she’ll return, and the family will be together again. Frank Sr. tells his son that his mother has remarried and won’t speak to him anymore.

Frank Jr. can’t believe it. All of his crimes have been bent on the purpose of bringing his family back together. His response, then, is redemptive—“Dad, it’s over,” he says. But Frank Sr., who may best represent that tired, Baby Boomer generation, some of whom will die believing that the consequences of our industrialized, suburbanized world will never catch up to us, says, “They’re never going to catch you, Frank.” He’s like the “final guest” at the end of The Great Gatsby “who had been away at the ends of the earth and didn’t know that the party was over.”

Seeing his son visibly flustered about his mother’s “betrayal,” Frank Sr. gently pleads, “C’mon, sit with me. Have a drink. I’m your father.”

“Then ask me to stop. Then ask me to stop,” Frank Jr. begs.

This is the call for binding that I believe we are so desperate for today: an authority figure to set the limits, to tell us it’s ok to slow down and simplify. That we are right to be burned out, exhausted, and in need of renewal, of a different path.

Frank Sr.’s response, “You can’t stop”—this is the message that dynamically stable and high-entropic institutions whisper into our dreams at night.

Though I am not a Freudian or Jungian philosopher, one can’t help but see that the father, this patriarchal force, is encouraging young Frank’s arrested development, a life free from responsibility and wisdom. In his perversity, Frank Sr. would rather watch his son destroy his life than admit to his own culpability and irresponsibility as a father—he had not taught his son how to live with boundaries. And we continue to see this failure today in our elders, who would scapegoat anything (technology, lax morals, work ethic, MTV, etc.) before they admitted that their reliance on fossil fuels and abundance—a reliance that has decimated our ecosystems, our local communities, our families—was wrong, was ill-advised, was unwise, for all the good gifts it did bring.

We need the return of the mother, the maternal, to explore a different direction, one of sustainability and boundaries. And wherever this spiritual return goes, where we need to land is on the realization that we have everything we need. The research on human development is ample and accessible. We know what children need: stable relationships, genuine challenge, time to be bored, adults who model integrity. None of that requires a capital campaign—or anything additional to the faculty and staff in the room.

A spiritual revolution has the power to bind us (“religio,” the Latin root of religion, means “to bind”), but because we understand the power of Molochian forces and how our economy exploits our biological desires for short-term wins, we need to combine a spiritual evolution with concrete binding mechanisms.

The mechanisms I explore below are not the only routes toward binding. Part VI addresses the most obvious one—and the most seductive: the mission statement. But the following deserve attention first, precisely because they are less examined, though these routes are some of the same ones that have supported the Abundance Model.

Examples of How to Bind Independent Schools

And here is where Audre Lorde's warning must be held in mind: “The master's tools will never dismantle the master's house. They may allow us temporarily to beat him at his own game, but they will never enable us to bring about genuine change.” The mechanisms I am about to describe are, in many cases, the master's tools. They were built within the same system they are meant to reform, and that contradiction is real. I name them anyway, because the exit from dynamic stability cannot wait for a perfect instrument—and because knowing a tool's limitations is the beginning of using it wisely.

501c3 Status

The tax-exempt status granted to independent schools under Section 501(c)(3) of the Internal Revenue Code is perhaps the most invisible binding mechanism in the sector—invisible because it is so foundational that it has ceased to feel like a choice. In exchange for their exemption from federal income tax and the deductibility of donor contributions, independent schools are required to operate exclusively for public benefit. This is the legal commitment: not to their current families, not to their endowment, not to their competitive position in the marketplace, but to the public good.

In practice, this commitment is almost entirely unenforced. There is no federal requirement that an independent school demonstrate meaningful public benefit beyond the act of education itself—no minimum financial aid threshold, no community access requirement, no metric by which the IRS evaluates whether the institution’s operations serve anyone beyond its existing constituency. Is the town or city you exist in being served by your existence? How? In what ways, specifically? Schools self-report. To my knowledge, accrediting bodies do not audit public benefit. The result is that 501(c)(3) status functions less as a binding constraint than as a tax advantage—the public subsidy without the public accountability.

