Imposterism Afflicts Many Entrepreneurs

Published in the San Diego Union-Tribune, March 21, 2016

The great imposters know no self-doubt.

Victor Lustig sold the Eiffel Tower in 1925 for $30,000 (the buyer was so embarrassed that he never asked for his money back) and later, Lustig convinced Al Capone to invest $40,000 in a fraudulent stock deal. However, all good things must come to an end and he finished his days in Alcatraz.

But does your company need an imposter? And if so, what kind?

Many entrepreneurs are afflicted with the “did I deserve it” disease. Professor James Heskett, Harvard Business School, has written a paper on the “imposter phenomenon.” And of course, one of the findings is that people who experience this feeling the most are exactly people who have truly achieved something – “who are demonstrably anything but frauds.” But no matter the number of honors or awards, they are suspicious of their right to have them.

I am chairman of a company poised on the brink of success. The chief executive was ruminating and muddling about on all the things that could go wrong, even though at that moment, revenue and acceptance was on the horizon and it appeared the stars were aligned. In a quiet moment, I asked him: “Do you feel you deserve success and wealth?”

And to my surprise, he hesitated, and then he mumbled “Finally, sort of, yeah, I guess, kind of, sure.”

I can tell you, this dude is a rock star on the brain scale. The neutron bomb word was “deserve.” I mean, I have been in therapy for over 30 years, and we haven’t yet gotten around to working on that word.

I would suggest that the imposter syndrome is also the single most compelling force in personal achievement. What is it in our pasts, in our parenting, in our histories that haunt the entrepreneur? It is often the most brilliant who worry, “What if they find out that I know nothing?” A pretender to the throne.

I am a major investor in another company where the CEO is a tormented soul and doubts his ability, but is genuinely brilliant and hugely competent. This fascinates me. The trait is a double-edged sword. If not managed, it can overwhelm someone and lead to not just fear of failure, but also actual failure.

On the other hand, it is a very powerful force in achievement. These individuals set high standards and then excel beyond them. Their self-worth button, when pushed, does not defeat them, but rather elevates their effort and their performance.

I love the contemplative imposter because he is deeply aware of the vagaries of the business, of the nuances of the deal, of the single moments that challenge him constantly, and his feeling that if he falls off the high wire, he risks exposing himself to others as a fraud. But it is this exact tension that also brings out the very best in the entrepreneur. Not content to rest on his laurels – earned in truth, but dismissed by himself – he will battle valiantly to keep from being “exposed.”

But self-doubt, while powerful as a force for achievement, pales in comparison to forces over which the entrepreneur has no control. A recent study asked venture capitalists to identify the main reason for their massively successful exits for their companies. They did not say, market or team or technology – 62 percent of them said “timing.” Think about that: These titans of genius, these monsters of the midway of investing and venture, conceded that over half the time, they just happened to pull an ace on the river. Wow, the luck of the draw. That is a scary way to make a living, whether VC or entrepreneur.

Can your company find a safe place for the highly talented imposter to excel?

Rule No. 459

The emperor has clothes, but they are hanging in the closet.


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