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John Cleese was on The Late Show with Stephen Colbert recently, talking about how Monty Python sold their first series. Cleese, Chapman, Idle, Jones, Gilliam and Palin had only met once, but they decided to pitch a show to the BBC.

What’s astonishing isn’t how young they were (very), or that they hadn’t discussed what kind of show it should be before the big meeting.

No, what blew my mind was the man from the Beeb saying “OK,” and trusting that they’d bring back something great. Because frankly, you’ve got more chance of finding a unicorn in your bathtub than a television executive who says “Yes.”

Contrast that with a meeting I had years ago. The Creative Director called writers and art directors into the board room under the guise of a “status meeting.” He closed the door, looked at the dozen or so teams and said, “If you don’t win awards, you will be fired.”

He said a bunch of other things after that, but no one was listening. We were too busy calculating how much was left in our chequing accounts.

Within weeks, half the department had quit. Not because we couldn’t win awards, but because we didn’t feel motivated – or relaxed or playful, two things essential to being creative – by having a gun to our heads.

When failure is not an option, fear takes over. And fear is creative kryptonite.

“The process of developing television shows is really, can be really demoralising. And I always liken it to – and it’s the same, I guess, for actors – it’s as if there was a restaurant that opened in your neighbourhood, and you got all this positive feedback. You read good reviews, had good word of mouth, you’d drive by and it was busy and it seemed like, ‘Oh, this place looks like it’s great. Let’s go ahead and try it out.’ And then you get a table at the restaurant, and instantly go back to the kitchen and tell the chef how to cook things. That’s what casting and buying shows is. It’s like:

‘This guy’s talented, look at all this work that he’s done! Let’s hire him.’

‘Yeah, let’s!’

‘He wants more money.’

‘Give him a little more money.’

‘OK, we got him!’

‘He’s ours? Now let’s treat him like he’s an idiot.’”

– Andy Richter, from A.D.D. Comedy with Dave Razowsky

Business fears creative because there are no guarantees. It wants to control things; after all, there’s usually a lot of money at stake, whether you’re making an ad, a film, or Kanye’s next collection. But art can’t exist without the possibility of failure. And as my first boss told me, the greatest risk is in playing safe.

I think that’s why so many successful actors still improvise. It’s a chance to take risks, to do something a little crazy, knowing they have the freedom to succeed or fail spectacularly.

The opposite of fear is trust. That’s scary, because you have to make yourself vulnerable in order to trust someone. But as Python demonstrated, the pay-off is so, so worth it.

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