This is worth naming clearly: independent schools receive significant government forbearance—freedom from property taxes on campuses that are sometimes worth millions of dollars, freedom from federal income tax on operating surpluses, and the benefit of donor deductibility that subsidizes fundraising—while bearing almost no enforceable obligation to the public that forgoes that revenue. The “independence” of independent schools is, in part, publicly subsidized (more on the delusion of independence later).

Could 501(c)(3) status become a genuine binding mechanism? In principle, yes—if accrediting bodies or state attorneys general, who have jurisdiction over nonprofit compliance, required schools to demonstrate public benefit through measurable commitments. There are many problems with this suggestion, I recognize, but it’s worth exploring. If independent schools were bound to serve their local communities in new and meaningful ways (i.e., not just offering community service volunteers at the local festival, which is fine, but not what I am suggesting), then it’s possible to imagine independent schools orienting toward civic virtue, sustainable local economies, or solving local challenges like urban renewal (In Part VII, I will explore how this shift would disrupt the current architecture of our independent-school networks in productive ways).

Accreditation

Accreditation is the mechanism that most closely resembles what a genuine binding institution could be. Regional associations visit schools on a multi-year cycle, evaluate them against published standards, and grant or withhold the credential that gives schools their legitimacy in the eyes of colleges, families, and peer institutions. In principle, this is exactly the kind of binding mechanism the series has been calling for—an external authority that closes certain Molochian offers, holds schools accountable to shared standards, and removes the competitive pressure from individual decisions.

In practice, accreditation has become something closer to a compliance exercise than a genuine accountability structure. In my experience, the standards are process-oriented rather than outcome-oriented—they evaluate whether schools have the right documents, the right committees, the right self-study procedures—without asking whether those processes produce what they claim to produce. A school can receive full accreditation while its students are measurably more anxious, its teachers more burned out, and its reason for being more opaque than when it was last visited. Accreditation measures institutional health the way a mission statement describes institutional purpose: aspirationally, abstractly, and without binding consequence for the gap between claim and reality.

More fundamentally, accrediting bodies are membership organizations—funded by the dues of the schools they accredit. This creates a structural conflict of interest that is rarely named: the accreditor depends financially on the continued membership of the accredited. I am told that sanctions are rare, that withdrawals of accreditation are rarer still—maybe it happens more than I am aware. The incentive structure pulls consistently toward affirmation rather than accountability. How can we restructure this system to provide the type of “teeth” we need in the accreditation system to bind us? What would genuine accreditation look like?

It would evaluate outcomes, not processes. It would measure student development across dimensions that matter—not just college placement rates but longitudinal wellbeing, civic engagement, and the capacity for meaningful adult relationships (some of this does come up in the self-study). It would require schools to demonstrate coherence between mission and practice, not just the existence of a mission statement. And it would be funded independently of the schools it evaluates. None of this is technically impossible. All of it would require the sector to accept accountability, which it has so far successfully avoided.

Endowment

The endowment is the most powerful and least examined binding mechanism available to independent schools—powerful because it represents the accumulated capital of an institution’s history, and least examined because its governance is almost entirely internal. Unlike 501(c)(3) compliance or accreditation, which involve at least nominal external accountability, the endowment is managed by the board of trustees with minimal outside oversight.

This matters for two reasons. First, the endowment is the institution’s primary buffer against market pressure—a well-endowed school can, in principle, make decisions that serve long-term human development rather than short-term enrollment pressure because it does not depend entirely on tuition revenue for operational survival. It can say no to things that poorly endowed schools cannot afford to refuse. In this sense, endowment is genuine independence—the financial capacity to honor a mission when the market pulls against it. The question is whether schools use it that way.

Most do not. Endowment draw policies are typically set at 4-5% annually and treated as a floor rather than a ceiling—a supplement to operations rather than a source of strategic courage. Boards that could use endowment resources to subsidize tuition for a broader range of families, to fund teacher compensation at levels that reduce turnover, or to deliberately cap enrollment in service of relational density instead use those resources to fund the next capital campaign, the next building, the next program that signals competitive advancement. The endowment, in other words, is captured by the same Abundance Model logic that it could theoretically resist.

A genuinely binding use of endowment would require boards to ask a different question than “how do we grow the endowment?” The question would be: “what decisions would we make differently if we were not dependent on next year’s enrollment?” That question is rarely asked. When it is, the answers could be transformative, could lead to the type of renewal we need.

