Why having a “stupid question” habit accelerates creative thinking

I keep a small ritual: whenever I’m stuck on a problem or drifting through a new topic, I force myself to ask what I’ve come to call a “stupid question.” Not the rhetorical kind—those with obvious answers or meant to be flattering—but deliberately naïve, sometimes embarrassingly simple questions that would make me sound like I’d never learned anything. Over time this habit has felt less like a gimmick and more like a mental floss: awkward at first, then quietly transformative.

There’s a peculiar power in saying aloud what you fear will make you seem foolish. The first time I asked a “stupid” question in a meeting years ago—“Wait, why does everyone say ‘user experience’ instead of ‘how people use things’?”—I braced for silence and subtle eye rolls. Instead, a colleague explained, someone else chimed in with a different angle, and the conversation pivoted into a surprisingly generative discussion that led to a design tweak. That tweak mattered. The “stupid” question had opened a door.

Why the label “stupid” matters (and why to keep using it)

Call it provocative if you like, but tagging a question as “stupid” does something psychologically useful. It lowers the stakes. If I tell myself I’m allowed to ask something ignorant, I give myself permission to bypass pretension and go straight to curiosity. There’s a humility in naming your ignorance openly; it signals to others that you’re not posturing and invites candidness in return.

In groups, that kind of vulnerability is contagious. When one person asks a basic question, others feel safe to reveal their own gaps. Suddenly, what looked like a room full of experts becomes a space for exploration. The exchange that follows often surfaces assumptions everyone was silently operating under—assumptions that can be the real obstacles to creative leaps.

What “stupid questions” actually do in the brain

When you ask an apparently simple question, you disrupt familiar thinking patterns. Neuroscience tells us that creativity requires both divergent thinking (generating lots of possibilities) and convergent thinking (selecting and refining). Stupid questions nudge the brain into divergence. They invite unusual associations by loosening the internal filters that normally censor odd or impractical ideas.

For example, asking “What if chairs were designed to make us nap?” sounds absurd in a furniture meeting. But that sort of question creates mental space for considering comfort, posture, and the emotional affordances of objects—ideas that might otherwise remain siloed. From there, practical innovations—reclining desk chairs, ergonomic hammocks, or new workplace naps policy—become thinkable.

How to cultivate the habit without becoming performative

There’s a difference between genuinely curious “stupid” questions and performative ones designed to get attention. The former comes from a place of real not-knowing; the latter is showmanship. Here’s how I keep mine honest and useful:

Practical places to use the habit

The “stupid question” practice is versatile. Here are some contexts where it accelerates thinking:

Examples that stuck

Some “stupid” questions I’ve asked led to small but meaningful outcomes:

When to hold back

This habit isn’t an excuse to derail every conversation or to be provocative for provocation’s sake. There are times when a “stupid” question is tactless—during someone’s emotional vulnerability, or in meetings where clarity and speed are urgent. Use discretion. Part of creative intelligence is knowing when to explore and when to execute.

A small experiment you can try

Try this for a week:

It’s remarkable how quickly the habit reshapes attention. Once you’ve learned to ask without fear, the world starts to look like a series of puzzles waiting for gentle, earnest interrogation. The phrase “stupid question” then becomes less about shame and more about courage: the courage to say, “I don’t know,” and to let that absence of knowledge become the seed of something new.

As a practice, it’s modest and free. It doesn’t require software, training, or permission—only a willingness to be a little ridiculous. If you’re anything like me, that willingness might be the most efficient shortcut to thinking in new ways.