6 Reasons I Share Stories About My Failures

It's fundamental to connection and leadership

Photo by JAIME CUADRA on Unsplash

“What’s the number one thing holding you back from success?”

The seminar leader asked this question just minutes into the Zoom call and invited anyone to raise their hand and respond. There were hundreds of us—entrepreneurs seeking inspiration and guidance to grow our online business.

Inside my head, the answer was immediate.

Fear of speaking up.

Ironically—I then hesitated to raise my electronic hand.

As a professional speaker, I’m no different than anyone else in a new situation with unfamiliar faces. The mechanics of human participation revolve around psychological safety. So I wanted to take the temperature of the space before exposing myself to possible rejection or ridicule.

But there are moments when we need to be able to bypass the automatic caution we apply to new situations and take a leap.

This was one of those moments.

It’s only been months since I decided to help others with the skill of storytelling and speaking. And I’ve been getting traction quickly, because this is a common human problem—that we’re often hesitant to speak, or share our story.

Here I was in front of a few hundred entrepreneurs, all of whom are candidates for the coaching I have to offer. Had I raised my hand right away and shared my fear of speaking up — as a speaking coach! — that would have served everyone tremendously.

The message would have been:

If someone who is a professional speaker experiences anxiety around speaking, maybe I’m not a hopeless case.

It’s one of the most disabling myths in our world—that feeling afraid to speak is an indication that something is wrong.

It’s one of the most disabling myths that exists in our world—that feeling afraid to speak is an indication that something is wrong.

Very often, hesitating to speak up is a sign we have something valuable to say. And I had missed my opportunity.

But it got worse.

As I sat there observing the clenched knot in my gut, telling myself I needed a minute to gather my courage—and then I’d raise my hand—somebody else jumped in and said essentially the same thing.

“I’m afraid to put myself out there.”

Has this ever happened to you? You had a brilliant share or comment, but then someone else beat you to it, because you hesitated?

The seminar leader’s face lit up over his comment.

“Yes!” she said. “This is a common stumbling block and I appreciate your courage to speak up.”

She then went on to engage this person, a 19-year-old kid, about his new business to build and promote a course on TikTok about how to hike barefoot. In the span of a few minutes she had everyone in that session looking at his profile and quadrupled his existing number of followers.

But what a delicious lesson.

I find the universe to be constantly delivering humor, irony, and surprise to my doorstep—exposing my foibles and self-adopted fetters—giving me the chance to self-reflect and grow.

So there I was. The silent, experienced professional speaker watching wisdom flow from the mouth of innocent bravery.

Anyone, at any time, can align with the laws of courage, innocence, vulnerability, and authentic expression to make good things happen for themselves and others in the world.

But this time, it wasn’t me.

6 reasons I share failure stories

I have plenty of stories about times I’ve shown up in the moment with courage.
Those are cherished and welcome moments for me when they occur.

But my favorite stories feature an example of someone else who has been inspiring, and feature me missing the mark.

Why?

Because I benefit in multiple ways from sharing such stories.

1. Part of me is an insecure child desperate for praise. That part of me would share his success stories all day long. I need to keep an eye on the stingy part of my character that wants all the attention for himself. The best way to do that is to praise others.

2. My insecurity causes me to avoid opportunities to succeed because I’m afraid of looking foolish. But when I deny that my insecurity exists, I only help it to keep blindsiding me in moments that count. Telling stories about my fears helps me to keep them visible, maintain a sense of humor about them, and navigate them with more self-awareness.

3. By default, I tend to focus on my own merits, strengths, and talents far more than those of others. There’s an entire world of extraordinary humans out there. I want to practice seeing, elevating, and celebrating them so I can both learn from and be inspired by them.

4. Owning the parts of me that are unflattering and unattractive helps me to connect with my audience far better than holding up only the good parts I want others to notice. We’re culturally trained to disown our shadow, but when we hide pieces of ourselves, we never feel fully seen. Authenticity affords our deepest connection with others. My willingness to go first by showing my flaws creates an atmosphere for authentic exchange.

5. When I’m willing to own and describe, in detail, the modus operandi of the small and fearful energies that are trying to remain in charge of my life, I’m giving myself a tour behind enemy lines and gaining knowledge of its defenses. This makes me more aware and alert to its methods of control. Eventually, after repeatedly sharing stories of my failures, I stop falling prey to their mechanics.

6. Finally, the more I do this, the more I create a network and community of friends, colleagues, and influencers who are willing to share similar stories. I meet more people who have the intention to be similarly self-honest. I’m admitted into their confidence, I’m invited into inner circles, and more people avail themselves to me as friends.

Embracing failure is a cornerstone of leadership

“The greatest crime is the overlooking of who you really are in favor of the story of who you think you are.” ~ Wu Hsin

A research study called the Aristotle Project was conducted recently at Google to explore the dynamics of effective teams.

The results cited psychological safety as the most important component of team success, identified as establishing “[the belief] that no one will make fun of or punish you for admitting your mistakes, asking questions, and presenting new ideas.”

We can only imagine that stories told by leaders that demonstrate a tolerance for failure, and even an appreciation of it, will help foster such a team environment.

As the French dramatist and reformer Voltaire put it many centuries ago, “The danger which is least expected soonest comes to us." 

In many cases, the behavior that we perpetuate in our blindspots is the danger that we least expect. In that context, celebrating our failure stories may provide the surest footing we can find, as individuals or as leaders of a team.

“Every great leader is a great storyteller.” Howard Gardner, Harvard psychologist.

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