One of my most embarrassing moments involves a speaking engagement, a skirt, and a very windy day in Texas.
I had been invited to speak in front of about fifty people. I parked my car in the parking lot outside the venue and took a moment to collect myself. I don’t usually get nervous when I speak, but I do get a little excitable, so I like to take a few deep breaths and say a quick prayer before heading in to greet people.
So after I turned off the ignition, I breathed deeply, silenced my phone, and smoothed the full skirt of my dress. I was ready.
I stepped out of my car. And a gust of wind lifted my skirt up so that the hem slapped me in the back of the head.
I shrieked. I fumbled to pull it down. I pushed the hair out of my face, and looked around.
Please, please, please, let the parking lot be empty, I thought.
Then I spotted them: a man and a woman sitting in their car directly behind me and, now, courteously pretending not to notice me.
I had just mooned two members of my audience.
That, my friend, is not the amazing thing. This is:
Standing there in the parking lot, I laughed at myself. At the situation. At how silly I must have looked spinning in a circle, scrambling for my skirt, my long hair flailing in the wind. It was funny.
When I was called to the stage about thirty minutes later, I smiled. I knew the content of my talk very well, but instead of launching right into it, I said:
“Before I begin, I want to say to the man and woman I just mooned in the parking lot…you’re welcome.”
The room erupted in laughter.
See, when I was waiting to be introduced, I caught myself scanning the audience. I had been too far away to really tell what the couple in their car looked like, so I started to become paranoid. Who had seen me? Who had they told? What were they saying about me and my rear end? It was ridiculous. One split-second moment of vulnerability was threatening to wreck my composure. So I decided right then I would let everyone else in on the joke.
And it worked. Now we were all laughing at me.
I wasn’t always able to do this. In fact, I didn’t even know I should aspire to this until a mentor I trusted woke me up. One day, after listening to a particularly dramatic and tearful monologue from me, she said, “Amy, you really need to stop taking yourself so seriously.”
I remember looking at her like she was insane. Stop taking myself so seriously? What the hell did that mean? Did she not hear everything I was going through? Did she not see the seriousness of this situation? I was offended. Then angry. Then crying again.
I had proved her point for her.
Up to that point in my life, every feeling I had, every mistake I made, every moment of embarrassing vulnerability was like a stab to my fragile ego. Rather than laughing things off or seeing my circumstances as normal and expected, I turned everything into a drama.
As I slowly grew out of this—with the help of my mentor and friends—I began to see how laughing at myself freed me. It allowed me to try new things without as much fear of failure or error. What about you? Can you laugh at yourself or are you the star of your own soap opera?
Eventually, laughing at myself allowed me to bring others into the joke too. Letting other people laugh at me has been one of the best choices I’ve ever made.
But today, I know that when I make a mistake or moon an audience (because believe it or not, I’ve accidentally done that on stage too—another story for another time), I know that I have the last laugh. And it’s a hearty, healthy laugh at the feeling of being free to be myself—no matter how many times I mess up.
As entrepreneurs, we often take our goals and dreams very seriously. But are you letting others laugh with you? Or are you afraid to let people see your humanness? Today, share your embarrassing story and laugh at it—then give others permission to laugh along with you. Trust me, it’s even more freeing than the wind in West Texas.
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