The Best Leadership Newsletter Ever

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🤖 AI Prompts

The Question Most Successful People Avoid

Most successful people can tell you what they gained. Few can tell you what it cost them. This prompt helps you do the accounting.

Jun 30, 2026
∙ Paid

Success has a price.
The problem is that we always make it sound worth it.

We talk about the climb. The grind. The sacrifices nobly made in service of something bigger.

But that’s closer to a Disney dream than reality.

Trevor Noah talks about the loneliness.
Jerry Seinfeld talks about the perpetual dissatisfaction.
Elon Musk talks about the stress and isolation.

Robin Williams and Matthew Perry… well… they can’t talk about it any longer.

I had a leadership coaching client last year who was successful by every external measure. In the middle of our call, she stopped and said: “I don’t think I know who I am outside of this job anymore.”

It wasn’t a complaint. It was a discovery.

That’s what this prompt is about.

Not whether you’re successful.
Not whether the sacrifices were necessary.

But whether you’ve ever actually figured out what you’ve sacrificed to build the life you’re building.

Most people never bother to face this. Because reality means sitting with the stuff that’s poking at your unconsciousness.

The only question is whether you’re actually ready to face your truth.
I ran this on myself (as I do all the prompts) and… wow, what a wake-me-up.

Run the prompt below and find out what you’re pushing aside.

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