Normalizing stupid

“This might be a silly question, but…”

“That’s not a silly question at all”

A profoundly compassionate and subtle thing we can do for each other in conversations is to gently puncture notions of shame and fear that arise.

An example we often see is the “This might be a silly question, but…” preface to a question. It’s so commonplace that we rarely acknowledge it, but noticing it might be worth your time.

When we create a space for the underlying fears that direct the flow of our emotions to be seen for what they are—psychological suffering that can be overcome—we free ourselves to show up more fully and honestly in the moments when we’re fearful.

A quick “That’s not a silly question at all” before responding might be all that’s needed.


When I was a bright-eyed and clueless freshman at Florida State University, I used to correct friends of mine when they made mistakes around me. Typographical error? Not on my watch. Factual error, however trivial? I’m on the job—thank me later!

For me, the motivation to correct them was obvious: how could someone not want to know when they’re wrong about something? I wished more people pointed out my mistakes when I made them. I asked them to!

Sadly, this is not actually how humans work.

I learned that my habit of correcting people made them extremely uncomfortable. I was blind to the effects of my “goodwill” until some generous souls pointed out how the corrections made them feel. I hadn’t for a moment considered the possibility that there weren’t people who didn’t want to aggressively participate in their own personal development.

I was so naive.

What I was actually exhibiting was an act of breathtaking self-absorption. Not only did I assume that everyone thought about things like me, I proceeded with the solutions without their approval or consent. I did not, as it turns out, have all the answers.


Over time (and many re-readings of good books), I’ve learned how to better communicate with and relate to humans. I’ve noticed the ways in which fear and shame are baked into my own mental models and patterns of thought. I’ve observed how varying degrees of anxiety is crippling generations of leaders and thinkers and world-changers.

It’s sobering, and puts many of our perceived struggles in perspective: the suffering most people reading this post experience is psychological.

This realization—coming alive to me in ways that it never did before—helps me better understand a host of other things more clearly. Perhaps most closest to home, it helps me understand why so much of Seth’s writing is about fear and the lizard brain and the emotional component of business.

This is curious because Seth is one of the most frighteningly adept business minds I’ve ever encountered. I’m not into hero worship, but the man is a monster. And this mental dexterity is wrapped in an immense and unwavering kindness and generosity.

And contrasting this with my juvenile intentions as a 22 year-old undergrad crystallizes nearly a decade of learning that will continue to pay dividends as I continue to evolve.

Here’s to stupid questions.

Willie Jackson is a Diversity, Equity and Inclusion (DEI) Consultant & Facilitator with ReadySet, a boutique consulting firm based in the San Francisco Bay Area. He is a frequent writer and speaker on the topics of workplace equity, global diversity, and inclusive leadership. Connect on LinkedIn or get in touch.

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