The Why of a 5-year-old ~

Oliver Keller
Oliver’s Blog about Nothing
3 min readOct 29, 2018

Does anyone know how many books were written about “The Why,” like “find your why,” or “live your why,” even “why ask why”? So you see the list goes on and on. How many have you encountered? Hundreds? Thousands? They all have one thing in common, and that is some sort of greater understanding of how your why, will help you get to know yourself better and guide your future self.

The why I found most interesting is the one taught to me by my son Jake when he was 5 years old, freshly moved into my house after his mom and I were newly engaged, 9 years ago. His why is best described as a why to the power of frustration. You know its that why that starts like this “Hey buddy please don’t leave the door open because the doggies will escape and run away,” “Why?”. “Well because they are runners and like to chase things.” “Why?”. “Because that’s what dogs do.”. “Why?”.

At this point, you can see where this conversation was going and who the clear winner of it would be. Hint, not me, because after the 15th why or so, honestly I lost count at about 10, I just pulled the old parental go to “because I said so.”

Yippee, I won because that last statement was it, it gave me all of the power, dare he try and stump me, oh no not today. After I was done gloating and celebrating my battle victory over a 5-year-old, I realized that I lost and lost big. I missed the ability to understand his need to know why. Here is a 5 year old and his inquisitive nature at full throttle.

His why’s were not designed to frustrate me or challenge my authority, plenty on that later, but an attempt to gain a point of reference, to draw a complete picture if you will, of how leaving a door open could possibly have all of these consequences. He merely kept asking, because I was more than willing to add more and more reasons to showcase my superiority of logic and language, yet what I achieved was shutting down a curious, naive and unspoiled mind, all because of my ego.

I would challenge at this point that my ego is actually synonymous with fear. The pure horror of not having an answer. What would have been the worst thing to happen if I would have just smiled and looked back at Jake, shaking my head in admiration and said: “Buddy I have no idea, I really don’t know, THAT was a great question.” It’s funny to me now as I have grown in my ability to take my ego and bring it down to my heart, and therein lies my one take away.

I made up a story in my mind that somehow having to admit, that I did not know the answer, would poorly reflect upon me in the eyes of my 5-year-old stepson. How could he respect me if I failed in my first conversation with him? How could he ever come to me again and seek my council since apparently, I did not know the complicated answer to such a simple question?

Take Away:

In all actuality, my story could have become a self-fulfilling prophecy, because going for the “win” actually made me less approachable, than showing vulnerability and honesty. My ego was uncomfortable with not knowing, whereas my heart saw it as the moment to teach. Teach him that not having the answer is ok. Teach him its ok to laugh at oneself. Teach him that the why question is powerful and encouraged because it is what builds a framework for understanding. So when you feel yourself telling yourself a story, challenge yourself to remove your ego and bring it to your heart but merely focusing on the facts. For me it was just that Jake was trying to learn and understand. That’s it. The end.

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Oliver Keller
Oliver’s Blog about Nothing

Managing Partner & C.E.O. of Synlio. Synlio addresses one inarguable fact, #RFPsSuck. See how Synlio’s RFP Automation solution has reimagined the RFP Process.