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How entrepreneurs can conquer their secret insecurities

Popular culture pictures entrepreneurs as brash go-getters. But in private, many are plagued by self-doubt

Writer and actor Mindy Kaling talking on stage

Writer and actor Mindy Kaling on the value of entitlement: “Work hard, know your shit, and then feel entitled.” (Thos Robinson/Getty)

Warren Buffett doesn’t seem to be especially afflicted by feelings of inadequacy. “I always knew I was going to be rich,” the billionaire CEO has famously said. “I don’t think I ever doubted it for a minute.”

It’s impossible to know whether the Oracle of Omaha is really so sure of himself, but if he is, he’s a rare specimen. While stereotypes abound about entrepreneurs overflowing with confidence and conviction, self-doubt is a lot more common in the profession than most people realize. Research shows that as much as 70% of the general population has experienced what psychologists call imposter syndrome: the suspicion that your success is somehow undeserved and that you will eventually be exposed as a fluke or a fraud. The feeling of inadequacy is especially common among gifted, high-achieving people with something to prove—the exact type of person who tends to be drawn to entre­preneurship.

Consider a few high-profile examples: Shark Tank star and real estate titan Barbara Corcoran has said she’s plagued by a nagging voice in her head telling her she’s stupid. New-media mogul Peter Shankman (whose CV includes founding the popular website Help a Reporter Out, among other things) has called self-doubt his biggest obstacle. Kelsey Ramsden, twice named Canada’s Top Female Entrepreneur, has admitted to telling herself “you are not meant to be here” while hiding in a washroom before a major speaking engagement. Even Steve Jobs, the poster child for fearless empire-building, reportedly felt insecure about his achievements much of the time.

If über-entrepreneurs like these are beset by self-doubt, one could make the case that it may not be such a bad thing; perhaps insecurity—specifically, having something to prove—can provide the necessary fuel for pushing themselves toward success.

That does happen sometimes, and it makes for the kind of underdog stories that top bestseller lists and weekend box offices. But the far more common reality is that confidence opens doors that uncertainty does not. Studies have shown that entrepreneurs with high levels of self-assuredness are better at handling stress, managing risk, delegating and, perhaps surprisingly, seeking out new knowledge. Self-assured bosses are also proven to attract better employees and sell more stuff. These are all desirable outcomes, and they are tough to achieve when you’re second-guessing every action.

Of course, contrary to the teachings of countless self-help books and “fake it ’til you make it” advocates, confidence isn’t something you can turn on with a switch. It requires a fundamental change in the way you see yourself and that is not a superficial undertaking.

There’s a solution I like, and it comes courtesy of Hollywood—specifically, from actress-writer-producer Mindy Kaling, whose impressive success as a young woman of colour in a town run by old white men routinely spurs people to ask where she gets her confidence. Setting aside the fact that it’s kind of an insulting question, she gets asked it so often that she devoted a chapter to the subject in her new book, Why Not Me?, in which she distils her formula to this: “Work hard, know your shit, show your shit, and then feel entitled.”

To most people, entitlement is an objectionable trait, but in Kaling’s view, it gets a bad rap. “Entitlement is simply the belief that you deserve something. Which is great,” she writes. “The hard part is, you’d better make sure you deserve it.” And you can do that, not with hubris or brash posturing, she continues, but by logging the hours and doing the work.

Framed this way, confidence is eminently achievable, especially since there aren’t many good entrepreneurs out there who are unacquainted with hard work. If you know your business inside and out, have a clear plan for its growth, and maintain solid expectations that it will succeed (which are based on more than just wishful thinking), there’s no reason you shouldn’t carry yourself with a bit of the ol’ Buffett swagger. And if you don’t have those things, well, maybe it’s time to take an honest look at what you’re doing.


Shark Tank star Barbara Corcoran on battling insecurity: