Learning Chinese as I am, I’m learning a lot of rules of that language. If you’ve spoken to me in person over the past few years, you’ve probably heard my fun-with-language game to purposefully conjugate the verbs to be and to have wrong. I often say “How is you?” or “I has to go to the store.”

I’ll be the first to admit the mis-conjugation is affected, but it’s also fun. Some friends have adopted it too and we make a game of it.

I mention the game now in the context of learning language to return to a concept I’ve written about before — what rules are, how to play by your own, and how fun making your own can be (illustrated with Calvin and Hobbes).

Breaking rules helps you understand their purpose and the motivations of who made them.

As an entrepreneur I’ve succeeded by breaking many rules, for example, to get meetings with people who normally only have time for people representing longstanding corporations. Same with getting myself exposure as an artist with negligible credentials from the art establishment.

Over the years I’ve learned to break rules more effectively, with fewer side effects I didn’t want or intend.

Breaking little rules like grammar helps you understand rules, how to break them, and the value of creating new ways of doing things. I recommend finding little rules to break and building from there.

(Never breaking rules, by the way, leads to 65-year-olds asking themselves what they achieved in their lives.)

What are rules?

When you start realizing why a given rule exists and what rules do, you start realizing why people follow them.

People tell others “You shouldn’t end a sentence in a preposition.” If I ask why, they tell me that it’s a rule.

So what? Who made that rule? When did I agree to follow it? Did you not understand me absolutely clearly?

Rules are people telling you what to do.

The person telling you the rule may feel like they aren’t tell you what to do, they’re just repeating a rule, which they think of as an absolute of the universe. But it’s not. Someone told them what to do, they followed, if they questioned the rule they didn’t see value in breaking it — more likely they didn’t realize they could break it — and now they’re telling you to do what they did.

In the context of grammar, I point out that the language they speak arose by breaking rules of older languages. If people before had followed those rules we’d be speaking old languages. But we don’t, so they must have, so breaking rules isn’t bad; it’s just different. You can create value with that difference.

Plenty of people end sentences in prepositions. We all understand them. I’m sure in the future that rule will disappear.

What happens when you break rules?

What happens when you break that rule?

Well, in this case everyone understands you anyway. You have to work hard to find a sentence where ending in a preposition makes it harder to understand than not. You often have to contort to follow the rule — who says “That’s the mountain down which I skied.”?

People who insist on following rules will shun you for breaking it. People who don’t care won’t. You’ll find yourself more welcome in some groups and not others. Get the pattern? Choosing which rules you follow chooses which social groups you join. Speak like a Harvard person and you’ll end up with Harvard people. Speak like a hip hop person and you’ll end up with other hip hop people.

Rules let you choose what groups you are a member of.

Fashion magazines give tons of rules of how to be fashionable. If you follow them fashionable people will like you. If you don’t, you won’t have fewer people liking you. You’ll have different people liking you.

Style magazines like GQ, Esquire, Elle, etc tell you tons of other rules, like how long your cuff should extend past the sleeve of your jacket or how not to shake a martini. Following enough of those rules will get you into the circle of people who read those magazines enough to follow those rules closely. You’ll surround yourself with great followers of those rules.

If you don’t follow their rules, you won’t have fewer friends, you’ll have different friends, most of whom follow different rules.

What can you achieve by breaking rules?

I’m much more interested in what happens when you break a rule intentionally and knowledgeably. I believe historical greats became great by knowing which rules to break when.

If you follow most of a group’s rules but break some in just the right way, so you signal you know the rule you’re breaking but want to do your own thing, you create the chance to show your style, your individuality. You can show greater mastery of the rules you’re breaking than someone following them.

You can create your own social circles.

The value of breaking rules

Isn’t that amazing? You can outdo people following rules by breaking them. For example, I haven’t read enough Esquire to know its rules so I can’t break them fluently. But I have enough Ivy League credentials that I can break some rules of grammar and nobody will think I don’t know so-called proper English. So I do and it creates a bond with friends.

Once I knew the rules of business enough I learned ways I could break rules of how to meet people and start meeting people well beyond who I had connections to. Some of my strongest and most mutually rewarding business relationships began with someone telling me I wasn’t supposed to contact them that way (sometimes they yelled it).

When I create my own rules, like mis-conjugating verbs, people who follow my new rules join my circle.

Try creating rules and see who follows your lead.

• ← Richard Feynman on fooling yourself not helping you
• Comparing biology and physics from a business leadership perspective →