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How Good Stories Come From Bad Judgment (on Linkedin)

Nasrudin is known as much for his wisdom as his foolishness, and many are those who have sought out his teaching.

One devotee tracked him down for many years before finding him in the marketplace sitting atop a pile of banana peels–no one knows why.

“Oh great sage, Nasrudin,” said the eager student. “I must ask you a very important question, the answer to which we all seek: What is the secret to attaining happiness?”

Nasrudin thought for a time, then responded. “The secret of happiness is good judgment.”

“Ah,” said the student. “But how do we attain good judgment?”

“From experience,” answered Nasrudin.

“Yes,” said the student. “But how do we attain experience?”

“Bad judgment.”

                                                              – Joel ben Izzy, The Beggar King and the Secret of Happiness

Bad judgment. As much as we’d like to believe otherwise, our greatest leadership stories are formed from our biggest screw-ups. We try, we struggle, we fail. We learn something and we try again. These struggles often become our best allies in achieving our goals later in life. But they may also be hard to communicate, as people might look up and think, “Easy for you to say, you’re the woman standing at the podium…you’re the founder…you’re the honcho. Easy for you to say.”

And it might be easy to say. But hard to make it relate. So, if you’ve looked out at your listeners and felt your findings, your pitch or your message was bouncing off them like hail hitting the hood of an old Buick, here are some suggestions of where to look.

Your challenge, should you choose to accept it, is to develop ten powerful stories that you can tell, to different audiences, in different ways. You may want to start with three, but I believe if you’ve been walking this earth long enough to be able to read these words, you will eventually come to see ten powerful stories that deliver your critical messages, your key insights, your wisdom from your life, and the essence of your work. These might be origin stories, that tell where you come from, impact stories that reveal the work of your organization, or vision stories, ones that show us where you’re going – and maybe even where we’re going ourselves.

I used to believe that when it comes to telling stories, you’ve either ‘got it’ or you don’t. But after many years of working with clients facing all kinds of hurdles with their storytelling, and after years of trial and great error in developing my own story practice, I believe that everyone can tell good stories. It’s just a matter of diving in. The practice of finding them is to go through and look at your life, and then gather them and see how they map to your critical messages.

My hope is that the tips below will help you strengthen the stories you have, help you unearth the gems you know are there but seem as yet untellable.


1. Your Current Go-Tos: These are stories you already tell, but that could use some shaping.

They may be stories you might tell at dinner parties, at key management moments, at keynotes, or to your kids.

Ask yourself a few questions about the stories you already tell. What’s working in these stories? Do they drop into the suspense and the surprise, and land a key insight? Do they tell it all at the beginning, leaving the end flat – or just wander on with no certain point? What does the story carry that compels you to tell it?

One might be one that tells where you come from or how you found your passion or your career. One or two might be an a-ha moment. Or one might be a simple story of a mistake and a lesson learned. One may be your core story, the story that holds all of your stories, telling where you come from, what you do and where you’re going. But most likely all of them are stories which include lessons you’ve learned about how the world works. And if your experience happens to have been happen to have been preceded by a bit of your bad judgment, so be it.

2. Your Reserves: Stories you may have known but don’t tell, and need shaping.

Maybe it’s a story that you heard from someone else that could use some shaping, or one that you told once that fell flat. Maybe it’s something surprising that happened once – something that just won’t let you go – but doesn’t seem like a story yet at all. These are the parts and pieces may not quite be ready to tell, but have promise. They may even be stories you’ve written, but never told, or ones you’ve heard or read and would like to tell but haven’t found the right time and place.

I suggest that as you begin working on your reserve stories, that you reach out and find a story buddy. A story buddy (your friend, co-worker or partner) is someone that first and foremost provides a safe territory for you to experiment. Someone that’s willing to hear a story that is totally not yet ready to tell – after all, the difference between one not ready and one that’s a go-to is in the telling! You may just need a tweak or two once you tell it, and you can ask your story buddy first to listen, and then to give you some feedback.

Looking at your reserves, you will likely discover stories of indecision, deep questioning, risk or, yes, even bad judgment. Because if you truly want to endow your audience with a good lesson and good direction, there’s no better way that to let them learn from your own experience. But you can’t just tell them the trial – or only what you’ve found. You’ve got to shape those stories into a journey. So rewind before that story a bit, and see how the world was.

Then walk through the act of learning the lesson, and tell us how the world was different on the other side.

3. Your Sparks: Insights, lessons and key moments in your life that haven’t yet become stories.

This is the most fun territory, because the discovery of raw material can be so surprising. These are more like moments, key changes that have happened in your life or lives around you that you may have never known how to effectively share. Or perhaps they just play a background role in the long list of things you rattle off when you share your life’s journey.

To bring these sparks to life, go back into an experience and freeze them in time. Treat your story like a wax museum, and bring your curiosity to see what else is there. Can you smell the green grass on the field? Can you feel the soft rain on the corrugated metal roof, when there’s a knock at the door? Was the take-away what you once thought? You may even find that there are other lessons waiting for you.

So as you scan your life, mark the key moments, the lessons, the upturns and the downturns. Life has its way of normalizing things, of making the extraordinary seem ordinary. But in truth, our lives are lined with great discoveries of learning. To find and tell your stories is to rediscover that magic, every day. And sometimes that means discovering a lot of bad judgment that has been the foundation of your greatest lessons.

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