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What If We Stopped Shutting Down “What If?”

ai & education creativity critical thinking curiosity education high school middle school parenting parenting teens school system self-awareness student mindset student success teen self-leadership Oct 07, 2026

The What-If Game

The “What if” game... universally despised by parents, teachers, and babysitters alike. If you’ve spent much time around children, you’ve probably played it. For parents, it can look like:

“What if dogs could talk?”
“What if everyone could read everyone else’s thoughts?”
“What if I had a submarine that could go in the bathtub?”
“What if you called me in sick to school today?”
“What if I never did homework again?”

As a teacher, it usually looks like students trying to take you off track—to avoid the work or the new learning. At least, that’s often the assumption. And the What-If Game rears a particularly nasty head when it’s time to go over lockdown procedures. There is quite literally no end to the possible what ifs in an emergency situation.

As parents and teachers, the game can feel exhausting. There is no winning, and there is no natural conclusion. One answer simply creates the conditions for another question.

But here's what I wonder:

What if that’s exactly the point?

 

We Spend a Lot of Time Teaching Kids to Stop at the Answer

School curriculum necessarily deals in questions with endpoints.

What is 7 × 8?
Balance this chemical equation.
Justify your answer with evidence from the passage.

There is information a student needs to know. There are skills they need to master. And sometimes, there really is a correct answer. But if we’re not careful, students can begin to learn something else alongside all that content:

The purpose of a question is to arrive at the answer.

Once you have the answer, you’re done. Put your pencil down. Turn off your brain. It is what it is.

Except that’s not how most interesting thinking works. An answer can also be the beginning of the next question. In fact, that’s how progress is made.

Okay, but why?
What would happen if we changed this?
Does that always work?
Who decided that?
What would have to be true for the opposite to happen?
What if...?

This is where curiosity starts doing something far more interesting than retrieving information.

It starts creating possibilities.

 

The Silly Questions Might Be the Most Important Ones

I have a rule in any classroom I have ever walked into: There is no question too small or too silly. No question is a waste of my time as a teacher, so ask away.

Why?

Because we adults tend to assign value to questions based on their usefulness.

What if I don’t get into the college I want?

Important.

 

What if I choose the wrong career?

Important.

 

What if humans had tails?

Not particularly useful.

And yet, I’m not convinced usefulness should always be the goal. There is something cognitively freeing about asking a question that has absolutely no practical consequence.

So, what if humans did have tails?

Would chairs need holes in the back? Would pants be designed differently? Would our tails communicate emotion like a dog’s? Would it be rude to touch someone else’s tail? Would we decorate them? Would there be tail charms? Would different cultures develop different rules around them?

Now we’ve moved from anatomy → engineering and design → communication → social norms → culture, all because we entertained an objectively ridiculous question.

Nothing was at stake. Nobody was being graded. There wasn’t a correct answer hiding somewhere that the student was supposed to find.

Their only job was to think. And perhaps that’s exactly why silly questions matter.

 

What If Creates a Mind With More Than One Door

When a student becomes accustomed to looking for the answer, they can become very good at following an established path.

“What if?” asks them to create another one.

Psychologists often distinguish convergent thinking—narrowing possibilities toward a solution—from divergent thinking, in which we generate multiple possibilities or approaches. Divergent thinking isn’t synonymous with creativity, but it is an important component of creative cognition.

The What-If Game gives us a remarkably simple way to practice it.

Take something we assume is fixed. Change one condition. Follow the consequences.

What if there were no grades?
What if you couldn’t use money?
What if humans lived for 300 years?
What if nobody could lie?
What if you had to solve this problem without using the method your teacher taught you?
What if we had spaghetti for fingers? (A favorite from my four-year-old nephew.)

Suddenly, the mind has to leave the familiar route.

And that’s a capacity worth developing.

 

Serious What Ifs Matter Too

Of course, not every “what if” needs to be about spaghetti fingers.

Some of the most powerful questions a teenager can ask are about their own life.

What if I’m wrong about myself?
What if I’m actually not bad at math?
What if everyone else isn’t as confident as they look?
What if I tried and failed?
What if I asked for help?
What if I don’t actually want the future I’ve been working toward?
What if there’s another way to do this?

Those questions create possibility, too.

A student who believes I’m lazy has reached a conclusion. A student who asks, What if I’m not lazy? What else could explain why I keep avoiding this? has reopened the investigation.

That’s an important difference.

Certainty closes doors. Curiosity opens them.

Curiosity generates possibilities. Critical thinking evaluates them.

We need both.

 

Adults Have to Resist Being the Answer Key

This may be the hardest part. A teenager asks us a question, and because we know—or think we know—the answer, we give it to them. How efficient. How helpful. Conversation over.

But sometimes the better response is:

“What do you think?”

Or even better:

“Okay. What if?”

Follow them into it. Let the idea get ridiculous. Ask another question. Allow a conversation to wander somewhere neither of you expected it to go.

You don’t have to turn it into a lesson.Actually, I’d argue that lots of times you shouldn’t. Curiosity doesn’t always need an educational objective attached to it.

Wondering is enough.

 

We Need Kids Who Can Imagine What Doesn’t Exist Yet

I’ve been thinking about this more as AI becomes increasingly capable of giving us answers.

Our kids will have extraordinary access to information. They’ll be able to retrieve facts, summarize ideas, generate possibilities, and solve many kinds of problems with tools more powerful than anything we had growing up. Sidebar: Have you ever tried to explain TV static to someone born after 2008? Their life experience is so different from ours!

All of this makes me increasingly interested in something else:

What will they ask?

Can they notice an assumption when they see one?

Can they imagine an alternative?

Can they look at something everyone else accepts and wonder whether it has to be that way?

Can they encounter a problem without an obvious solution and remain curious long enough to explore it?

Can they ask a question nobody handed them?

Perhaps one of the most important things we can preserve in young people isn’t simply their ability to find answers, but their willingness to keep wondering.

So the next time your student starts:

“Okay, but what if...”

Maybe don’t end the game quite so quickly.

Ask them what they think. Make the scenario stranger. Add another variable. Follow the question somewhere completely useless. Laugh. Wonder. See what happens. Because the What-If Game was never really about getting to the answer.

It was about discovering how many places a mind can go when nobody tells it where it has to end.

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