The only truly serious questions

Wild Garden
3 min readJul 11, 2022

I recently took the Big 5 (OCEAN) personality test. It asks you 40+ questions and maps you on a handful of dimensions: openness, conscientiousness, extroversion, agreeableness, and neuroticism.

Though I wouldn’t make a big life decision based on a personality test any more than I would my astrological sign or birth order (I’m a Myers-Briggs INFJ, Libra, and middle child, fwiw), I think the process of self-examination is a worthy and useful exercise.

OCEAN ranks you on a high-medium-low scale of each attribute. My results are high openness, conscientiousness, and agreeableness; medium extroversion and neuroticism. Less relevant than how accurate these are to how people experience me (lots of people would object to my high agreeableness, for instance) is how much they reflect who I’m trying to be.

Neil Young sang that every junkie is like a setting sun and there’s a lot of evidence that our openness also fades faster than it should. Openness is suspension of disbelief. As get get older, our priorities firm, our worlds shrink, and our desire to see order increases.

And it starts young. In A More Beautiful Question, Warren Berger writes:

A recent study found the average four-year-old British girl asks her poor mum 390 questions a day; the boys that age aren’t far behind. So then, it might be said that questioning is like breathing: It’s a given, an essential and accepted part of life, and something that anyone, even a child, can do.

Yet chances are, for the rest of her life, that four-year-old girl will never again ask questions as instinctively, as imaginatively, or as freely as she does at that shining moment. Unless she is exceptional, that age is her questioning peak.

Drawing upon a similar insight, in Milan Kundera writes in The Unbearable Lightness of Being that, “The only truly serious questions are the ones even a child can formulate. Only the most naive of questions are truly serious.”

Lots of us spend the day asking questions. But few of those are naive ones; most of designed to extract a particular piece of information that will help feed a known need.

When is this due?

What’s the budget?

What’s our target audience?

What are the KPIs?

We need these things to keep the trains moving. Consistency and predictability are useful, too.

However, we should complement these with questions that broaden our apertures into the less knowable, as much as it goes against our corporate instincts. Berger writes, “The business-innovation guru Clayton Christensen — himself a master questioner — observes that questioning is seen as ‘inefficient’ by many business leaders, who are so anxious to act, to do, that they often feel they don’t have time to question just what it is they’re doing.”

Kids ask the most inefficient questions imaginable, like whether dinosaurs had pets or if the sun goes down so other people can use it or if their lost tooth is going to heaven (more here). They ask without presupposition or ego, without cultural context or social norms in mind, without an angle. They ask as if the most mind-expanding piece of information just hit their brain’s magma and it explodes like a volcano saying “WAIT WHAT!?”

Kundera describes the results of going from wondering to asking: “A question is like a knife that sliced through a stage backdrop and gives us a look at what lies behind it.” What lies behind may not even be an answer. Because that’s not always the intent anyway. It might just be a reminder that you’re resisting to orderliness of what we think we know.

There’s this crust of an ornery prick on my inner 4-year-old that wants to make everything make sense right away. I’m constantly trying to scratch away at it to let disorder just be for even few extra seconds.

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Wild Garden

Wild Garden is an exploration of how companies use strategy, creativity, and organizational culture to nurture growth. Organically fertilized by Ben Perreira.