The One Key Trait for Successful Entrepreneurs: A Tolerance for Ambiguity

Let’s face it. When you look back on your life, you normally tell the story in a way that makes you look good. The same is true with entrepreneurs. After a business success, we often carefully choose and arrange the facts so that we are the hero of the tale. (If you doubt this is true, just ask me about any of my business successes.)

Usually, the story goes something like this: “I came up with an incredible vision. Assembled the right team. And through brilliant decision making and the sheer force of will, created something out of nothing.”

It’s a nice story line. It makes the entrepreneur the driving force of the tale. And it’s true, or at least a version of the truth.

But this isn’t what entrepreneurship feels like in the trenches. There’s no clear story line. Happy endings are far from certain. There’s a sense of chaos, hectic decision making and moments of great fear and doubt. You are making up the story as you go.

Life is difficult. So why should business be any different? An entrepreneur’s journey is a hero’s journey, but it’s a much more difficult and tortured journey than most of us would like to believe.

And it’s a tolerance for ambiguity that makes all the difference.

What is a Tolerance for Ambiguity?

Entrepreneurs need vision. If you want to become a successful entrepreneur, you need to be able to say: “See that hill? That’s an important hill. We need to take that hill!” And you need to say it with enough conviction that people will join with you. But if you have the instincts of an entrepreneur, what you’ll do next is surprising. As soon as your merry band sets off toward the hill, you’ll say to yourself: “That’s probably not the right hill. I bet I’m wrong. I need to be looking for clues that we need to change course.”

Sounds a little schizophrenic doesn’t it? Even a little disingenuous. But to a natural entrepreneur in the heat of battle, it makes perfect sense. Because what he or she really means is: “I think that’s the right hill, or at least it’s probably the right direction.”

The ability to hold both these ideas in tension, to commit to charging ahead while looking for evidence to prove you are wrong, shows a high “tolerance for ambiguity.”

It’s an entrepreneur’s willingness to paint a compelling vision and charge ahead that creates order out of chaos one step at a time. It’s a willingness to be open to new information and make mid-course corrections that mitigates risk. The ability to do both of these at once, in the face of great uncertainty, is a tolerance for ambiguity that sets an entrepreneur apart from the rest of the world.

Can a Tolerance For Ambiguity Be Learned? Absolutely. But, sadly, our assembly-line K-12 schools, as well as most business schools, teach all the wrong lessons.

The best way to develop a tolerance for ambiguity is to make mistakes early, cheaply, and often. To learn that failure is a blessing, if it helps you grow. To learn that failure in pursuit of a worthy goal is noble and that questions are more important than answers.

That’s why at the Acton School of Business and the Acton Academy, we work so hard to give our students a chance to practice failing, both in the classroom and in the real world. That’s why we encourage them to begin with the end in mind and to believe they can change the world. And why we work hard to instill the habits of trial and error experimentation and self-reflection.

In essence, we believe that “learning to know,” or book learning, is important but only if it helps you “learn to do” and “learn to be.” Life is a matter of becoming who you were meant to be by using your gifts to do something that matters to you and others. That’s the real hero’s journey of a principled entrepreneur.

Is the life of a principled entrepreneur for you? The answer to this question may come down to your courage and willingness to learn through trial and error—your ability to tolerate ambiguity. Resolve now to seek out small challenges towards a greater vision and to steel yourself to welcome the small failures that make you stronger. Begin to increase your personal tolerance for ambiguity, and you’ll be well on your way to strengthening that rarest of all entrepreneurial traits.


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