Issue #1 Challenge: Spot Your Own Chesterton’s Fence

December 4, 2025The Purple People Leader

You’ve read the manifesto and explored Chesterton’s Fence – the principle that before dismantling any idea, policy, or tradition, we must understand why it exists. Now, it’s your turn to apply it. This quick challenge is your first workout in independent thinking. No right answers, just a pause to question assumptions. It takes 5-10 minutes and will sharpen your lens on the world.

Why This Matters for Purple Thinkers

In our polarized discourse, we often react to surface problems without digging into roots. Chesterton’s Fence builds empathy: It asks, “What purpose does this serve?” and “What might break if I remove it?” For the Frustrated Centrist or Curious Skeptic, this counters knee-jerk extremism with deliberate reflection. Let’s practice on something personal or topical.

Your Challenge: Identify and Interrogate a Fence

Pick one “fence” from your life, news feed, or debates. It could be a policy, habit, or belief. Follow these steps:
1. Spot the Fence: Name it. Examples:
• A workplace rule that annoys you (e.g., “mandatory meetings”).
• A social norm (e.g., “cancel culture” in online debates).
• A current event (e.g., debates on social media regulations – why the broad free speech protections?).

Your turn: Write down one fence that’s bugging you right now.

• Ask the Why: Research or reflect on its origins. What problem was it built to solve?
◇ Tip: Quick Google or recall history – What issue was this rule or idea meant to fix?
Example for meetings: “It might have started to stop mix-ups in teams working from home after the pandemic hit.”
◇ Avoid: Jumping to “It’s stupid, tear it down!” Instead: “What unintended harm might come from removing it?”

• Weigh the Trade-Offs: Pros/cons of keeping vs. changing.
◇ Pro: Stability, lessons from the past.
◇ Con: Stagnation if outdated.
◇ Exercise: Jot 2-3 bullet points for each side. How does this foster humility?

• Reflect and Share in the comments if you’d like: What surprised you? Did it change your view? This builds the intellectual muscle for future formats like the Ideological Turing Test.

Bonus: A Quick Intellectual Humility Check

Rate your initial reaction to the fence on a scale of 1-5 (1 = “I’d demolish it immediately,” 5 = “I paused to understand first”). If it’s low, that’s okay – awareness is the first step. Our Uncertainty Index (coming in Issue #5) will dive deeper into embracing ambiguity.
What fence did you choose, and what did you learn? Drop it in the comments below, let’s discuss as a community. Your insights might inspire future issues!


– The Purple People Leader Team