One big problem with Chesterton's Fence is that since you have to understand the reason for something before getting rid of it, if it happens not to have had a reason, you'll never be permitted to get rid of it.
That, and for certain kinds of fences, if there is an obvious benefit to taking one down, it's better to just take it down and see what breaks, then maybe replace it if it wasn't worth it, than to try and figure out what the fence is for without the ability to experiment.
My transformation begins with me getting tired of my own bullshit.
Katara: Do you think we'll really find airbenders?
Sokka: You want me to be like you, or totally honest?
Katara: Are you saying I'm a liar?
Sokka: I'm saying you're an optimist. Same thing, basically.
-Avatar: The Last Airbender
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A novice asked master Banzen: “What separates the monk from the master?”
Banzen replied: “Ten thousand mistakes!”
The novice, not understanding, sought to avoid all error. An abbot observed and brought the novice to Banzen for correction.
Banzen explained: “I have made ten thousand mistakes; Suku has made ten thousand mistakes; the patriarchs of Open Source have each made ten thousand mistakes.”
Asked the novice: “What of the old monk who labors in the cubicle next to mine? Surely he has made ten thousand mistakes.”
Banzen shook his head sadly. “Ten mistakes, a thousand times each.”
The Codeless Code