Is Winning Actually the Point?

Nastia Liukin was never supposed to win.

In gymnastics, power reigns. Explosive strength, clean landings, gravity-defying speed—that’s what the judges are trained to reward. Nastia didn’t fit that mold. She wasn’t the most powerful or the fastest. “I was probably the least athletic person on the team,” she told me on the podcast.

But what she had was something else: artistry. Elegance. Discipline honed in silence. A kind of strength that doesn’t shout. It whispers. And then it wins.

At just 18, she earned the Olympic all-around gold medal. Not by outperforming others on their terms—but by rewriting the terms entirely.

Her story isn’t just about gymnastics. It’s about what happens when you bring a different form of power into a world that doesn’t know how to measure it.

And that got me thinking—again—about how we define success in business.

Winning vs. Success

When I talk to companies, I often make this distinction: Winning is not the same as success.

Winning is points on the board. It’s metrics and KPIs. Revenue, growth, market share. The scoreboard version of progress.

Success asks a different question: Did we do it the right way?

It asks: Did we act with integrity? Did we uphold our values while chasing results? Did we build something worthy of trust?

Take the Wells Fargo scandal in 2016. They won, on paper. Millions of customer accounts opened. Sales goals exceeded. Bonuses paid. Stock price climbing. It all looked like textbook business success.

But behind those numbers was a culture of pressure and deception. Employees were incentivized to open unauthorized accounts to hit aggressive quotas. Customers were misled. Trust was eroded. And when the truth came out, it didn’t just trigger regulatory penalties. It shattered the company’s reputation.

They won by the metrics that companies love to celebrate—until those same metrics exposed the rot beneath.

They won. But they failed.

Because real success isn’t just performance. It’s principle. It’s how you get there that determines whether what you’ve built can actually last.

“The Whole World Was Cheering—And I Didn’t Know Who I Was”

What struck me most in my conversation with Nastia was her honesty about what came after the gold.

“I had achieved my lifelong dream, but I didn’t know who I was,” she said. “I was 18. I hadn’t gone to school, hadn’t done the normal things people my age were doing.”

She moved to New York. Started over. Took college classes. Relearned how to live. “I looked at a graphing calculator and didn’t know what I was looking at,” she laughed. “But I needed that. I needed to remember who I was without the leotard.”

Nastia’s story reminds us: even at the peak, you might find yourself at the edge of reinvention. That’s what makes grace powerful—it’s not just how you win. It’s how you return to yourself after the winning is over.

The Day I Knew TaskRabbit Would Be Successful

I didn’t always know TaskRabbit would win.

The early days were chaotic. We didn’t even have language for what we were building—there was no “gig economy” yet. We were underfunded, overextended, and completely rewriting the way people thought about work.

But I knew we would be successful.

That realization came quietly, with a job posted on the site from a woman in California. She needed someone in Boston. Her son was undergoing chemotherapy at Massachusetts General Hospital. She couldn’t be there, so she turned to TaskRabbit.

The job: Go to the hospital every day for a week. Bring him a warm blanket and a healthy meal. Sit with him for thirty minutes. Let her know how he was doing.

The Tasker who accepted? Another mom.

The bond that formed between these two women—across the country, across different lives—was powerful. They created something more than a transaction. They created trust.

That’s when I knew: this wasn’t just a platform. This was a vehicle for care. For connection. For grace in motion.

Grace Is a Strategy

In business, we’re taught to admire dominance. Loud voices. Aggressive timelines. Scaling at all costs. But grace is its own kind of strategy.

It’s the ability to move precisely, with integrity. To hold to your values while others cut corners. To expand your impact without diminishing your character.

Grace is what makes space for someone else to rise.

Grace is what turns a task into care.

Grace is how you keep showing up when you’ve already won—and still want to matter.

Nastia Liukin didn’t overpower her sport. She transcended it. She redefined what strength could look like. And in doing so, she opened a path for others to follow.

That’s not just winning. That’s success.