a young waiter carrying a tray and all the dishes fall

Simple Story Tip #4: Show Off with Failure

The #Humblebrag is the most appealing and effective way to get people to believe you are awesome while also liking you.

It works so simply: Tell a story of a time you really messed up.

Like, colossally.

Mine: I lost $9M of investor money in a failed startup by being a lousy CEO.

The more painful and truly embarrassing the story the better. Get into the details. Explain precisely how badly you messed up. The consequences for others. The shame and humiliation you felt.

But, then… Explain how much you learned.

Talk about the steps you took to make sure that wouldn’t happen again.

You can literally just list out all of your amazing skills now. Walk the audience through the wonderful things you know how to do.

You’ve got them. They feel for you. And they trust you.

They know you won’t mess up again. And you have the capacity to learn and grow.

Compare that to the opposite. Just telling them how awesome you are without the failure story. You’d sound like an arrogant jerk who is so up your own butt you can’t learn a thing. Failure! It’s the secret weapon in the master storyteller’s arsenal.

Share the Post:

Related Posts

Subscribe to Our Strategic Storytelling Newsletter

Learn the secrets of strategic storytelling and see great examples of business storytelling done right (and sometimes: done very, very wrong)
a charcoal drawing of a pocket compass