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I mean, Paul McCartney must wake up every morning and think: ‘How the hell did all this happen?’,” says Paul Oberschneider. “He probably wonders whether he’s a Beatle or whether he’s just a guy called Paul.” It’s talk of impostor syndrome that’s prompted Oberschneider’s musings on the internal misgivings of Paul McCartney. He’s qualified to speak on it, too: Oberschneider - a fellow ‘guy called Paul’ - has a laundry list of entrepreneurial successes. He founded two astronomically successful real estate businesses and invested in London healthy fast food chain Vital Ingredient before selling his stake last year. By every measure, he’s a success. But when asked whether he still struggles with impostor syndrome, he answers without hesitation: every day. “I think there was a point where I felt it less - but I certainly did experience impostor syndrome in the beginning of my career and I do now.
“It also changes form. Before it was ‘why me?’ Now it’s more like ‘Was that just luck? Did that really happen? Could you do that again?’” Oberschneider isn’t the only successful person to acknowledge these feelings openly. Even Maya Angelou - that is, Nobel Laureate Maya Angelou - once said: “I have written eleven books, but each time I think, ‘uh oh, they’re going to find out now. I’ve run a game on everybody, and they’re going to find me out.’” At its essence, impostor syndrome is exactly as Angelou described it: a fear of being found out, a disbelief that you earned the station you’ve risen to. The problem is, as the American educator and writer Freddie DeBoer put it recently: “Success becomes hard to enjoy because it is filtered through this frame of being counterfeit or a mistake.” For many entrepreneurs, success can feel like a sword of Damocles. At any moment, your hard work can be discredited. “I think with our first round of investment we felt like fraudsters,” says Stormburst Studios co-founder and CEO Derry Holt. “Why on earth someone was giving us £150,000 was beyond us, and why they wanted to give us even more in a few months time felt ludicrous. We were terrified (still am) of burning their cash and being called liars or frauds.” Alex Price, the founder of the agency 93Digital, can also recall a specific moment when impostor syndrome hit the hardest: “The first time we won a six-figure project,” he says. “It took three or four months to deliver. There was definitely a point where I thought ‘my god, is this worth it and can I get this across the line?’
“For me, impostor syndrome comes with growth. It’s almost in some respects, the founder doesn’t keep up with the thing they’re running. A lot of founders can experience crazy growth. It has impacts on how they perceive themselves.” This sounds altogether hopeless, though. Even success - as in Oberschneider’s case - can’t insulate the entrepreneur from feelings of inadequacy. But speak to founders long enough and the idea that emerges is altogether more subtle. The subconscious feelings of imposterdom mightn’t go away - but they also don’t stop people from being successful. “Every single day feels like a learning experience and one I don’t feel qualified to do,” says Holt. “But in the same step, ‘he who dares wins’ - get comfortable being uncomfortable because even the big boys sometimes doubt themselves.” In his book The Last Messiah, the Norwegian philosopher Peter Wessel Zapffe prescribed what he called “remedies against panic”; ways for humans to combat the low flying anxieties of existing. One of Zapffe’s remedies was sublimation: the refocusing of energy away from negative outlets, toward positive ones. Without realising it, Oberschneider, a considerably more cheerful fellow, channels Zapffe: “One day you wake up and you say ‘fuck it, I don’t care and this just what I’m doing right now’ - it’s much more manageable. “You say - and this only comes with age - ‘I don’t give a shit’. I don’t care what anyone says. If you care about what your peers think it's easy to fall into that trap.” The truth is, according to these entrepreneurs at least, is that the impostor syndrome doesn’t go away - you just get better at distracting yourself.