Humans have a complicated relationship with rules. 

One of the mantras of the 21st century economy is 'first, break all the rules'. If the rules are merely stale conventions, then yes: break away. But it's tempting to go too far and scoff at all rules, and even laws, as the petty creations of boring bureaucrats, declaring, "Rules? Pah! We won't be tied down by your rules!"

But it's not that simple. We like some rules, like the rule about not smoking in aeroplanes, or parking in your reserved parking place. When others break those rules, it's annoying. And rules that define boundaries can heighten, not hinder, creativity and impact — look at code golf, Yves Klein, haiku (though the 5–7–5 thing is a myth), and Twitter. 

So what to do about a rule we don't like? There are usually a few options:

1. Obey it. The rule worked! But maybe not for you.
2. Change it. This might work, but it might take a while. Good luck!
3. Break it. Easy! Just pretend it's not there. There's no need to feel bad: everyone else is doing it.

Is that it? Be boring, be brave, or stick it to the man? No, it's a false trichotomy. There is a fourth option:

In other words, don't break stupid rules — that doesn't change anything. Better to make your point by subverting the entire foundation of stupid rules. For example:

• When lawyer Larry Lessig decided he'd had enough of copyright restrictions, he didn't say 'screw you guys' and start downloading movies on BitTorrent. He started Creative Commons and transformed the way the sharing economy functions. Result: not just reduced revenue, but reduced impact of traditional media — far more important.
• The local government will partly fund training for small businesses from a marketing consultant. Apparently, it's common to game this system by hiring a consultant under this program, then simply having them do work for hire — website, branding, and so on. But these are normal business expenses; instead of coercing a broken system to channel public money into private enterprise, we'd all be better off beating a new path to small-scale investment and collaboration. 
• There's a young would-be Robin Hood in the geoscience publishing world, hosting copyrighted textbook PDFs for free download. He believes he's helping to rid the world of the tyranny of over-priced technical literature, but he's going about it the wrong way. Better to promote open-access literature, and be a champion of legal re-use. This denies 'the establishment' their impact, instead of lauding it, and helps spread truly shareable content.

Next time you come across a rigid rule you don't like, don't break it. Ask instead how you can make the rule not matter.