First, I see that quote as mocking both sides, it seems more like Chesterton was trying to be an enlightened centrist. To boil it down, his quote is basically "

First, I see that quote as mocking both sides, it seems more like Chesterton was trying to be an enlightened centrist. To boil it down, his quote is basically "Progressives make new mistakes, conservatives keep repeating old mistakes". And I always felt Chesterton's fence to be advice to be deliberate in your actions. Spending the time and effort to find out why the fence exists, doesn't mean it won't get torn down. It just means that we won't be taking it down spontaneously.