Failure #4: The Dinner Table Question That Built a Billionaire

I was recently listening to a podcast with Sara Blakely. For those who don’t know, Sara is the self-made billionaire founder of Spanx. According to Sara’s interview, when she was a kid, her dad had a peculiar dinner table tradition.

Every night, as the family gathered to eat, he’d turn to Sara and her brother and ask one simple question:

“What did you fail at today?”

Not “What did you achieve?” Not “What did you get right?”

But: What did you try that didn’t work out?

He was never disappointed with how they messed up. He was only disappointed when they didn’t have an answer.

Of course, to most parents, failure is something to avoid, fix, or protect your kids from. But not Sara’s dad. He was rooting for it. For Sara’s dad, failure wasn’t an example of her falling short. It was an example of her trying hard. Pushing herself. Attempting to accomplish big and important things.

Imagine what it might have been like having your parents constantly asking you about failure. How would it have changed your relationship with experimentation, trial and error, and uncertainty?

I have to imagine the question from her day rewired something in Sara’s brain. Unlike most children, rather than seeing failure as evidence she wasn’t good enough, she would have learned to see it as proof she was learning. It was permission for her to experiment, take risks, and, most importantly, to keep going when something didn’t work.

And, of course, decades later, that mindset turned into a billion-dollar outcome.

The story is wildly impressive. Sara Blakely founded Spanx with $5,000 and no business background. She got rejected by every manufacturer she pitched. She got laughed at by buyers. She didn’t even have a proper prototype. But she kept experimenting, taking risks, and pushing forward until one of those failures finally turned into a yes.

Today, she’s one of the youngest self-made female billionaires in history.

And it all started with a question about what didn’t go right.

Why Failure Is the Beginning, Not the End

Most of us don’t have someone asking us to talk about failure at dinner. As a result, we learn to hide our struggles. We downplay our mistakes, avoid risks we’re not sure we can win, and edit the messy parts out of our stories.

But failure isn’t the thing to hide from. That’s the real trick here.

To be clear, I don’t mean it’s easy or enjoyable. I’m sure Sara didn’t love being told no. Heck, I’m guessing she didn’t love telling her dad about all her screw-ups. And you don’t have to enjoy any of that stuff, either.

Learning to fail isn’t about embracing and failure. It’s about building the emotional muscle to navigate it in productive ways over and over and over again.

The real reason Sara succeeded isn’t because she embraced failure. She wasn’t running around saying, “Yay! Let’s see how much we can screw up today!” And that’s not what her dad was telling her to do, either.

The first step of learning to fail is simply learning to accept you’ll get things wrong, and that’s OK.

And I’m sharing Sara Blakely’s story because it’s a great example of this small but important nuance. She was conditioned to expect failure and to keep going anyway.

You need to learn to expect it to. That’s your competitive advantage. Trying consistently, courageously, and imperfectly is how you go from a kid at the dinner table to a founder with your own empire.

– Dr. D