What Taylor Swift, Mark Cuban and Michael Jordan Can Teach Us About Embracing Failure Failure is not a four-letter word; it's a stepping stone to success

By Craig Kielburger

Key Takeaways

  • The ability to face failure with resilience can be more valuable than an MBA, a long list of business contacts or seed funding.
  • It's time we shifted our thinking and embraced failure as a valuable teacher who equips us with the essential business and life skills that lead us to success.
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Success is a word that resonates with us all. It's the fulfillment of our goals and dreams, and, for entrepreneurs, it typically means the pay-off associated with creating a popular and profitable product or business. As a society, we celebrate those who reach the pinnacle of success, but we tend to overlook the bumpy road they've traveled to get there — one that's often filled with failures, disappointments and countless setbacks.

Becoming an entrepreneur usually means failure is less of a possibility so much as a virtual certainty. So, entrepreneurs must be resilient and learn to overcome rejections, obstacles and outright failure to realize their dreams.

In Silicon Valley, for example, failing (often spectacularly) is not only accepted but is often celebrated as a rite of passage in the journey to success. There are dozens of entrepreneurs who had to hit rock bottom before they bounced back.

Steve Jobs was famously fired by the board of the company he started before mounting a comeback and turning Apple into one of the world's most profitable and innovative companies. Before co-founding PayPal and becoming a billionaire, Peter Thiel managed a hedge fund called Clarium Capital. Launched in 2002, it grew to $8 billion in assets but faltered in the wake of the 2008 recession and lost 90% of its value by 2010.

Related: 6 Things You Gain By Embracing Failure

American billionaire and television personality Mark Cuban famously quit or was fired from his first three jobs after university. However, one of those experiences led him to start his own computer systems company, MicroSolutions.

"It doesn't matter how many times you strike out," he wrote in How to Win at the Sport of Business: If I Can Do It, You Can Do It. "To be a success, you only have to be right once. One single time and you are set for life."

Of course, embracing failure as a necessary step toward success extends beyond business. Widely regarded as the greatest basketball player of all time, Michael Jordan emphasized the pivotal role of failure in his career. Despite a track record that featured five MVP awards, six NBA championships and numerous records and scoring titles, he cites failure as a necessary ingredient of his success.

"I've missed more than 9,000 shots in my career. I've lost almost 300 games. Twenty-six times, I've been trusted to take the game-winning shot and missed. I've failed over and over and over again in my life. And that is why I succeed," Jordan wrote.

Related: Why Success Makes No Sense Until You Embrace Your Failures

Or consider Taylor Swift, who has become one of the most successful artists of her generation. She, too, has acknowledged that luck and failure were stepping stones towards her unparalleled successes. In fact, in her 2023 iHeartRadio Innovator Award acceptance speech, she encouraged young people not to overreact to failure, emphasizing its role in shaping her journey to success.

"You have to give yourself permission to fail. I try as hard as I can not to fail because it's embarrassing, but I do give myself permission to, and you should, too," said Swift.

Having worked with teachers and young people for decades, I believe Swift's message to her fans is powerful and necessary. For too long, I've seen our education system instill an aversion to failure, treating it as something we should be ashamed of instead of celebrating.

I was fortunate to learn difficult lessons about failure at a young age. When I was 12, I started a charity called Free the Children, which I launched with the help of family and friends after reading about kids my own age forced into slave labor in Southeast Asia.

Initially, our organization focused solely on freeing enslaved children by literally breaking down factory doors and leading them to safety. In our minds, we were successful because we thought we were forever changing the lives of these children by freeing them from factories. But inevitably, a few months would go by, and we would see the same children back in a different factory, having been returned by their families or whoever was controlling them.

Related: How to Recover From Your First Failed Business

We failed because we didn't understand the root causes that led those children to be there in the first place. Their families were desperately poor, there were no schools, and they had little in terms of food, healthcare or clean water. These underlying conditions were what led to the children ending up in forced labor.

So, from those initial failures, we learned that we had to shift our thinking and start addressing the conditions that forced families to give up their children. This led us to create an innovative five-pillar model that provided educational opportunities, clean water sources and income opportunities for families to become financially self-sufficient. In doing so, we leveraged our initial failures into a much greater success that has benefitted thousands of children across the developing world.

The ability to face failure with resilience can be more valuable than an MBA, a long list of business contacts or seed funding. Failure is not a four-letter word; it's a stepping stone to success. It's time we shifted our thinking and embraced failure as a valuable teacher who equips us with the essential business and life skills that lead us to success.

Craig Kielburger

Entrepreneur Leadership Network® Contributor

Social Entrepreneur and New York Times Bestselling Author

Craig Kielburger is a social entrepreneur and New York Times bestselling author who has found success scaling and operating organizations across multiple sectors. For 25+ years he's worked with companies, thought leaders, entertainers, educators and youth to help them create a living legacy.

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