The Six Attributes of Successful Business Mavericks

Let there be no doubt that the winners in business are those who break the rules and chart new, creative courses of action. I’ve seen it countless times as a CEO of major insurance companies and it’s good to know that rule-breaking is alive and well in business. Often, these trailblazers are running new, entrepreneurial businesses, but just as often they head some of the biggest names in business.


Think of Fred Smith, founder of FedEx, Steve Jobs, the guru of Apple, Inc., Bill Gates of Microsoft, or Richard Branson of the Virgin empire. Entrepreneurs like these are noted first and foremost for breaking the rules; for challenging the tradition which says, “You can’t do that.” Still, true maverick rule-breakers are too few on the American business scene.

If you want to join these successful business rule-breakers, you’ve got to start by thinking like they do. And the first sign of a rule-breaker is relentless curiosity. The man or woman who “cheats” on the old, outmoded rules of business is constantly asking questions and challenging the way things are done. Good cheaters take exception to established procedures and mores.

Rule-breakers often exhibit other attributes as well:

1. The willingness to adopt new perspectives whenever possible
2. The openness to try new things and to do old things differently
3. The compelling drive to act on ideas to test their true value
4. The eagerness to listen to others and profit from their input, regardless of who gets credit
5. Respect for and support of others when they propose new courses of action

Rule-breaking behavior requires an openness and willingness to look at the world in new ways. Rule-breakers know that new ideas need nurturing and support. But they know that thinking about a new idea is not enough. The true value of a good idea resides in its implementation. As management expert Peter Drucker said, “Ideas are cheap and abundant. What is of value is the effective placement of these ideas into situations that develop into action.”

On the surface, rule-breaking doesn’t require any special skills. You don’t have to have an MBA from an Ivy League university. In fact, you don’t need a degree at all. But if it’s so easy to be a cheater, and the potential for reward is so great, why, then, doesn’t everybody do it?

The Will to Cheat Is Hammered Out of Us

When we’re young, we’re much more apt to be cheaters. Children commonly exhibit the cheater’s inclination to question why things are done the way they are. It’s natural. As soon as babies can talk, they ask, “Why?” It’s often irritating for parents because they don’t always have the answers. So the response is “Because.” Or, if the kid persists, “That’s the way it is. Go watch TV.”

Schools only exacerbate the problem. The educational system is founded upon the pedagogy of answering questions, not asking them. Students are rewarded for the proper rote playback of answers, not their ability to question the reasons for the answers or, sometimes more important, the assumptions behind the questions. The pressure to “go along with the crowd” is overwhelming for anyone, particularly kids in their formative years. Not surprisingly, most buckle under the pressure. A child is forced to see things the way their peer group does, dress as they do, talk as they do, and worse, think and act as they do. Pretty soon, a child’s willingness to question and break rules is exorcised as if it were a troublesome evil spirit.

Rule-Breakers on the Fringes

We have to recognize that daring to think and do things differently exposes us to risks as well as rewards. But you know what? Even though you may risk the ridicule and tsk-tsk of your friends, teachers, parents, business associates, boss, and an endless string of others; even though there is a risk that you’ll come up with a dumb idea for which you’ll be chastised; even though some may perceive you as a show-off or know-it-all; even though all of this may be true, when you finally succeed by doing things differently, the reward and personal satisfaction is so much better than the punishment, it’s not even a contest.

The only reason the downside exposure exists is simply to control you: to intimidate you so that you’ll be unwilling to be a rule-breaker and a creative thinker. The result? Many potential rule-breakers are afraid to engage in behavior that could potentially make waves. Instead, they lay low and avoid the possibility of future embarrassment and pain. The bottom line is that, even though we start out in life as rule-breakers and cheaters, most of us become timid feeders in a sea of conformity before we ever get our first job out of college.

Fortunately, even if one is not a born cheater, cheating can be an acquired talent, a talent well worth learning and practicing. To develop and nurture this talent for ourselves, we have to overcome the way our psyche has been bullied for so long in an effort to get us to stop asking questions. To achieve real success in our life and career, it is essential to recondition ourselves to challenge convention. I know that this is easy for me to say. I’ve made my millions, and I have little to lose now by rocking the boat. But I insist that you can do it too.

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