Learning Illustrator the wrong way the right way
I’m learning Illustrator the wrong way the right way.

As someone who grew up never taking the time to actually read instruction manuals, I just don’t really know of any other way to learn something other than doing everything wrong until you realize you’re all of a sudden doing everything right. At least, right for you.
And I think that’s the key: true learning is not about getting everything “right.” In fact, to be creative requires doing things differently. So you can really argue that learning everything the “wrong” way from the beginning is one of the easiest ways to ensure your work will stand out.

Obviously, there’s always the danger it will stand out in bad way: it could be really terrible. But then, hey, doing things the wrong way is actually the fastest way you’ll ever learn what’s for you and what’s not.
There’s a famous Picasso quote that’s all over the Internet these days:
“Learn the rules like a pro, so you can break them like an artist.”
It’s one of those generic creative mantras that startupers like me love. I mean, let’s be honest, who doesn’t like to think of themselves as a “pro” and an “artist?” But there’s always been something about this quote that struck me as missing a step. How do you start learning the rules like a pro when everything you touch to actually start learning it breaks when you touch it?
Believe it or not, the answer to this missing step that sounds truest to my ear cropped up when I totally messed up the quote, telling it to someone once. Ironic right? I accidently flipped it around, saying: Break the rules like a pro, so you can learn them like an artist.
But it struck me, maybe if we add something like: …then keep breaking them anyway, we have our answer.
Break the rules like a pro, so you can learn them like an artist…then keep breaking them anyway.
The point is: what if learning the rules like a pro is necessarily a cycle of breaking, making, breaking, making.
Let me bring in another quote to put it differently. In the middle of Graham Greene’s “The Destructors,” we get this:

“Streaks of light came in through the closed shutters where they worked with the seriousness of creators — and destruction after all is a form of creation. A kind of imagination had seen this house as it had now become.”
So, back to Illustrator. Here’s the scene: streaks of light are coming through the window as I work with the seriousness of a creator on my laptop. I’ve been at it for a few hours working on a logo that’s for a concept I’ve been putting together called Horizontal. (Here’s the first sketch on Dribbble.)
And this is what I’ve got:

It’s a mess, it’s a jumble of too many rectangles, too many little touch-ups with the pencil. This is not how you “do” Illustrator.
But the trick is, this destroyed view is not the whole picture. The destruction is all behind the scenes. The only way you’re seeing it is because I’m sharing it. Otherwise, when you look on Dribbble, this is all you see:

Destruction is a form of creation. Learning is doing it the wrong way long enough until it becomes the right way.