The Best Leadership Newsletter Ever

The Best Leadership Newsletter Ever

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The Thing You're Actually Afraid Of

The thing you're worried about is never the thing you're afraid of. This prompt finds the fear is three questions down. This promptuncovers the fear hiding

Aug 25, 2026
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One of my CEO clients told me last month that he was worried about their Series B raise.

They’d already raised a pretty hefty Series A (an amount that rhymes with “men tillion”), they had at least a couple years of runway left and their product was headed in the right direction. Needless to say, I was a bit surprised to hear about the worry.

I asked him what he was afraid of.

“If we can’t raise the money,” he said. “I’d have to lay people off.”

And so….?

“They’d think I failed them,” he admitted.

OK. And what if they did think that?

He paused. He either had to think about that one or had to consider how vulnerable he was ready to be.

And then he spoke.

“I guess it would mean that maybe I’m not actually good at this after all. Maybe I’ve just been lucky.”

Ka-POW!

That’s it. That’s the whole thing.
A five minute fear-of-funding conversation finally revealed the real feelings: He feels like a fraud.

That’s how it always goes in almost every one of my executive coaching relationships.

The thing you’re worried about is never the thing you’re afraid of.

The worry is just the symptom. The deadline, the conversation, the number - none of that is the actual fear.

The fear is three questions down.
It’s hiding in a dark corner and hoping you won’t notice it’s there.

But it is.

And the sooner you uncover it, the more confident you’ll feel.
And the more productive you’ll be.

This prompt dives down and finds the fear underneath the worries.

Strap on your seatbelt.
We may hit some turbulence as we descend into your psyche.

Run the prompt. 👇🏽👇🏽

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