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I’ve spent my whole life asking the wrong question…

I have an uncomfortable confession to make. You see, I was born with a question on my lips and I’ve spent pretty much entire life trying to answer it. Which is why it’s been uncomfortable for me to realize in the past month or two that I’m pretty sure I’ve been asking exactly the wrong question all my life.

That question, by the way, is “why?”.

Since I was first old enough to formulate this question it has plagued me — amounting to a total span of time far greater than the normal four-year old fixation.

One of the lovely women I coach with has dubbed me “the one with a hypothesis for everything” — and it’s so true.

Every mystery, every puzzle, every question — I am fixated, transfixed, addicted. I chew them over and over in my mind, obsessed with figuring out the why of things until I happen upon a plausible explanation. Only they is my curiosity sated.


As I’ve been thinking about 2016 and what I want to do in the coming year(s) of my life, I’m starting to realize that the question “why?” is ultimately a trap.

“Why” leads invariably to a line of questioning in which the world becomes an murky, impossible place and every decision is weighed down by 10,000 confounding variables.

Under the burden of “why?”, even the simplest decision becomes impossible.

In deciding what to have to dinner one must know why chicken might be better than beef, why Indian food might be better than Chinese, why it might be important to buy organic, etc.

Under the burden of “why” a decision cannot be decided under the auspices of reasons such as “because I want to” (why?) or “because it sounds good” (why?).

Instead, a decision must be infinitely logical and well defended. Under the burden of “why?”, all possible reasons must be vindicated and validated and living your life rapidly begins to feel impossible.

Which is why I’ve decided to start asking a new question: “Why not?”

It’s possible that I find this magical just because I’m going through a phase of some sort… but bear with me for a second if you’re feeling skeptical.

“I feel like having chicken for dinner.” Why not?
“I think I’ll meditate this evening before bed.” Why not?
“Should I skip class tonight and go to bed early?” Why not!

“Why not?” is almost always immediate permission to move in the direction you wanted to go anyways.

As a coach, this is probably something I should have figured out a long time ago — because I ask my clients why-questions a lot in order to help me understand how they see their world.

But I don’t ask “why?” or “why do you think that?” or “why is that?” very often.

Instead, I usually ask questions like “why would that be bad?” or “why would that be a problem?” or “so what?” or “who cares?” (or “why *not*?”!).

When we ask ourselves these “why not?” questions we can see immediately to the heart of the matter.

Because the answers that come up are always are excuses.

“I might fail.” “It’ll never work.” “I’m not qualified.” “I ate chicken last night.”

And our excuses are almost always… well, pretty darn lame.

But sometimes they’re also not lame and that’s fine too.

If doing something really is a bad idea then you’ll figure that out when you ask “why not?”.

That’s the brilliance of the question, really. It’s just waiting for you to look your choices in the eye. It doesn’t have any sort of an agenda.

Now it’s your turn! I dare you to pick a dream for 2016 and ask yourself “why not?” Let me know what comes up for you in the comments!


One comment

  1. phillip says:

    That is a terrifying concept. (Not bad, just terrifying). It places so few constraints on life. I would fear getting lost and wandering aimlessly forever.

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