09/07/2013 18:50 BST | Updated 07/09/2013 06:12 BST

The Day I Told Amy Winehouse She Was a Risk I Wasn't Willing to Take

Sometimes failure takes you to more interesting places than success. Because you're deprived of success, failure teaches you what the true components of attaining success are. Hard work , tenacity, desire, ambition and brains. They're all important factors but not the most important.

What failure really teaches you is that success is, more than anything, down to luck. And the best way of finding that luck is to take risks.

I'm more convinced than ever that risk is essential to creative industries. We don't work in an environment of certainty or indeed logic. If we don't take risks, if we don't risk failure, we won't fulfil potentials. We might 'get by' by playing safe but we won't succeed.

That's one of the defining characteristics of our digital age and its inexorable gallop into the unknown. 'It's a risk, who knows if it'll work, sod it let's do it anyway.' The great irony, however, is that the creative industries have handed the reins to geeks and financiers. They're the 21st century risk-takers.

Many years ago I worked for an editor who demanded that everything be done a certain way, every idea needed to conform to the newsroom sausage factory. And the editor thought it worked because it meant the paper had a solid identity, it didn't risk alienating readers. The unexpected was excised.

And one day a music critic freelancer, Gary, asked me to take a risk on a neighbour of his. Gary came to me because of my North London Jewish background, similar to the amateur singer he wanted to help turn into a star.

They came into the office and after a coffee and chat I politely took the girl's lovingly-constructed CD back to my desk and threw it in the bin. This mumbling 19-year-old girl was overweight, with bushy black hair that hung over her morose chubby face like a curtain, she was shy to the point of boring, wore what looked like men's clothes and, worst of all, sang jazz. 'Sorry love it's just not going to happen,' I wanted to say in my best Simon Cowell voice. No one's going to take a risk on you.

I'm reminded of that incident as I sit in my office listening to my daughter playing Amy Winehouse's albums over and over again, and I daren't admit to her that I dismissively chucked Amy's homemade, personally annotated CD in the bin that afternoon because I didn't have the energy or nerve to take a risk. I had been conditioned to perform my role in a certain way - the creativity, danger, excitement had been removed. And I was a lesser journalist for it. I was also a complete and utter fool.

Now, having taken the biggest and possibly most foolish risk of all - reinventing myself by launching a new career - I appreciate that success isn't just measured by titles, numbers of underlings, constant Blackberry pings, occasional pats on the back and a generous expense account, it's measured by how alive we feel. And, working in a creative industry, you only really get that feeling when you're either taking a risk or watching that risk pay off.

Corporates would do well to remember that part of the reason they lavish enormous amounts on nebulous disciplines likes PR, advertising, marketing and (most importantly) content is that they're paying for risk, for lateral thinking, for trying to see things in a different way.

Some ideas might not work, some approaches might not even get off the ground but unless we are prepared to fail - or not scared to fail - we won't find that crucial bit of luck that puffs out our chests so we cross the finishing line first.

It pays to be different. It pays to construct teams with entirely different backgrounds, disciplines and points of view. If we all sang from the same songbook what a dull place we'd live in. Amy could have told you that.