One of the most dangerous moments in leadership occurs when we encounter a rule that appears to serve no purpose.

A few evenings ago, I was reading a recent The Atlantic article by McKay Coppins titled “Sucker: My Year as a Degenerate Gambler,” published March 12, 2026. It is an unusual piece – part memoir, part cultural commentary – in which the author immerses himself in the world of modern sports betting and emerges with a sobering reflection on its psychological pull and social consequences. 

Midway through the essay, Coppins referenced an idea that stopped me for a moment: Chesterton’s Fence. G. K. Chesterton, the early twentieth-century English writer and essayist, once described a simple situation. Two people encounter a fence erected across a road and blocking their path. One says, “I don’t see the use of this – let us tear it down.” The wiser of the two replies that they should find out why it was put there before deciding on a course of action.

We have addressed this simple principle before in the Circle of Leaders. Do not remove a rule, institution, or safeguard until you understand the problem it was originally designed to solve. Chesterton was not arguing that fences must remain forever. His point was that reform without understanding can be reckless. A structure that appears arbitrary or inconvenient may actually be the residue of a lesson learned long ago.

Reading that passage immediately reminded me of Admiral Hyman Rickover and the culture he created in the U.S. Navy’s nuclear propulsion program. Many of you will recall a related discussion during our recent episode of A CEO’s Virtual Mentor, where I had the privilege of speaking with Admiral Tom Fargo. In our conversation, we reflected on Rickover’s philosophy of leadership and operational discipline. Rickover understood something fundamental about complex organizations: procedures and safeguards rarely appear out of thin air. They are almost always the product of a prior incident, failure, or near-miss. 

What might appear to an outsider as needless bureaucracy is often something else entirely – the lessons of institutional memory. A safeguard exists because once, somewhere, it was absent. A verification step exists because once it was skipped. A reporting protocol exists because once an event went unreported. The rule is the lesson institutionalized. 

Over time, however, institutions face a predictable problem. The generation that experienced the failure retires. The story behind the rule fades. The context disappears. What remains is the inconvenience. “Why do we still have this?” asks a later generation. Without the historical knowledge, the fence begins to look arbitrary. And so the temptation arises to clear it away. 

This pattern appears in many domains – public policy, engineering, finance, corporate governance. Structures are created in response to real events: crises, accidents, frauds, collapses, or failures of judgment. Yet as the memory of those events fades, the safeguards themselves begin to appear unnecessary. 

Sometimes they are. But sometimes they are quietly protecting us from hazards that have not changed at all – ourselves. That was the broader point Coppins was making in his The Atlantic essay. As legalized sports betting has spread rapidly across the United States, the legal and cultural barriers that once surrounded gambling were dismantled with surprising speed. Yet few seemed to pause to examine the long history of social concern that produced those barriers in the first place.  

Whether one agrees with his conclusions or not, the reference to Chesterton’s Fence is a powerful reminder of how easily societies – and organizations – forget the reasons behind their own guardrails. Within the Circle of Leaders, this type of reflection is exactly what makes our community valuable. Ideas often emerge not from formal lectures, but from the intersection of reading, conversation, and experience. A passage in an article leads to a remembered principle. A principle connects to a conversation with a leader. A conversation leads us to reconsider how our own institutions operate. It is precisely these kinds of reflections – emerging from reading, conversation, and experience – that animate the discussions within the Lyceum Circle of Leaders. 

Many of the structures executives and board members encounter today – compliance frameworks, reporting requirements, safety protocols, governance procedures – can feel burdensome in the moment. Yet many of them exist because somewhere in the past an organization discovered, often painfully, what happens when they do not. 

It is a useful question to pose in any leadership team or boardroom: Why do we think this fence was originally built?  

That does not mean every fence should remain forever. Circumstances change. Institutions evolve. Some structures do outlive their usefulness. But Chesterton’s advice remains sound. Before removing the fence, understand the cliff it may have been built to keep people from approaching.