Ask the (Dumb) Question

Don’t be afraid to ask the “dumb” question.

I was reminded of this wisdom today while reading about Malcolm Gladwell in Tim Ferriss’ “Tools of Titans.”

Gladwell, the author of renowned books such as “The Tipping Point,” “Outliers” and “David and Goliath,” has built his career on asking questions — a skill he learned from his father.

Apparently, Gladwell’s dad, a highly educated mathematician, had no concerns about coming off as foolish.

If he didn’t get what someone was talking about, he’d keep asking questions until he did.

“I don’t understand,” he’d say. “Please explain it to me again.”

As Gladwell points out, his dad never would’ve invested with Bernie Madoff, because he’d have kept leaning on Madoff’s house of cards until it fell over.

Doing this requires a blend of awareness and obliviousness, as well as an uncompromising confidence — a combination I don’t possess.

I’m too aware and too unconfident.

The old saying goes that there’s no such thing as a stupid question.

It’s been my experience — as I’m sure it’s been yours — that this saying isn’t always true.

And unfortunately, those experiences have seeped into my bloodstream, infecting me with fear.

I’m terrified of being thought of as stupid.

Though that’s a reasonable concern, it’s not a healthy one, as it’s curbed my curiosity and capacity of comprehension.

Which, ironically, has made me stupider.

Which raises the question:

Why do I keep (not) doing this?

In terms of what I should start asking, that needs to be at the top of the list.