A courageous entrepreneur — Sara Blakely

Sara Blakely, a courageous entrepreneur

Blakely & a friend, from the Spanx.com website

Sara Blakely, the former door-to-door fax machine salesperson who founded Spanx, is one courageous entrepreneur.

Not just because she took her entire life’s savings—$5,000—and gambled it on a product almost no one but her believed in. And not just because she pushed on through the skepticism, cold-called her way into an appointment with the lingerie buyer at Nieman Marcus, and closed the deal while standing in the ladies’ room, showing off her before-and-after butt. I don’t know about you, but even describing those acts of courage caused me to break out in a cold sweat; I can’t imagine actually doing them.

But because Blakely did do all that—and more—the product that created so much initial skepticism is now the, er, “foundation” of a billion-dollar business. [I doubt that’s an original pun; my apologies—E.] And her company is paying forward that $5,000 investment by supporting microloans for women entrepreneurs through its Leg Up program.


“Throughout my entire journey I’ve been afraid. I get nervous a lot; I get anxiety. I still experience all those emotions but it feels self-indulgent to sit back and say “I’m not going to do it…”

That’s from Blakely’s interview on The James Altucher Show podcast. If ruled the world, it would be required listening for everyone who has ever been afraid.

Fear and the courageous entrepreneur

I don’t know about you, but I’ve never felt “self-indulgent” giving into my fears. Relieved? Occasionally. Ashamed? More often. But not self-indulgent.

But then, I don’t think of my work as having a higher purpose. I mean, I can see it does, if I stop to think about it: I help people express themselves more fully and memorably. That’s important stuff. But I don’t often frame it that way; my “higher purpose” hasn’t been at the top of my To-Do list.

Well, it is now.

The other two things that fuel her courage are “immense gratitude” and embracing her own mortality. Like Steve Goodman, a singer whose drive inspired me, Blakely knows just how short life can be; she saw her best friend get run over by a car when they were 16. Surviving something like that leaves you no time for complacency. No wonder Blakely is a force of nature.

For those of us who don’t engage with our fears quite as regularly, it’s easy to forget the payoff. Blakely does it often enough that she’s clear on the benefits of facing her fears:

“I’ve seen how my life expands every time.”

Not afraid to fail

Blakely wasn’t raised to be fearless—not directly. But she was raised to embrace failure. She said her father expected a weekly report of the times she and her brother had tried something and failed. When she bombed out in her cheerleading audition, he high-fived her.

You didn’t grow up like that? Me neither. But we can recreate it for ourselves.

Every Sunday I fill out a chart of my accomplishments during the past week. One of the folks in my mastermind group suggested I should add a V at the top, and post a check mark to show I had done something that made me feel vulnerable. Maybe I’ll add an F up there for vulnerability turned up a notch to fear.

The more I face my fear, the more my life can expand, the more I can fulfill that purpose greater than myself: helping people improve their communication skills. Who knows? Day by day, I might become a courageous entrepreneur, too.

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