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The Freedom to Fail


By Kelly Leonard – Executive Director, Insights and Applied Improvisation

I was reminded the other day that I could write a thousand posts about a thousand so-called victories and it wouldn’t amount to a fraction of the failures that I have experienced in my career.

I failed colleagues; I failed the audience; I failed myself.

Sometimes it was shows that didn’t sell and sometimes it was creative work that was decidedly sub-par. The more painful failures are the one’s where I let down the people I cared about most. It is safe to say that we all have a list of failures, but it’s incredibly important – I’ve learned – to truly own your own failures.


Because this failure thing? It never ends. And you’re way better off finding ways to weave your failures into your personal narrative rather than attempting to hide them or, worse yet, act as those failures were the fault of someone else.

Do you have kids? I do. I can think of no greater gift than to give them the gift of resiliency in the face of failure.

The writer Douglas Coupland has a great line: “Sometimes the best lighting of all is a power failure.”

This is perhaps the healthiest aspect of improvisational practice: it allows you to model failures over and over again, building up your ability to repeatedly make mistakes and then… to persevere. For most people, the “power failure” will serve to jolt them out of their complacency and provide them with a whole new set of fresh insights. For those who practice improvisation, you don’t have to rely on the major screw up to adapt your thinking. We are taught that mistakes are gifts and we use them as part of the story we are telling – a story, by the way, that is not just being told by us. While not quite a rashomon, any personal narrative that exists in the world is part of our own making, part the experiences and interactions we’ve had with others and the lens by which the professional prognosticators view our story. In the case of working in the entertainment businesses, that third party is the critic; in the case of a business person, it could be a trade publication, association or any other professional body that looks to name the winners and the losers in a particular field of expertise.

While we all love winning, we have to learn to use losing.

The failures, the mistakes, the losses – they are all part of cartography for the map we’re making every day.

Once businesses and individuals understand the need to destigmatize failure, the sooner that they can get to the more important business of adding the knowledge of a mistake to their own toolkit.

learning and development,  Navigate an Uncertain World in No Uncertain Terms,  talent development,  We can't innovate


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