We’ve all heard the line before: “What would you attempt if you knew you could not fail?”

It sounds inspiring, like something you’d find on a poster in a high school gym or on a coffee mug meant to fire you up in the morning.

But here’s the thing: it’s actually a dangerous question.

Why? Because it makes us believe we need a guarantee before we can move forward. It whispers that certainty is a prerequisite for action. That, unless success is inevitable, we’re better off waiting.

And that’s precisely the trap I almost fell into when I set out to write my first book.

The Question That Froze Me

When the idea for The Magic of a Moment first surfaced, I was excited. I had spent decades in higher education, consulting with nearly a thousand institutions, and I had seen firsthand how the smallest moments often carried the most significant weight in people’s lives.

I believed in the message. I wanted to share it. I even knew deep down that it could help others.

But then the question crept in.

What if it doesn’t work? What if I spend months writing and no one reads it? What if I fail?

That familiar line — “What would you attempt if you knew you could not fail?” — made me pause. Because the truth was, I could fail. I could pour my heart into the manuscript and watch it sink without a ripple. I could face rejection from publishers. I could embarrass myself by putting my name on something people might dismiss.

And so, for a time, I hesitated.

The Real Problem With the Question

Here’s why that famous quote is dangerous: it assumes that the absence of failure is the key to courage. It suggests that boldness comes from certainty.

But certainty is a myth.

Ask Walt Disney, who was fired from his first job for “lacking imagination.” Ask Thomas Edison, who tested a thousand times before a single light bulb worked. Ask J.K. Rowling, who stacked rejection letters until one publisher finally said yes.

None of them acted because they knew they wouldn’t fail. They acted because the work mattered more than the outcome.

And that’s the shift I had to make.

Choosing to Write Anyway

One morning, I realized I was asking the wrong question. The real question wasn’t “What would you attempt if you knew you could not fail?”

It was: “What’s worth attempting even if I might fail?”

And for me, the answer was clear. Sharing the stories and insights that had shaped my own life was worth it — even if the book never hit a bestseller list, even if only a handful of people ever read it.

Once I stopped waiting for certainty, the act of writing became lighter. It became less about perfection and more about contribution: less about results and more about meaning.

I sat down, day after day, and the manuscript began to take shape. Some days it flowed. Some days it didn’t. But every day I was in motion, I was no longer stuck in the shadow of “what if.”

Failure Reframed

Here’s the paradox: when you stop demanding guarantees, you actually permit yourself to succeed.

Because every attempt, whether it “works” or not, reshapes you. Writing my first book taught me discipline, clarity, and the courage to pursue my goals. It showed me that I could share my voice and risk being seen.

And when The Magic of a Moment finally made its way into the world, the response surprised me. On day one, it became a #1 International Best Seller. People wrote to me. They told me about the minor adjustments they made as a result of what they read. They shared how a single sentence or story had changed the way they looked at their own lives.

That impact never would have happened if I had waited for certainty.

The Better Question

So here’s the invitation: instead of asking yourself what you’d do if failure wasn’t an option, ask:

• What’s worth doing, even if it fails?
• What would still matter to me tomorrow, even if no one applauded today?
• What’s meaningful enough to try, knowing I might stumble, fall, and get back up?

Those are the questions that matter.

Because the goal isn’t to avoid failure, it’s about building a life where the attempts themselves are meaningful enough to be worth it — regardless of the outcome.

An Exercise for You

If you’re reading this and feeling the pull of something you’ve been putting off, try this:

1. Write down three things you’ve been waiting to attempt until you feel “ready.”
2. For each one, ask yourself: Would this still be worth it if I were to fail?
3. Circle the one that stirs you the most.
4. Take one small step toward it today. Not tomorrow. Today.

Because you don’t need certainty to act, you need movement.

Closing the Loop

That question — “What would you attempt if you knew you could not fail?” — sounds empowering on the surface. But for me, it was paralyzing.

The dangerous part wasn’t the words themselves, but the illusion they carried: that safety comes first, and only then can courage follow.

But courage doesn’t work that way.

Writing my first book taught me this: what matters most is not the absence of failure. It’s the willingness to begin anyway.

And that lesson has carried into every project, every speech, every decision since.

So, don’t wait for guarantees. Don’t wait for certainty. Don’t wait for the absence of risk.

Ask yourself instead: What’s worth attempting even if I might fail?

Then go do that.