All Leaders Are Failures

There’s a moment every leader dreads. That sinking, stomach-twisting realization that feels like heavy weights around our ankles dragging us deeper into the chilling ocean's darkness: I mishandled that. Maybe it was an impulsive reaction, a decision made in haste, or a conversation where words became weapons instead of bridges. And in that moment, a whisper creeps in, one that haunts every damaged leader—Maybe I’m not cut out for this.

But here’s the truth: ALL LEADERS FAIL.

Not just once. Not just early in their careers. Again and again. The very act of leading—of making decisions, guiding people, and taking responsibility—means failure is inevitable. And sometimes, that’s where the damage comes from.

A leader doesn’t wake up one day feeling hesitant, cautious, or burdened. It builds. A mishandled situation here. A misjudgment there—like blowing up a balloon too much, stretching it thin until it finally bursts in an irreversible pop. Slowly, without realizing it, they start leading smaller. Safer. Trying to avoid another mistake, another wound. They stop stretching, stop taking risks, stop fully stepping into the role they once fought so hard for.

That is the greatest failure of all. Not the mistake itself, but the hasty retreat that follows.

The Weight of Failure

Failure clings like a heavy coat after a storm. You carry it with you into the next decision, the next meeting, the next tough conversation. It makes you second-guess your instincts, hesitate where you used to charge forward. You tell yourself you’re being careful, but in reality, you’re just afraid.

And yet, the best leaders aren’t the ones who never fail—they’re the ones who refuse to be defined by it. They don’t let a moment of weakness become a lifetime of hesitancy.

So, what separates those who grow from failure from those who are damaged by it? The ability to face it, own it, and learn from it.

Owning the Failure: 4 Questions Great Leaders Ask Themselves

Here’s where the real work begins. When you’ve mishandled a situation, don’t just move on. Ask yourself the hard questions. The ones that force you to look in the mirror, not through a window.

1️⃣ If this situation were a chapter in my leadership story, what would the title be?Would it be The Day I Let Fear Win? The Time I Spoke Without Thinking? Or maybe The Moment I Learned What Not to Do? Naming it forces you to see it for what it is—just one chapter, not the whole book.

2️⃣ What belief or assumption did I carry into this situation that influenced my response?Did you assume someone was attacking you? Did you believe silence was safer than honesty? Did you think admitting a mistake would make you look weak? Our responses often come from unspoken beliefs—ones we need to challenge.

3️⃣ If I could go back and whisper one sentence to myself right before I reacted, what would it be?Would you tell yourself to pause? To listen longer? To ask a better question before assuming? There’s power in recognizing what you needed in the moment so you can carry it forward.

4️⃣ What’s the one thing I will do differently next time?Not ten things. Not a complete overhaul of your leadership style. Just one change. Because growth isn’t about grand gestures—it’s about small, deliberate steps in a better direction.

The Failure That Matters Most

The worst failure isn’t making a mistake. It’s refusing to confront it.

It’s allowing one bad decision to make you a hesitant leader. It’s letting a tough conversation convince you to stop having them. It’s choosing self-preservation over self-improvement.

Every leader has their moments of failure. But the best ones don’t let those moments become their identity. They refuse to lead smaller. They refuse to dim their own light. They refuse to let one chapter define their entire story.

So, the next time failure finds you—and it will—don’t retreat. Don’t shrink. Ask the questions, do the work, and keep leading.

Because failure isn’t the end of your leadership journey.

It’s proof that you’re still on it. And if you are a leader developing other leaders, use these questions to help them reframe and learn—because real leadership isn’t about perfection, it’s about growth.

A damaged leader sees failure as a scar. A great leader sees it as a map. Choose to navigate forward.

Natalie’s Notes

Failure has a way of making leadership feel lonely. Not because others disappear—but because shame convinces us we have to carry it alone.

Most leaders I work with don’t struggle because they don’t care. They struggle because they care so deeply. About their people. About getting it right. About not becoming the kind of leader who causes harm. And when they fall short of their own expectations, the inner dialogue turns brutal.

Here’s what I want you to understand clearly:

Feeling the weight of failure does not disqualify you from leadership. It confirms you’re doing the work. The danger isn’t the mistake—it’s what happens next. When failure goes unexamined, it quietly rewrites your identity. You stop trusting yourself. You start leading from defense instead of intention. And over time, you confuse self-protection with wisdom.

But reflection changes that.

When a leader is willing to sit with the discomfort—without spiraling, without self-abandonment—failure becomes data instead of a verdict. It shows you where your values were stretched, where fear stepped in, where growth is still possible.

Leadership isn’t about never missing the mark. It’s about having the courage to look at where you missed it and stay in the game anyway.

So if you’re reading this while replaying a moment you wish you could redo, let this be your permission slip: pause, reflect, repair where needed—and then keep going.

You don’t become a better leader by being flawless.

You become one by being honest enough to learn.

— Natalie