Stories About Mistakes and Growth
Some of the most valuable stories in your memoir will come from the times you were wrong, not in dramatic or catastrophic ways, but in ordinary, human ways, when an assumption didn’t hold up or when you made a decision for the wrong reasons.
These stories matter because they show your thinking in motion. They demonstrate that leadership isn’t about having all the answers—it’s about staying open to change when new conditions emerge.
Here’s a strong example from Howard Schultz’s memoir Onward:
“For years, I believed that rapid growth was the clearest sign of success. But after returning to Starbucks as CEO during its decline, I saw how that mindset had led us to compromise quality and culture. I had to admit that I was wrong—and that realization became the foundation for rebuilding the company the right way.”
What belief did you carry for years before something changed your perspective? That story might be more valuable than any success story you could tell.
The value of choosing a different path.
Success is often measured by progress, but progress in the wrong direction can cost more than it gives. Sometimes it takes a moment of crisis to make us stop, and that’s when meaningful shifts can begin. In Thrive, Arianna Huffington describes one such moment, an experience that made her question everything she thought success was:
“I had just returned from yet another business trip when I collapsed from exhaustion, literally hitting my head on my desk. In that moment, I realized success wasn’t just about money or power. It was about well-being, wisdom, and purpose. That fall didn’t make the headlines, but it changed everything.”
Use Real Examples to Make Your Point
Generic leadership advice sounds like this:
“Communicate clearly with your team.”
Instead, a real story sounds like this:
“I realized I was losing my best people not because of salary or workload, but because I was so focused on efficiency that I’d stopped seeing them as individuals. The shift happened in a meeting with my marketing director when she said something that stopped me cold…”
The first version gives information. The second gives understanding.
That’s the difference between teaching principles and sharing experience. Principles are useful, but experience is memorable.
The Outcomes You Didn’t Expect
If you’re wondering which stories or details to include, consider when reality turned out differently from your plans. The outcomes you didn’t expect. The reactions that caught you off guard. The solutions came from unexpected circumstances.
Surprise often signals significance. If something caught you off guard, it probably contained a lesson you didn’t know you needed to learn. And if it taught you something, it can teach someone else something too.
Here’s an example from Bob Iger’s memoir The Ride of a Lifetime that captures the essence of “The outcomes you didn’t expect”:
“I never expected Steve Jobs to call me and suggest that Disney acquire Pixar. At the time, our relationship was still developing, and I thought the idea would come much later, if at all. But that unexpected call led to one of the most defining partnerships of my career. It taught me that staying open to surprise often opens the door to extraordinary opportunities.”