Chesterton’s Fence and Remote Work Policies: Why You Should Understand Rules Before Removing Them

Chesterton’s Fence and Remote Work Policies: Why Understanding Rules Before Removing Them Matters

When the pandemic forced millions of workers into their homes in 2020, many companies saw an opportunity. Why maintain expensive office space? Why enforce commute times? Why not simply delete policies that seemed outdated? But here’s what happened: some organizations thrived with remote work policies, while others discovered—too late—that they’d dismantled something essential.

Related: cognitive biases guide

This tension reveals a critical thinking skill that matters far beyond work-from-home debates: Chesterton’s Fence, a principle about understanding the reasons behind rules before changing them. It’s one of the most practical yet underappreciated concepts for knowledge workers navigating organizational change, career decisions, and personal growth.

I’ll walk you through what Chesterton’s Fence actually means, why it applies powerfully to remote work policies, and how you can use it to make better decisions about which rules to break and which to keep.

What Is Chesterton’s Fence?

G.K. Chesterton, the early 20th-century writer and thinker, articulated this principle in his essay collection The Thing. Here’s his original formulation:

In the matter of reforming things, as distinct from deforming them, there is one plain and simple principle… Do not remove a fence until you know why it was put up.

The metaphor is deceptively simple. Imagine you’re walking through a field and encounter a fence. It blocks your path. It seems pointless. You consider tearing it down. But Chesterton’s wisdom says: pause first. Ask why that fence exists. Who built it? What problem did it solve? Only after you can answer these questions—and only if you’ve verified that the problem no longer exists—should you remove it.

The principle applies because most rules, policies, and practices exist for reasons that aren’t immediately visible. Those reasons might be outdated. Or they might still be deeply important. The danger lies in assuming you know which is which without investigation (Clark, 2021).

The Remote Work Fence: A Case Study in Misapplied Removal

When I began researching how organizations handled the shift to remote work, I noticed a clear pattern: companies that thrived were those that understood why certain office-based policies existed before deciding to abandon them.

Consider the requirement that employees show up to the office. To the impatient reformer, this looks like an arbitrary rule—a relic of industrial-era management. But the fence existed for several genuine reasons:

• Spontaneous collaboration: Many breakthrough ideas emerge from unplanned hallway conversations, not scheduled video calls. The “osmotic communication” that happens in offices has measurable effects on innovation (Bernstein & Turban, 2018).
• Mentorship and knowledge transfer: Junior employees learn by observing senior colleagues. They absorb unwritten norms, ask quick questions, and build professional identity partly through physical proximity.
• Organizational culture: The office isn’t just a place to work; it’s a place where shared values, rituals, and social bonds form. New employees feel connected to something larger than their job description.
• Accountability structures: Managers could observe work patterns, respond quickly to problems, and maintain what sociologists call “social presence.”

None of these benefits are automatic. They require intentional design. Companies that simply erased the office requirement without building new structures to replace these functions discovered the fence was doing real work. They faced higher turnover, slower innovation, weaker culture, and isolated employees—especially those early in their careers.

Conversely, organizations that applied Chesterton’s Fence properly asked: “What was the office providing? How can we provide it remotely, or do we need to?” Some concluded that certain functions still require presence. Others built new systems: structured mentorship programs, intentional collaboration time, and cultural rituals that work online. These companies pulled down the fence thoughtfully, not carelessly.

Why Chesterton’s Fence Fails in Modern Organizations

If this principle is so useful, why do so many leaders, teams, and organizations ignore it? In my experience teaching professionals and observing workplace dynamics, I’ve identified three barriers:

First: The burden of explanation. Rules are often inherited. Nobody remembers why the onboarding process works this way, or why this meeting happens weekly, or why this approval step exists. The person who created the rule has left the company. Documentation is poor or nonexistent. When you ask “Why do we do this?” the honest answer is “I’m not sure.” This frustrates people and makes them feel the rule is arbitrary (Sunstein & Thaler, 2008).

Second: The assumption that new is better. We live in a culture that valorizes disruption, innovation, and breaking the status quo. There’s an implicit bias toward change. Keeping a rule requires justifying why you’re not changing, which feels defensive. This bias runs especially deep in technology companies and among younger workers, who’ve been trained to question authority and optimize everything.

Third: Visibility gaps. The benefits of a rule are often invisible until the rule is gone. The hallway conversation that sparks an idea? You don’t count it when you’re in the office—it feels like chitchat. But when remote work eliminates it, the absence becomes measurable as slower innovation. By then, the fence is already down.

These factors create a perfect storm for careless reform. A new manager arrives, sees a rule she doesn’t understand, assumes it’s outdated, and removes it. The real costs emerge months or years later, when they’re harder to trace back to the original decision.

How to Apply Chesterton’s Fence to Remote Work Decisions

So how do you use this principle practically? Here’s a framework I recommend to the professionals I work with:

Step 1: Identify the fence. Name the specific rule or policy you’re questioning. “Work from the office” is too vague. Better: “All employees must attend weekly in-person all-hands meetings” or “New hires work in the office for their first three months.”