Eight-Year Study (NAIS)

A shout-out to my friend Denny Blodget for this suggestion. Also, see Sam Chaltain’s recent Substack post about this research.

There is a historical precedent worth remembering. Between 1932 and 1941, the Progressive Education Association coordinated what became known as the Eight-Year Study: thirty secondary schools, freed by agreement with three hundred colleges from standard admission requirements, redesigned their programs around genuine human development rather than credential production. The results were favorable and consistent—graduates of the participating schools outperformed their matched peers on multiple measures of intellectual and civic development, with the biggest differences appearing among students from the most experimentally ambitious schools. The study did not fail. It was overtaken by history and then quietly buried by the postwar credential economy that reasserted the very logic it had suspended.⁴

NAIS exists, in part, to do what the Progressive Education Association did in 1932—to coordinate action that no individual school can take alone. The question is whether it has the institutional courage to use that capacity. A contemporary Eight-Year Study would not require revolution. It would require NAIS to convene a willing cohort of member schools, negotiate with a consortium of colleges to waive standard admission requirements for their graduates, and commit those schools to a documented alternative framework for human development—one grounded in what we actually know about how adolescents grow, rather than what the market rewards. The colleges that would be most receptive are not hard to identify. The schools willing to try are not hard to find. What is missing is not the possibility. It is the coordination.

This is what real binding looks like in practice: not a mission statement, not an accreditation checklist, but an agreement among enough parties to close a specific offer—the offer Moloch has been making to independent schools for forty years.

A Better Beach

Each of the mechanisms above—501(c)(3), accreditation, endowment, a contemporary Eight-Year Study—addresses the institutional architecture around learning and programming. But none of them answers the question of what learning itself should look like once the Abundance Model’s pressure is reduced. That is where Herbert Simon’s thinking, and Carl Hendrick’s extension of it, becomes helpful.

Simon’s ant does not need motivation. It needs a better beach. The implication for schools is precise: the problem is almost never the student’s internal state. It is almost always the environment we have built. And here the Abundance Model has done something particularly damaging—it has confused the wrong kind of difficulty with the right kind. High-entropy institutions are full of difficulty: the pressure of accumulating credentials, the anxiety of competitive positioning, the exhaustion of perpetual motion. But this is not the difficulty that produces the types of adults who will be charged with the task of “hospicing modernity” and reimagining what it means to thrive in a post-fossil fuels glut. It is the difficulty that produces burnout. It is anti-healthy human development.

What we need, then, is not, in Hendrick’s terms, less artificial learning but better artificial learning—environments designed with genuine care for how cognition actually works, for how healthy human development happens, for how people live in and thrive in local communities, for how we have a sustainable relationship with our ecosystems, and for how we prepare young people to live well within limits rather than in defiance of them.

If you are a head of school, a teacher, a trustee, or a parent reading this and feeling the weight of recognition—that uncomfortable sense that this describes your institution, your decisions, your daily compromises—I want to say directly: that recognition is not guilt. It is the beginning of clarity. And clarity, however costly, is what we owe the children in our care.

The question is not whether independent schools have the structural latitude to respond differently—they do, more than any other sector of education. The question is what conditions would make that independence operational rather than rhetorical. For that to happen, we need more binding.

Part VI turns to the binding mechanism that ought to be the most obvious: the mission statement.

1. James Howard Kunstler, The Long Emergency: Surviving the Catastrophes of the 21st Century.

2. This is a bold statement, perhaps, but all I am really saying is that the excess produced by an economy based on cheap and accessible fossil fuels has led to the abundance we currently see in independent schools. The history of that impact is harder to pin down and would be a great research project.

3. That “alternative” comment is a little loaded. We have hope that “science and technology will save us,” one of our ontological hallucinations from my last post, and the hope for “alternative energy sources” that will replace our current reliance on fossil fuels may be a fool’s errand. There are plenty of ideas: nuclear (fusion, fission), wind, solar, etc. But none may prove as powerful and as efficient as the fossil fuels we currently enjoy. In short, we need to get comfortable with the idea that no matter what, in Nate Hagens’s terms, the great simplification will happen.

4. Watras, J. (2006). Education Policy Analysis Archives, 14(21).