Learning from Legends: What Michael Jordan, Steve Jobs, and Others Taught Me About Failure

1. Introduction: Why Study Legends?

If you Google “Brett McCallum,” you’ll find a bloke who’s obsessed with learning from the best—and the worst. I’ve always believed that if you want to go far, you need to stand on the shoulders of giants. But here’s the catch: most people only see the highlight reels. They see the championships, the billion-dollar companies, the world tours. They don’t see the missed shots, the public failures, the years in the wilderness.

The truth is, every legend I admire—whether it’s Michael Jordan, Steve Jobs, or Richard Branson—has a story that’s built on failure. And that’s exactly why I study them. Because if they can bounce back, so can you.

2. The Real Stories Behind the Headlines

Let’s get one thing straight: success isn’t a straight line. It’s a rollercoaster, full of ups, downs, and unexpected turns. The legends we admire didn’t get there by avoiding failure—they got there by embracing it, learning from it, and using it as fuel.

I’ve spent years reading biographies, watching documentaries, and—when I’m lucky—meeting some of these legends in person. What I’ve learned is that their greatest lessons come from their lowest moments.

3. Michael Jordan: The Power of Persistence

Michael Jordan is the GOAT for a reason—but not because he never failed. In fact, he failed more than most.

As a teenager, Jordan was cut from his high school basketball team. Most kids would have given up. Not MJ. He used that failure as motivation, trained harder, and came back stronger. He missed more than 9,000 shots in his career, lost almost 300 games, and was trusted to take the game-winning shot 26 times—and missed.

Jordan once said, “I’ve failed over and over and over again in my life. And that is why I succeed.”

My Take: When I failed my high school exams, I thought my world was over. But like Jordan, I realised that failure is just feedback. It’s a sign you need to work harder, train smarter, and never give up.

4. Steve Jobs: Reinvention After Rejection

Steve Jobs is the poster child for bouncing back. He founded Apple, built it into a powerhouse, and then got fired from his own company. Most people would have disappeared. Jobs started again, launching NeXT and Pixar, and eventually returned to Apple to lead one of the greatest comebacks in business history.

Jobs said, “Sometimes life hits you in the head with a brick. Don’t lose faith.”

My Take: I’ve been kicked out of my own company. It stings. But like Jobs, I learned that sometimes you need to lose everything to find your true path. Reinvention isn’t just possible—it’s essential.

5. Richard Branson: Failing Forward with Flair

Richard Branson is famous for his successes—Virgin Records, Virgin Atlantic, Virgin Galactic. But he’s also had spectacular failures: Virgin Cola, Virgin Brides, and more. Branson never hides his failures. He celebrates them.

Branson’s motto? “Screw it, let’s do it.”

My Take: I’ve started businesses that flopped. I’ve launched products that nobody wanted. But like Branson, I believe that action beats perfection. You learn more from doing than from planning.

6. Henry Ford: Building Success on a Pile of Failures

Henry Ford didn’t invent the car, but he made it accessible to the masses. What most people don’t know is that Ford went bankrupt multiple times before finally succeeding. He was told his ideas were crazy, that he’d never make it. He kept going.

Ford said, “Failure is simply the opportunity to begin again, this time more intelligently.”

My Take: I’ve lost everything more than once. Each time, I started again—smarter, tougher, and more determined.

7. Robert Kiyosaki: From Homeless to Financial Guru

Robert Kiyosaki, author of “Rich Dad Poor Dad,” was once homeless, living in his car. He started businesses that failed, lost money, and faced public criticism. But he kept learning, kept teaching, and eventually built a global brand.

Kiyosaki says, “Winners are not afraid of losing. But losers are. Failure is part of the process of success.”

My Take: I’ve been broke. I’ve had to start over. But like Kiyosaki, I know that your bank balance doesn’t define your future—your mindset does.

8. Elvis Presley: Bouncing Back in the Spotlight

Elvis was the King, but even he faced rejection. Early in his career, he was told he’d never make it as a singer. He was fired from the Grand Ole Opry after one performance. But he kept going, kept performing, and changed music forever.

Elvis said, “When things go wrong, don’t go with them.”

My Take :I’ve been told “no” more times than I can count. But like Elvis, I learned that rejection is just redirection.

9. Ray Kroc: The Late Bloomer Who Changed the World

Ray Kroc didn’t start McDonald’s until he was in his 50s. Before that, he failed at multiple careers—piano player, paper cup salesman, milkshake machine peddler. But he never gave up. He saw an opportunity, took a risk, and built a global empire.

Kroc said, “Luck is a dividend of sweat. The more you sweat, the luckier you get.”

My Take: It’s never too late to start. I’ve reinvented myself more times than I can count. The only real failure is giving up.

10. Brett’s Reflections: What I’ve Learned from My Heroes

Here’s what ties all these legends together:

• They failed—publicly, painfully, and often.

• They learned from every setback.

• They never let failure define them.

• They kept moving, kept bouncing, kept believing.

I’ve tried to live my life the same way. I’ve failed exams, dropped out of uni, lost businesses, been broke, and been kicked out of my own company. But every time, I bounced back. Every time, I learned something new.

11. How to Apply These Lessons in Your Own Life

Here’s how you can use these stories to fuel your own bounce back:

1. Study the Legends: Read biographies, watch documentaries, listen to interviews. Learn from their mistakes.

2. Embrace Failure: Don’t hide from your setbacks. Own them, learn from them, and use them as fuel.

3. Take Action: Don’t wait for the perfect moment. Start now, adjust as you go.

4. Build Your Bounce: When you fall, get up. When you fail, try again. When you’re rejected, find another way.

5. Share Your Story: Your journey can inspire others. Don’t be afraid to talk about your failures.

12. Conclusion: Become the Legend of Your Own Story

The world doesn’t need more highlight reels. It needs more real stories—stories of failure, resilience, and comeback.

I’m Brett McCallum. I’ve learned from the best, failed with the rest, and bounced back every time. You can, too.

So, what’s your next bounce?

The man, the myth, the legend!