The person that most effectively breaks the rules is the person that understands the rules flawlessly.
In order to customize, modulate, or personalize within a system effectively, you have to know that system better than anyone. You don’t want to end up with a Chesterton’s Fence scenario, where you’re breaking rules that you don’t understand, because sometimes those are load-bearing rules and you’ll bring a world of pain down around yourself.
Here’s a classic example that I witnessed the other day: I was driving on a highway that was several lanes wide. Traffic wasn’t bumper-to-bumper, but it was slow. The far right lane, however, was wide open. So a particularly impatient driver swerved into that lane and sped up – only to nearly rear-end the police car that was occupying that lane, guarding construction just beyond it. (The problem with particularly low-to-the-ground sports cars is that they really limit your visibility in traffic.)
A more reasonable person might have looked at the empty lane and said, “yes, I can’t see an obvious reason why no one is spreading into this lane, but the fact that no one is suggests that there may be a non-obvious reason, and I should wait until I have more information.”
That’s an example of someone who flaunted the rules of a system without fully understanding them.
Now, if you’ve read any sampling of posts on The Opportunity Machine, you know that I’m no fan of rules and I recommend testing them thoroughly and breaking as many as you can get away with. But that “get away with” part is important, meaning that you need to fully understand the consequences of what you’re doing. I hate rules, so I study them constantly. Only a fool would, as a consequence of despising rules, ignore them. I break rules aplenty, but I never ignore them.