Of the standard questions, “why?” is the best. It’s the most interesting; it’s the one that affords the best answers. When I was in Grade 6, Mr. Whitaker said he was going to write a question on the board. He said that it was an actual question from an exam he did in university. He said that over half of the students in his philosophy class failed this exam — which was made up of the one question.

We 11- and 12-year-olds marveled and shivered at this prospect — we were getting a university-level assignment. The few keeners in our class (I was one of them) were very excited by this, while others were suitably unimpressed.

Mr. Whitaker turned to the blackboard and wrote the question. The question was one word long.

Why?

We were a bit flummoxed. Of course we were — we were kids. I honestly don’t remember what anyone else did, but I sat there and stared at the board like I was stoned. I understood that this was a puzzle, something to be figured out and not merely answered, but I didn’t get it. I did, however, get Mr. Whitaker, who was my teacher in Grade 6 and Grade 8.

People started shooting their hands up and saying things. No one was right.

I put my hand up and got called on. “Because,” I said. Mr. Whitaker told me I’d get 50% on the exam.

Turns out the answer, or at least the answer he was going for, was “Why not?” When I got older, I heard several versions of this story from friends and classmates — with good reason, considering its provenance. It is unlikely that Mr. Whitaker actually experienced the one-word exam, but the idea he planted in my head was worthwhile nonetheless. I started looking at problems in a different way.

In Junior High, my favourite few minutes of the week were when my advanced math teacher, Mrs. Johnson, used to give us logic puzzles. You know the kind: A man is found dead in a room surrounded by 53 bicycles — what happened? Stuff like that. It helped me nurture that thing I had been given, that desire to look at things cockeyed.

As I got older I really started to see the wisdom in trying to solve problems using non-linear thinking. These days, when I try to solve a problem for a company, brand or organization (or even with respect to beating an opponent at fantasy baseball), I try to employ the same kind of thinking. When I meet people that think like this, I rejoice. I feel whole. I also feel less lonely; being the left field, different, dissenting voice is lonely work.

This is among the reasons why I badly want to meet Steven Levitt.

While it isn’t a hard-and-fast rule, the less traditional a potential solution is, the more interesting it is. I’m not one to eschew straightforward thinking when the situation clearly calls for it, but it never ceases to amaze me how often people in business silence the voice that is saying the weird, new, different thing. And of course I say that because it’s often me (or someone I think is like me, or that I am like) being ignored or rebuffed, but still, with respect to marketing and advertising — especially social/digital marketing and communications — I’m continually shocked by how traditional and safe the thinking is, and even more shocked that account managers (and their ilk) are surprised they aren’t getting the ROI and ROE that they want.

“Traditional” isn’t meant to be a stand-in for “boring,” here, although a lot of times traditional, safe approaches are boring. I’m merely suggesting that a lot of agencies consider themselves avant-garde, outside-the-box thinkers when in reality, they’re really, really not.

Where are the visionaries, the weirdos, the square pegs in round holes? I’m looking for them; I’m looking to join them. I want to be one of the people asking “why” instead of one the people trying only to not to get fired.

This is the third post in my #30posts challenge. Don’t know what that is? Read this.