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  • Writer's pictureTucker Bryant

Why leaders and innovators should do riddles

I’ve got a riddle for you.






I’m gonna walk through the riddle right below this and will answer it pretty early on in the post. If you want to work through it yourself, don’t read on (yet)!

9 of 10 people who try this riddle will have a first instinct to try to solve it by trying to understand how the numbers are connected to the sports. (I’m totally estimating that number from my own guinea-pigging of friends, clients and other victims.) They ask themselves how many people are on a rugby team, or how many people are on a tennis court at one time, or how many points a touchdown scores. And that’s a pretty reasonable first instinct, right? You see some words, you know what they mean, so that’s the immediate way you try to “use” them in the context of this riddle. 

But upon doing that, these 9 people will quickly realize that that approach isn’t getting them anywhere. At that point, they have to take a step back from the words and look at them a different way. If they do that for long enough, they start to look at the physical appearance of the letters themselves. 

And soon, they start to count them in different ways. 

How many letters are in each word, what the letters “add up” to if we assign them all to numbers… and so on. 

And after doing that for long enough, eventually they’ll realize that the letters in the word RUGBY (in a sans serif font) have 9 “endpoints” (two on the bottom of the R, two at the top of the U, etc.) 

And after cracking the code, they’ll eventually end up at the end of the sequence and know with confidence that BOXING = 10.

Man, I love that riddle. 

But actually, it’s not just that one I love. 

In fact, anyone who’s had the distinct pleasure (slash semi-torture) of road-tripping with me for a car ridr longer than 3 hours will know painfully well my hopeless love for riddles. 

I think this hopeless obsession stems from a similar place as my love writing/reading poetry and for helping leaders embrace the weird in their cultures for the sake of innovation. Riddles — specifically ones that test our lateral thinking — challenge us to find different ways of looking at and using concepts that we’re often extremely used to using in one particular way. 

The riddle above is a great example. It makes total sense that the people who tackle it by asking themselves what the words “mean” do just that, because that’s how they use those words when they use them. But in order to see the riddle a different way, they have to take a step back from what their brain instinctively does when it sees them and search for new way of looking at them. 

When working with leaders, I often maintain that curiosity is the most foundational practice of creativity, in both art and business. It often manifests as a simple willingness to ask questions about how the “stuff” in our lives could be different. But it’s usually extremely difficult to develop this perspective when in the trenches of our work and routines — and much like what riddles force us to do, it’s necessary to take a literal step back from our usual obligations in order to develop a new perspective on them. 

In the context of the riddle above, “stepping back” means stopping our brain as it is thinking about the meaning of the words it sees. In the context of innovation, “stepping back” means creating time in our week that is guarded as being unstructured — time to do anything other than work. 

For my art and my work, if I don’t reserve at least 2 hours a week for this sort of white space, I know I’m missing out on the easiest, most reliable, and frankly most fun ways of taking advantage of my creativity. 

So give yourself a couple of hours every week to do something that’s not work. 

It may not feel like it, but that’s the time when your brain is doing some of the most valuable reimagining of your work it ever will. 

Basically, you get to prescribe yourself relaxation/recreation time and call it work. 

Which is pretty cool. And useful. So do it. 

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