The LA Times called Kobe Bryant "the most polarizing figure in the history of L.A. sports." He spoke out against his team. He publicly quarreled with his teammate. These are transgressions that could end many people's career's, no matter how talented.

Yet Kobe leaves the game admired and supported.

Why can he break so many rules, yet exit so admired?

As entrepreneurs and leaders, the answer matters. We work in spaces where rules aren't as clear as in bureaucracies. We know we'll transgress sometimes. Many of business's most successful role models also broke rules in ways that created success.

It's not Kobe's on-court talent. His talent got him notoriety and kept him in the game, but players can be valued on the court and hated off it.

What are rules?

When you start realizing why a rule exists and what it does, you start realizing why people follow them. Let's look at a simple example.

People say, "You shouldn't end a sentence in a preposition."

"Why," I ask.

"Because it's a rule."

So what? Who made that rule? When did I agree to follow it?

More importantly, what happens if I break it? If I say, "That's the mountain I skied down," everyone understands me.

Rules are people telling you what to do.

They may feel like they aren't tell you what to do, they're just repeating a rule. Someone told them what to do, they followed and thought no more of it.

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?

In this case everyone understands you. No problem.

In most cases if you base your behavior on how you affect others instead of blindly following rules, you have to be more considerate, more empathetic, more thoughtful.

Wait. Kobe wasn't considerate, empathetic, and thoughtful. He may not have started that way, and his way of learning wasn't through the usual mindfulness path many think of, like meditation. But it was effective--a trial by fire that comes with living in the spotlight.

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.

Choosing the rules you follow chooses your social groups. 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.

Which rules you follow determines what groups you're in.

Jack Nicholson and rules

A friend who grew up in Queens and became the senior ball boy at the U.S. Open told me a story about Jack Nicholson there.

One day his friend was working at the door to the U.S. Open's VIP room, enforcing the jacket-and-tie dress code. Jack Nicholson came by and started walking into the room in shorts and a t-shirt.

Trying to enforce the rules, in a nervous high school student voice, he said "I'm sorry Mr. Nicholson. There is a dress code and I'm afraid I have to ask you to follow it."

With a polite laugh, Jack Nicholson said "I don't think so," and continued in.

The difference with Kobe, Nicholson, and successful rule-breakers

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

But they follow rules.

Their rules.

In fact, I'd wager the most rule-breaking people you can think of follow their own rules more closely. Some people's personal rules don't mesh with society's and get shunned.

Those whose rules do mesh with society end up more respected. Regular people only see the rules they're breaking, not the rules they're keeping.

The rest of the LA Times headline

The full LA Times headline I quoted above explains Kobe's public support despite breaking rules:

Kobe Bryant, the most polarizing figure in the history of L.A. sports, was always true to himself

He was always true to himself.

That's what to strive for. You get to learn about yourself when you do something you think is right independent of rules, others attack, and you realize you have to stick with what you think is right.

Two things that will lose people's respect:

First, if you only think of yourself, as Kobe did early on, then people will lose respect for you. His youthful transgressions forced him to consider others, as you must, if you want to succeed and make your own rules.

Second, if you back down from what you think is right, and what doesn't hurt others, then people will lose respect for you.

What to do about rules

Following rules blindly works for middle management and bureaucracy. Do it if that's your goal.

To lead and succeed in entrepreneurship, you will enter territory without rules. You'll have to live by your own. You will make mistakes. And that's how you learn: consider others with empathy and compassion and remain true to yourself when you do.