Chesterton's Fence: A Lesson in Second Order Thinking


In the ever-evolving world of technology, making changes to existing systems and configurations is a common occurrence. However, it is crucial to approach these changes with a mindful strategy, considering the long-term consequences. This is where the concept of Chesterton’s Fence and second order thinking comes into play.

Understanding Chesterton’s Fence

Chesterton’s Fence is a metaphorical principle coined by G.K. Chesterton, an English writer and philosopher. The idea behind the principle is to preserve and respect the existing structure or system until one fully understands the reasons behind its existence. Rather than haphazardly dismantling or modifying something, it is advisable to pause, investigate, and seek insights into the initial purpose of the structure or system.

The concept of Chesterton’s Fence can be seen in various domains, including software development, engineering, and even societal or political contexts. It serves as a reminder that rushing to change or removing something without fully understanding its purpose can lead to unintended consequences.

The Importance of Second Order Thinking

Second-order thinking goes hand in hand with Chesterton’s Fence. It is the practice of considering not only the immediate outcomes of our actions but also the consequences of those consequences. While first-order thinking focuses on immediate and simplistic reasoning, second-order thinking encourages a deeper examination of the potential long-term effects.

In the world of software development, second-order thinking is crucial for making informed decisions. It involves taking the time to understand the context, history, and implications of a particular configuration or code before making changes. In doing so, developers can avoid repeating mistakes, uncover hidden edge cases, and ensure the stability and reliability of their software systems.

Insights from User Comments

User comments shed light on the practical applications of Chesterton’s Fence and second order thinking. One user shared their experience in managing an AI service, emphasizing the importance of understanding the reasons behind existing configurations before making changes. They humorously referred to this process as “paying the Chesterton Tax.” By investigating the context in which a configuration was introduced, they could avoid unintended consequences and uphold the system’s integrity.

Another user highlighted the value of code comments to explain the rationale behind certain decisions. By communicating the why behind the code, developers enable future contributors to understand the original intent and make informed changes. Additionally, including breadcrumbs in comments and commits to relevant bug reports, documentation, or commits can help maintain a clear trail of reasoning.

However, there were also discussions about the potential pitfalls and misinterpretations of Chesterton’s Fence. One comment mentioned the danger of using it as a thought-terminating cliche to inhibit progress. It is essential to strike a balance between preserving existing structures and embracing innovation.

Another user cautioned against confusing humility with self-deprecation, highlighting the importance of accepting feedback without undermining one’s own expertise. Constructive criticism can lead to growth and improvement, but it is crucial to avoid self-doubt or downplaying one’s own capabilities.

Managing Edge Cases and Naysayers

User comments further discussed the topic of managing edge cases, both in software development and broader contexts. While some individuals may continuously raise edge cases to shut down conversations or assert their expertise, others view edge cases as valuable pressure tests for the design. Identifying and addressing important edge cases can strengthen the overall system, but it is essential to manage them effectively. Setting priorities, estimating likelihoods, and shelving non-essential edge cases can help maintain focus and prevent paralysis by analysis.


Chesterton’s Fence and second order thinking serve as valuable principles in making informed decisions and avoiding potential pitfalls. By respecting and understanding the existing structures and systems, we can navigate the complexities of technology and society more effectively. Incorporating second order thinking allows us to anticipate and address long-term consequences, improving the quality and reliability of our work. So, the next time you encounter a metaphorical fence, take a moment to investigate and consider the reasons behind its existence. Who knows? You may uncover valuable insights and avoid unintended consequences.


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