Woody Allen says “there are two kinds of people in the world, the kind that say there are two kinds of people and everyone else.”

And it is extremely helpful – almost essential from time to time – to divide things into categories. Dress socks in one drawer; athletic socks in the other.

It’s only a problem when you start acting like the categories you invented are “real” – out there in the world differences in essence rather than handy (and temporary) labels you hang on wildly different things just to get a handle on them.

It’s easy to recognize how stupid this looks when other people do it. George W’s “either you’re for us or against us” foreign policy was the source of well-deserved ridicule. When we create similarly ridiculous choices for ourselves, though, we say we’re being “realistic.”

Sure, even the most die-hard binary thinker will probably admit that it’s not all black and white; there’s always a grey zone. But if you tend to think “either/or”, you imagine that the grey zone is the result of sloppiness. Ideally, it should be black and white, but, hey, no one’s perfect. So we tend to ignore the grey like a rounding error.

But this kind of thinking not only blinds you to a part of reality – it blinds you to the most interesting, fruitful, productive part of reality.

In life, as in all natural systems, the real action is always at the border. The vast majority of all ocean life lies along the continental shelf, even though it accounts for only a tiny fraction of the volume (or area) of the oceans. The difference between a 20⁰ and 21⁰ bowl of water is pretty uninteresting – but what happens at the one degree difference between freezing and fluid is amazing. Usually the solutions that people are looking for live in the grey zone, where things are both/and, not either/or.

Now, to be clear, I’m not suggesting a regression to the mean, the intentional creation of a taupe world that tests well with focus groups. This isn’t about averaging black and white – it’s about finding the thing that’s black and white and red all over. It requires doing a Hegelian twist on your thinking – of forcing your mind to start to find the synthesis of both a lion and an eagle; of both a phone and a computer; of doing what you love and being paid well to do it.

One technique that facilitators learn early in their career is to replace the word “but” with “and” whenever they hear it. “But” always points to one of these false either/or choices and sometimes just saying “and” instead gets your brain thinking about more interesting possibilities.

“I want to change careers but I’m 40 years old” turns into “I want to change careers AND I’m 40 years old.” All of a sudden, you can start to think of “40 years old” as an asset instead of liability. It can be something that supports changing careers – wisdom, experience, connections – instead of preventing it.

The real irony is that it looks like Woody Allen is right. I often feel like I’m an alien from a different planet when talking to the binary-intensive. My vibrant 3-dimensional world full of possibilities turns into a bizarre, colourless 2D version of false choices. Same planet, different worlds.

The challenge, I think, is figuring out how to highlight those times when we’ve all successfully lived in “Both/And” World, and consistently call into question that limiting “either/or” thinking in ourselves and our colleagues. I think we can all grow the ability to hold the creative tension of two seemingly different things and allow that miraculous third thing to be born. But it takes work and discipline and someone to question the “either/or” options whenever they are presented.

Because after all, there are two kinds of people in the world, and I’m that other kind.

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