How To: Play the Devil's Advocate

We've all heard the expression "playing the devil's advocate." We all know who that person is in our lives and on some level we resent them and yet still appreciate their ability to challenge our viewpoints and make us think. I know that for most of my friends I'm that guy. The douche canoe who will, despite personal beliefs, almost always argue or propose the opposite point of view in a conversation. I know it can be annoying, but I want the world to know that I don't just do it to my friends. I do it to myself. Yes, that's right, somewhere tucked in a dark corner of my mind is that jerk face who just loves to argue the opposite point. I hate him almost as much as my friends do, but despite that hate I appreciate that he's there. It's like having my own personal (harsher than need be) therapist to tell me to suck it up, grab my bootstraps, and drive on.

But how do you do it, how do you argue against what you believe or challenge your own beliefs?

This answer isn't what I would call "clear." I think of every situation as a coin, that is, it's two sided (or sometimes more than two sided). Life exists in duality; to every yin, a yang; to every negative, a positive; and every peanut butter, a jelly. As much as it pains me to do it I always make an effort to look at the other side of the house before acting or speaking up. I can feel with the strongest conviction a belief but still see and value the other side of things... which isn't always a "good" thing. The problem with this is that it's possible to have conviction in the wrong thing, know it's wrong, and maintain that conviction. Playing the devil's advocate is just the starting block, it's what you do after you challenge yourself or others that matters. Do you analyze both sides and then do nothing? Do you tell your friend to see the other side and then never revisit the issue? If that's the case then you're arguing from argument's sake and not really being productive with your ability to play the devil's advocate. The right thing to do is to propose that opposite point of view and then re-analyze the position.

I'm very lucky to be able to do this for myself, but someone who does this better than I is my mother. She's always able to be the plus to my minus, the light to my dark, and so on. She's got this crazy ability to tell someone they're wrong, explain the whole situation from all sides, and then (in a way) change that person's point of view. I guess I've picked some of this up from her over the years and I'm thankful to have been exposed to and to (in my own way) share her gift. So if you want to know more, well don't ask me, tell it to my momma (but don't call her "momma," she hates that).