doubtLast week I wrote a post about the pressure of keeping up appearances. The feedback and comments I received, from both friends and strangers, told me I had touched on something close to home. Many of the entrepreneurs I spoke to also described their struggles with self doubt. People told me they felt like frauds for not being able to erase their uncertainty, and it occurred to me that there is a general belief that the key to being successful requires overcoming all traces of doubt.

But this belief isn’t true. It’s a myth foisted upon us by motivational speakers who spin entrepreneurship as a simple matter of feel-good self esteem in order to sell their wares.

The truth is most entrepreneurs never overcome their doubt. In fact, the day you overcome all doubt is likely the day you become blinded by your delusions of control and perhaps even greatness. What entrepreneurs really learn to do is live with doubt. And learning to live with doubt, being able to accept doubt, is a much more powerful thing because it allows you to continue questioning assumptions while still moving forward in the face of uncertainty.

One of the negative side effects of the “crush it” culture that I’ve criticized in the past is that it typically comes with a strong dose of false confidence. People who subscribe to it will tell you that you’re supposed to wake up every morning like some kind of force of nature ready to tackle the world. I find these are often the weakest people. They project bravado as a disguise, and when the world comes back swinging, as it almost always does, they are usually the first ones to cave, when their thinly veiled self confidence is hit with the reality that whatever they’re doing might not work. They end up with a cognitive dissonance in their head that can only be reconciled by making up false excuses or embracing a delusional self image of success that isn’t supported by reality.

On the other hand, those who have learned to live with doubt are certain only that the future will come. What that future looks like is malleable. And it is this ability to deal with doubt that not only empowers an entrepreneur to experiment, but allows them to adapt to changing circumstances.

As an entrepreneur, it’s logical for you to have a measure of self doubt. You don’t know where you’re going or what the future holds. You’ve chosen to sail into uncharted waters. But even in the face of uncertainty, you’re still sailing forward while the vast majority of people who seem so sure of themselves are back on dry land. And rest assured, anyone sailing into the great unknown while claiming supreme confidence is either delusional or lying.

Many people think that having doubt makes you weak. On the contrary, it is the ability to live with doubt that makes you strong. Those who need the security of a predictable future, or can’t let go of the inflexible self image of who they are or what they are supposed to be, are doomed to be trapped by the certainty that they seek.

These are the people you see climbing corporate ladders, or sitting at conferences looking for reassurances and magic pills from the speakers on stage. These are the people you see laying claim to the word “entrepreneur,” but who always have an excuse for why they can’t quit their day job and make the leap. Worst of all, these are the people who have fooled themselves into believing that they have all the answers and proclaim it so loudly that others blindly follow them.

Consider what Bruce Lee said about “second-hand artists” who blindly follow or accept another’s pattern: “As a result, his action is and, more importantly, his thinking become mechanical. His responses become automatic, according to set patterns, making him narrow and limited.” This is the fate of those who require the certainty of clear answers and set rules. This is the fate of those who are unwilling or unable to live with doubt.

[Illustration by Hallie Bateman]