From Should to Curiosity

Dec 11, 2025

Dear Friends,

One of my teachers, Stephen Levine, used to say, “Whenever you say ‘should,’ you close your heart.”

Most of us carry around a mental model—a story—of how people ought to live, and then we offer that story to others in the form of a should.

“You should get a job.”
“You should exercise.”
“You should be more like this, less like that.”

We get “should on” all the time, often by well-meaning people who don’t realize they’re placing their story on us.

Of course, life needs rules, agreements, and shared structures. But should carries a particular energy.

Should rarely asks questions.
Should isn’t curious.
Should doesn’t think it has much to learn—because should already knows it’s right.

When we speak from should, the other person becomes someone to convince, not someone to understand.

Curiosity and Should

You might say, “Well, my child should clean his room.”
Maybe. But if our goal is a clean room, does shoulding them get us there?

Or does curiosity — exploring why standards matter, listening for what they need —lead to better outcomes?

Are we building connection with someone or just trying to get our way?

The greatest innovators are often people who question society’s shoulds. They invent and create the future, not just the follow the ways of the past.