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But Why?” Who knew that 2 little words could cause so much exasperation? But when you’re someone who questions everything, apparently it can get annoying to those you’re asking. Especially when their best answer is “Because“. According to those in the know, I’ve been a PITA pretty much my whole life.

As with many entrepreneurs, I have lived my entire life being a round peg in a world of square holes. Part of what makes us weird is a certain disregard for rules for tradition’s sake. It’s not that I ignored rules for the sake of mindless rebellion, I was simply on a constant search for what was best and most efficient. The idea of “we’ve always done it that way” is just stupid. I’m OK with rules, but they better be the best way of getting stuff done.

From my earliest days, I was a “problem student”. One time in the 1st grade, I came home from school and my mom asked if school let out early? Nope, somehow I hadn’t earned after-school detention that day! But, the the realization that I was “different” was in the 4th grade. Two things happened that year that have stuck with me to this day. One life changing event from the 4th grade involves the connection between discovering D&D and learning long division. But that’s a story for another day. So, moving on…

… the other life-changing event of the 4th grade was being designated a “gifted student”, which basically meant they took me out of class once a week for “special activities”

(Side note – I was the only non-6th grade student in this group, which might sound cool, but in reality it sucked. The other kids weren’t about to pay any attention to some “baby” two grades below them. Plus, being all my classmates assumed I was having an awesome time, and made their jealousy plain. Fun times.)

The problem was these “special activities” weren’t really special. Instead of building lasers, training monkeys, or field trips to robot factories, my “reward” for being “gifted” was just more school work.

But the one moment in this program that actually got me excited was when the teacher announced she had a special test from a “top art college” that would measure artistic aptitude. Well, that sounded pretty cool. It was small pamphlet with several “tests”. Just so we’re clear, I have the drawing talent of a comatose burro, but even at this young age I considered myself quite creative. And so a test to show show off my artistic aptitude to a real “art college” was quite the opportunity for 9 year old me. Once I got the pamphlet, I cruised through the various mini-projects until I reached one that said simply “Complete this Drawing” and below was a few lines that looked vaguely like half a sailboat.

But that was too obvious. I was here to be creative, right? So I contemplated that proto-drawing and what came to my mind was a turtle. So I used the existing lines to create the most awesome and creative turtle you’ve ever seen. I was so proud of that dang turtle. I turned in the pamphlet and waited for the praise to roll in.

As the teacher explained each mini project and the reasoning behind them, she came to the one I was waiting for, and explained that the “correct” answer was to draw a sailboat, and that not drawing a sailboat was wrong and showed a lack of artistic aptitude. Not only was I crushed, I was furious. All I could think as I sat there near tears was that it was idiotic to say that seeing beyond the obvious to do something unexpected, different, and creative was somehow un-artistic. 9 year old me realized in that moment that even adults, even “professionals”, could be just plain wrong. And I wasn’t about to let a standardized test tell me there was a “proper way” to be creative.

You know what? 9 year old me was right. Sometimes we need to break the rules, sometimes we need to draw outside the lines, sometimes we need to draw a turtle when we’re “supposed” to draw a sailboat. If you’re a round peg, and you don’t fit? Make your own hole.

PS if you’re the moron who created that art test –