The Question That Changes Everything

In 1989, a coach named Dan Sullivan started asking his clients a strange question.

These weren't ordinary people.

They were entrepreneurs running 7 and 8-figure businesses. People who had already “made it” by most standards.

And yet, many of them felt exactly like my friend at that lunch:

Successful on paper. Directionless underneath.

Sullivan would sit them down and ask:

“If we were meeting here, 25 years from today — and you were looking back over those 25 years — what has to have happened, both personally and professionally, for you to feel happy with your progress?”

Read that again. Slowly.

25 years.

Not 90 days. Not a year. Not a 5-year plan.

Twenty-five years.

At first, it seems absurd.

Who can think that far ahead? The world changes. Circumstances shift. How can you possibly plan for something 25 years away?

That's exactly why it works.

When you think in decades, something strange happens.

The urgent becomes irrelevant.

The trivial falls away.

What's actually important rises to the surface.

Suddenly, you're not thinking about inbox zero or morning routines or which productivity app to use.

You're thinking about:

• Who do I want to become?
• What relationships actually matter?
• What would I regret not doing?
• What does a life well-lived actually look like — for me?

This is the question nobody asks.

Because it's uncomfortable.

Because it forces you to confront the gap between where you are and where you actually want to be.

Because once you see it, you can't unsee it.

But here's the gift:

Once you answer it, everything else gets easier.

Your habits stop being random checkboxes.

They become votes for the future you're building.

Every morning routine, every workout, every hour of deep work — suddenly connects to something bigger.

You're not just tracking habits.

You're building a life.

There's just one problem…