To the Drifters, Makers, Why-Askers, and Systems Thinkers…
John Cutler

Your post sums up my entire life experience. I have always identified as a “Why-asker”. But asking why is rarely welcomed. Especially if there is no answer. But asking why is the only way to ensure that we are solving the right problem, in the right way.

One of the patterns that I’ve noticed in my life goes something like this:

  1. I enter a new environment and I am ready to take on the world. It could be a new job, a new activity like stand up comedy, or even a new relationship.
  2. Immediately, I notice the obvious things that don’t make sense, but I don’t say anything because I am “new here” and don’t “understand the intricacies”
  3. Eventually I am no longer “the new guy”, and my why asking is welcomed as an asset. My opinion often sought but rarely acted on.
  4. Things start to fail, and rather than say “I told you so” I just stop asking why or offering my opinion on things.
  5. Because I stop offering my opinion, I start to be treated like an outsider.
  6. Time for me to find a new environment.