A self-made billionaire explains how Britney Spears helped her teach a key business lesson to her employees

It’s not every CEO who plays a Britney Spears song at a company-wide presentation.

But “Oops, I Did It Again” was a key part of a recent meeting led by Sara Blakely, the self-made-billionaire founder and owner of the intimate-apparel company SPANX.

Blakely had organised the presentation around her “oops” moments, or the mistakes she’d made throughout the company’s history. The goal was to communicate to employees that failure can be a good thing because it means you’re trying something new.

“To encourage people to fail, I’m bringing up my failures in front of the team often,” Blakely said in an interview with Business Insider. “I’m always openly talking about it.”

In this particular presentation, Blakely went through a bunch of “oops” moments, some more recent than others, and assigned a theme song to each one. “Oops, I Did It Again” played while Blakely talked about a particular pattern of mistakes she’d made.

Blakely’s celebration of failure stems from her father’s habit of asking her and her brother what they’d failed at that week, when they were kids. If Blakely announced that she’d tried out for something and bombed, for example, “he would actually high five me and say, ‘Congratulations! Way to go!'”

“What it did was just reframe my definition of failure,” she said. “Failure for me became not trying versus the outcome.”

When it comes to her employees, Blakely says it’s important for them to approach their failures from a constructive perspective.

“If there’s a failure or an oops in your life,” she said, “if you learn from it and if you can laugh about it, then it’s all worth it.”

Alana Kakoyiannis contributed additional reporting.

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