The Most Common Question I Get From CEOs (That They Never Say Out Loud)

To their teams, investors and customers, they operate with confidence. They’re decisive, strategic, fluent in all things business. They present vision decks, lead town halls, close funding rounds and say the right things on podcasts.

But in the quiet of a one-to-one? When the room is closed, the mask is off and no one’s taking notes?

The most common question I hear is:

“Am I the only one who feels like this?”

Not “this” as in confusion or incompetence, they’re not flailing. These are exceptional leaders. They’ve built companies, scaled teams, delivered results. They’re high-functioning, high-performing… and quietly asking if it’s all still worth it.

What is this?

It’s the creeping question about meaning. About energy. About whether they still want the life they’ve built. It’s wondering if the relentless pace, the constant demands, the lonely decisions… are actually sustainable.

And here’s the thing: they rarely say it out loud first.

But when I do, when I gently name it, there’s this visible shift.


A pause.

An exhale.

That exhale? That’s where the real work begins.

Because it’s not weakness. It’s awareness.

It’s the point where they stop performing leadership and start inhabiting it.

It’s where strategy meets self. And from there, everything gets sharper.

This is what coaching often looks like at the highest level.

Not rescue. Not therapy. Not a magic fix.

But a place to think clearly. Honestly.

To stop pretending and start leading with more conviction, more clarity and more humanity.

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What They Don’t Tell You at the Top Table

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Writing a Book While Parenting, Working and Not Losing My Mind (Completely)