Every founder eventually encounters a moment when the path forward appears blocked.

The bank says no.

The investor passes.

That candidate you really wanted declines.

The market shifts.

The numbers don't work.

The opportunity you've been working toward suddenly feels out of reach.

In moments like these, it's tempting to treat the obstacle as a conclusion.

To assume the answer is no - permanently.

To scale back the vision.

To make the situation mean something about you personally as the founder.

Then to abandon the idea and move on.

But one question has shaped more growth decisions, acquisitions, financing discussions, and strategic opportunities in my career than almost any other:

What would need to be true for this to work?

A number of years ago, I was involved in an acquisition that looked dead before it even started.

The company had come off a difficult year. But an excellent opportunity to expand ahead of schedule (through the acquisition of a competitor) came o...