On Breaking the Rules


I was taking a business trip to Hartford when it happened. I had ignored the flight attendant’s instructions to put away my laptop properly. I was sitting in row one by the window, so there was no storage. My only option was to put the laptop in my backpack in the overhead compartment. But instead, I decided to keep the machine with me, cleverly hidden from the flight attendant’s view – stuffed in the thin space between my seat and the airplane wall. Sneaky and convenient. Thank you Apple for making the MacBook Air so slim!

We took off and the plane tilted upwards. It took a second, but I finally thought about my laptop. I reached down to grab it thinking it was in danger of sliding backwards away from my seat. Too late! I didn’t feel it. I bent over and couldn’t see it either. Panicked, I then committed one of the worst airplane sins imaginable – I unbuckled during takeoff and half stood up. I asked the man in the seat behind me if he saw a laptop on the floor. He did not. I felt my heart jump. That machine was my life. Had it fallen through some slot into the belly of the plane below? Had it gone all the way to the back of the plane and hit the bathroom? Was it damaged? Was some stranger now looking at where I had been on the internet?

I broke out in an awful sweat. As I looked around frantically, I saw a man five rows back smiling madly and waving at me. He held up my laptop. Yes! Everyone on the plane now knew I was an idiot, but at least I had my laptop back. I thought my ordeal was over, but as we leveled out after takeoff a flight attendant stopped at my row. Somehow she found out what I did! She read me the riot act for not following directions and for standing during takeoff. It was more than mildly embarrassing.

I broke the rules and I paid a price. The same goes for innovators.

I broke the rules and I paid a price. The same goes for innovators. The popular press loves innovators. Actually, they only love one type of innovator – the successful type. What they don’t show you is the innovator who fails, screws up, miscalculates, or otherwise comes up short. They don’t show you reality. In the real world, innovators find ways to break the rules in the name of making something awesome. Sometimes they win and more often than not, they lose. Whether you’re talking about a corporate executive or an entrepreneur, it’s the same – innovation requires risk taking and rule breaking. Sometimes you score, other times your laptop shows up five rows back.

The key of course, is learning – a fast as possible, as cheap as possible. If you don’t like taking risks, innovation is not your game. If you don’t like failing and having people look at you funny, innovation is not your game. If breaking rules and getting busted once in a while doesn’t sound like fun, innovation isn’t for you.

Innovation requires risk taking and rule breaking.

For the rest of you, here are my favorite tips for rule breakers:

Gain tacit approval.

If you know you can’t secure formal approval for something, go for super secret tacit approval. Some people say that it’s better to ask for forgiveness than for permission. Maybe, but you’ll definitely help yourself by entrusting at least one higher-level co-conspirator with your plan. Not only will they be able to give you needed advice, but if things don’t work as planned and the stuff hits the fan, they will be your advocate to minimize the fall out.

Codify what you learn.

Always engage a short post-hoc analysis of whatever it is you and team just tried – win or lose, but especially when you lose. Take good notes about the people involved and how they helped or hurt, the tactics used that did or did not work, etc. The next time you get the innovation itch, read that list and try not to make the same mistake twice.

Always engage a short post-hoc analysis of whatever it is you and team just tried – win or lose, but especially when you lose.

Associate with the most successful rule breakers you can find.

There is strength in numbers. You don’t look as crazy when you’re part of a gang. Associating with like-minded folks will give you a bigger sounding board, access to a larger network of possible collaborators, and, again, more people speaking positively on your behalf when one of your awesome schemes doesn’t pan out.

Apologize when needed.

If you don’t like to apologize when you’ve really stepped in it, innovation isn’t for you. Active change agents – even the best of them – sometimes inadvertently rub someone the wrong way. Hey, all is fair in love and war – and innovation. If you failed to keep someone in the loop, gained use of a resource that wasn’t yours, failed to support someone else’s initiative all in the name of helping your project – be prepared to step up privately and make amends. When you do – mean it! Otherwise you’ll allow trust to erode to the point that moving forward is difficult.

All is fair in love and war – and innovation.

Finally, try again!

You have to make this a habit. You don’t become skilled at rule breaking in the service of innovation if you’re only doing it once a year. Once a month is much better. Follow the advice above to help you survive, but stay after it.

It’s your choice. If you don’t want to be an innovator, that’s perfectly acceptable. If, however, you wish to chase the dream, keep your eyes open. Don’t believe the hype in the business press. Innovators are rule beakers and they fail as much or more than they succeed. If you go that route, use the advice above and maybe you’ll accomplish something awesome. Or maybe you’ll find yourself standing up during takeoff. Either way, it’s a fun path to follow.


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Image Credit

Dr. Dewett is an author, professional speaker, recovering management professor, and Harley Davidson nut. His job is to build better leaders and teams. He is the author of The Little Black Book of Leadership. His unique brand of energetic leadership knowledge has resulted in quotes in the New York Times, BusinessWeek, Forbes, CNN, Investors Business Daily, USA Today, and hundreds of other outlets. After beginning his career with Andersen Consulting and Ernst & Young, he has since spoken to and advised thousands of professionals around the world. Get to know Todd by visiting his home online at drdewett.com, his popular courses at Lynda.com, and his TEDx talk on YouTube.

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