Step 2: Research the origin. Interview people who’ve been in the organization longer. Ask the founders or long-tenured leaders: Why was this rule created? What problem did it solve? This isn’t always easy—institutions are often shaped by forgotten needs—but it’s worthwhile. You might discover that the rule addressed a real dysfunction or risk that’s still present.

Step 3: Test the problem statement. Assume the fence solved a real problem. Does that problem still exist? Has the context changed? For example: “Weekly in-person meetings existed because communication was bad.” But if you now have better tools and documented decision-making processes, the underlying problem may have evolved. Be specific: not “communication is better,” but “we now have Slack, decision logs, and async video updates.”

Step 4: Engineer the replacement. Rather than simply removing the fence, design what replaces it. The problem the old rule solved doesn’t disappear just because the rule does. You must create an alternative structure. If your weekly office meeting built team cohesion, a remote-work model needs something else: perhaps quarterly in-person retreats, intentional 1-on-1s, or different meeting structures. The point: acknowledge the work the old rule did and ensure something new does it (Bernstein & Turban, 2018).

Step 5: Measure and iterate. Monitor the outcomes that the original rule was meant to protect. If the fence kept certain risks at bay—turnover among junior employees, slow knowledge transfer, weak culture—measure these after you’ve changed the policy. Be willing to adjust if the outcomes deteriorate.

Chesterton’s Fence Beyond Remote Work

This principle extends far beyond work-from-home policies. In my experience, it’s one of the most useful mental models for any professional facing change:

Career moves: Before quitting a job, leaving a field, or changing roles, understand why you built the structure you’re in. Are you rejecting a career path because it’s genuinely wrong for you, or because you’re following fashion? Are you running toward something new, or away from discomfort?

Personal productivity systems: That morning routine, those blocking-out-time rules, that email policy—why do you have them? If they’re no longer serving you, by all means change them. But first, investigate what they actually do. Often we inherit habits without understanding their function, and we abandon them without noticing the consequences.

Organizational processes: Every process—hiring, approval chains, performance reviews, project management—exists because someone faced a problem. Before you streamline or eliminate, understand the problem. Maybe it’s solved. Maybe it’s evolved. Maybe there’s a better solution. But don’t assume the process is waste until you know what work it does.

The principle is really about intellectual humility. It’s about recognizing that if a rule has persisted, it probably persisted for a reason—even if that reason isn’t obvious to you. Not every rule is wise. Some are. Others are outdated or counterproductive. Chesterton’s Fence doesn’t say “never change anything.” It says “before you change, understand.”

Implementing This Thinking in Your Organization

If you’re leading a team or organization, here’s how to embed Chesterton’s Fence thinking:

First, document your rules. Not just the rule itself, but the rationale. Why does this policy exist? What problem does it solve? When should it be revisited? This creates organizational memory and makes future reforms more thoughtful.

Second, build a culture that questions thoughtfully. Encourage people to ask “Why do we do this?” but also to answer it. Make it okay to admit “I don’t know,” and commit to investigating. This is different from encouraging rebellion; it’s encouraging understanding.

Third, slow down reforms. Before you eliminate a policy, propose replacing it with something new. Run pilots. Measure outcomes. This isn’t bureaucracy for its own sake; it’s preventing costly mistakes.

Fourth, revisit decisions regularly. Set a schedule: every 18 months, review major policies and rules. Ask: Is this still needed? What would change if we modified it? This normalizes evolution while requiring intentionality.

Conclusion: The Wisdom of Constraints

Remote work is neither universally good nor universally bad. The office structure wasn’t purely oppressive, nor was it perfectly designed. The real insight is that both remote and office work are trade-offs, and the smartest organizations acknowledge the costs of each.

Chesterton’s Fence teaches us that rules, constraints, and structures are rarely arbitrary. They’re usually solving problems that aren’t immediately visible. When you’re tempted to remove a fence—whether it’s a work policy, a personal habit, or an organizational process—pause first. Understand why it exists. Verify that the problem it solved is truly gone or has been adequately replaced. Only then should you tear it down.

This approach takes more time than simply declaring “we’re going fully remote” or “back to the office.” But it produces better decisions, fewer regrets, and organizations that change with intention rather than fashion. In a world that moves fast and breaks things, that deliberate approach is increasingly valuable.

Sound familiar?

In my experience, the biggest mistake people make is

Last updated: 2026-04-01

References

1. Chesterton, G. K. (1929). The Thing: Why I Am a Catholic. Link
2. FunBlocks AI (n.d.). Chesterton's Fence. Thinking Matters: Classic Mental Models. Link
3. Business Analogies (n.d.). Business Analogy 055 – The DoorMan Fallacy – Chesterton's Fence. Substack. Link
4. Hacker News Community (2024). AI-generated “workslop” is destroying productivity? Hacker News. Link
5. Davidson, T. (n.d.). Research notes on AI transition and Chesterton's Fence. Referenced in EA Forum. Effective Altruism Forum. Link

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