Seth Godin is really good at Pictionary. In fact, from what he says, he rarely loses (a fact also just confirmed by his son Alex).
This is how he does it:
Before the person drawing can even get their pen down to the paper, Seth starts shouting out words. He continues to shout out whatever words come to mind even when the only thing that has made it onto the paper so far is a single straight line. As the drawing takes shape, he continues with the barrage of words until he inevitably guesses correctly and wins once again.
Most people don’t play Pictionary that way. Most people hesitate because they are afraid of saying something stupid. They think, and pause, and edit. They don’t want to be judged. They’re worried they will say something crazy and everyone will laugh at them.
We all hesitate for that reason more than we think.
Try writing the words “I am afraid people will laugh at me” down on a piece of paper.
It looks a little ridiculous. Because, really, as a thing preventing us from moving forward, it kind of is.
Jessica Lawrence Quinn 
This makes me think of the scene in When Harry Met Sally and his Bruno Kirby keeps yelling out Baby Fishface! I’m guilty of this; I’m the person in the classroom that won’t ask the question because I think it’s stupid.
Yeah, that person in the classroom was always me too. I’m much more conscious now of trying to get past that.
Made me think of this picture: http://27.media.tumblr.com/tumblr_lh0spzz6wm1qbj8aso1_500.jpg 🙂
Love that Emily-Anne!
I’m the type of person who is really shy when I meet someone but once I’m comfortable with them I’m a huge ball of energy. I hate that there’s two sides of me like that. I’d rather be the fun, entertaining and witty me all the time. Which is why I signed up for an improv class. I’m working on coming out of my shell. In improv they have taught me to just say whatever comes to my mind (much like in Pictionary) and worry about justifying it later.
Right there with you! : ) The head of HR at my former organization would always joke that when he first met me five years ago, he thought I had no personality. After he got to know me well, he found out that I did in fact have a personality, and a pretty good one at that.
I don’t think it’s necessarily a bad thing to have the full depth of your personality revealed slowly. I think that actually can lead to deeper bonds with people.