Ask the Questions That Get You Lost


Kelly Hudson

August 25th

Creative Wayfinding:
Asking Unanswerable Questions

Last week, I was interviewed on High Velocity Radio about Creative Wayfinding. Somewhere in the middle of trying to explain the third wayfinding practice—Ask Unanswerable Questions—I said something I hadn't planned to say:

“Ask the questions that get you lost.

I've been thinking about that ever since. From a very young age, most of us are taught to ask questions that seek answers—right answers, and wrong answers. Questions like, What should I do next? and What's the right decision? and How do I do that?

These are useful questions. We need them, and encounter them daily. But they're also questions that assume an answer. We tend to ask questions with the belief that they'll lead us to a destination. An outcome. A plan of action.

But creative work rarely works that way. Neither, for that matter, does life.

Sometimes the most important questions aren't the ones that show us the way forward. They're the ones that lead us away from the path we already know

What if I don't know what this is yet?

What am I assuming that might not be true?

What wants to happen here that I haven't made room for?

What would I explore if I didn't need to know where it was going?

What becomes possible if I stop trying to solve this?

These questions don't necessarily give us answers. They give us somewhere to wander.

And wandering is a vastly underrated part of creativity.

When we stop trying to arrive somewhere, we begin noticing things we couldn't see from the path: an unexpected connection, a strange possibility, a question beneath the question, a little flicker of energy pointing somewhere we hadn't thought to go.

We get lost.

And getting lost is exactly how we find our way somewhere new.


A Creative Wayfinding Practice

Bring to mind something you're currently trying to figure out.

A piece of writing. A decision. A problem in your work. A transition. An idea that hasn't quite taken shape.

Notice the questions you've been asking about it.

Then try asking a question that doesn't know where it's going.

Not, What should I do?

But perhaps:

What am I curious about here?

What haven't I considered?

What would surprise me?

What don't I know?

What question am I reluctant to ask because I'm afraid of where it might lead?

Don't rush to answer it.

Carry it around for a while.

See what you notice.

Let the question get you a little lost.


This idea emerged during my conversation with Lee Kantor on Business RadioX's High Velocity Radio, where we talked about Creative Wayfinding, uncertainty, leadership, imagination, and what becomes possible when we're willing to leave the map behind.

Listen to the full conversation: “Leave the Map Behind: Finding Your Way Through Creativity & Uncertainty.”

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