What If You Can’t Make a Mistake?

A reflection on failure, growth, and the moments that shape us.

I can still feel the air in the room.

Top floor. Polished wood. A hint of formality that never really lets you breathe easy. Across the table sat the CHRO—one of the most influential leaders in the company. I had a deck in front of me, slides carefully arranged. I’d practiced my words. I was stepping into a new role, having just moved from recruiting into the world of organizational development. It was my first major initiative—our company’s inaugural Culture Day. And I was about to present the plan.

We were celebrating the one-year anniversary of launching our new company culture. The year before, we introduced it to senior leaders. Now we were scaling the celebration globally—to 90,000 people across dozens of countries, in one single, synchronized moment. This was more than a feel-good event. It was about momentum, visibility, and legacy. It was about showing the world—and ourselves—that this culture wasn’t just words on a wall. It was alive.

Two HR leaders were driving the strategy. I was in a support role, managing the day-to-day execution and working with a team of consultants. Still, I felt the weight of it. I wanted to do this well. I wanted to belong in the room.

So I prepared. The deck I brought wasn’t light. It was structured, strategic, and well thought-out, framing key themes, outlining our goals, and surfacing early designs and activation ideas. It reflected careful coordination and clear ambition.

But what he needed was something else.

He needed specifics—detailed progress updates, decision points, and clear next steps. He already had the vision—he’d been shaping it alongside the CEO from day one. What he needed now was evidence that we were fully in execution mode—that the plan was tight, the risks understood, and the timeline mapped.

What I had brought skimmed when he needed to dig. It conveyed promise, but not precision. And in that gap, I felt myself shrink.

The meeting ended without alignment. No drama, no explosions—just a quiet, unmistakable sense that I hadn’t delivered what the moment required.

And for weeks afterward, I carried that weight.

How did I misread the ask?
Why didn’t I push harder for clarity upfront?
Why didn’t I anticipate what someone at that level would need to feel trust?

I told myself I’d made a mistake. A big one.

But here’s what I see now: the mistake wasn’t what I brought to the table. The mistake was the story I told myself afterward—that I wasn’t ready, that I didn’t belong, that one misstep defined my worth.

What if I had it all backwards?

What if I hadn’t made a mistake at all?                                            What if this—this exact moment—was how I was meant to learn the language of executive leadership?
What if this was my training ground, not my failure?

We grow not just by getting things right, but by facing the discomfort of misalignment and letting it sharpen our awareness. That meeting taught me more than any “success” could have. I learned how to read the room—not just emotionally, but operationally. I learned that strategic storytelling must be paired with concrete delivery. I learned how to prepare for different types of stakeholders, not just different levels.

I also learned how easy it is to turn a lesson into shame—and how hard it is to unlearn that reflex.

Because most of us were conditioned to believe that mistakes signal weakness. Especially early in our careers. Especially as women in leadership. Especially when you’re new to the room and trying to earn your place at the table.

But what if the opposite is true?

What if those moments—those uncomfortable, unsatisfying, awkward moments—are evidence that we’re in the arena? That we’re stretching? That we’re becoming?

You don’t build a meaningful career—or a meaningful life—by avoiding mistakes. You build it by moving. By showing up. By learning out loud and evolving in real time. By seeing “mistakes” not as detours, but as part of the path itself.

I look back at that meeting now and think: good. I’m glad it happened. I’m glad I had that experience early, when I could absorb the lessons and integrate them into everything that came next.

And still—there were times I slipped back into old patterns. Times I polished when I should have clarified. Times I second-guessed instead of asked. Growth isn’t a straight ascent. It’s waves. We relearn what we already know, over and over, each time with a little more grace.

But I never forgot the core truth I uncovered that day:
That a leader’s job isn’t just to present—it’s to connect.
Not just to inspire—but to deliver.
And not just to get it right—but to be real enough to get better.

So now, when I hear the voice of self-doubt whisper, “Are you sure you’re ready?”—I answer differently.

I remind myself: you don’t have to be perfect.
You just have to be willing.

Because if you’re willing to reflect, willing to adjust, willing to grow—then nothing is wasted.

And maybe, just maybe…

you can’t actually make a mistake.