I have a reputation, in my social and professional circles, for being something of a curmudgeon.  

I find this to be roundly unfair. 

Okay, yes, over a pint, I'm more likely to argue with you than agree with you, that's true.  And yes, I tend to be rather critical, and vocal, about things I think could be going better.  I just like to be convinced of a thing before I believe it.  But once I believe a thing, I become its earnest champion, arguing for it and vocally criticising all that...

Okay, perhaps they have a point.

I know the exact moment when I turned.  I was standing at a podium in high-school.  My first debate.

Debate

For the uninitiated, formal high-school debate, the kind the National Forensic League gives out certificates of achievement for, is a peculiar institution.  

It's a highly structured speaking format with lots of rules and lots of insular jargon.  It has about the same relationship with a lively argument as chess does with a fist fight.

There is a resolution is chosen at the beginning of each year that forms the major premise for all of the debates that follow.  My year it was (from Wikipedia): "Resolved: That the United States government should reduce worldwide pollution through its trade and/or aid policies."

An Affirmative team posits arguments in favor of the resolution while a Negative team looks to undermine or refute their claims.  Judges decide a winner based on whether enough of the Affirmative team's arguments are left standing after a few rounds of discussion.

The peculiar part is that to win, you don't have to be right.

Instead, the goal was to be the one with the best Evidence.  Each team in a debate brings with them great stacks of index cards with bits of text glued to them.   These make up all the arguments, counter-arguments, counter-counter-arguments, and counter-counter-counter-arguments that you'll need.  The best teams obsess endlessly about Evidence  and you could generally size up an opponent based on the size of the stash they hauled into the room with them.

Back to the Podium

I was on the Negative.  I'd just heard the Affirmative opening arguments, something about how the US should promote nuclear power, and being pre-curmudgeon at that point, I was quite inclined to agree with them.  Their points seemed perfectly valid.  Nuclear power seemed to be an elegant solution to the world energy problem.  While it had/has problems to be addressed, there's no reason why these technical problems couldn't be solved, in time, with better technology.

I suppose I could have just walked off and dropped the class, but I recognized this as a game, and I liked playing games.  I was good at games.  And also being a good student, I had collected many pieces of Evidence to counter this specific argument, so had a chance here and now to win the argument, even if I believed I was wrong.  

So I launched into a rebuttal of each of their arguments, hand waving and pausing for effect while the Affirmative team scurried about trying to find the index cards with the right counter-counter-counter-counter-arguments.

We won that debate.  My partner and I won all the debates that year.  

(This is nothing particularly to brag about.  This was debate class, not debate club.  The bush leagues of debate.  My teacher later lobbied me to join, but I ignored him because it would have interfered with football, which TV had lead me to believe led to girls, and, well...puberty is its own best rebuttal.)

It was at that moment, for something as silly as wanting to win a game, I began to learn how to suppress my emotional and subjective beliefs from the exchange of purely objective ideas.  Or perhaps more properly, to temporarily direct and shape my beliefs towards a contrary viewpoint to allow me to argue it more strongly and convincingly.

Pessimism About Products

As it turns out, this is a wonderful skill to have.  

Very often, we are put in situations where our beliefs are put into conflict with cold hard reality.  The revenue projections that were missed, a heartfelt promise you made to your team but couldn't keep, or a customer looking confused and concerned at your product roadmap.

In these situations, there is a strong temptation to externalize and rationalize what has happened.  The market wasn't ready, the team didn't work hard enough, the customer just doesn't get it.  Its far better if you can be self-critical, take your lumps, and move forward with a newly straightened perspective.  Better still, if you can see ahead of time when your beliefs are leading you over the cliff's edge.

To an outside observer, this can appear to be pessimism.  Particularly if that observer shares the errant belief that should be changed.  

Most people loathe changing what they believe and fear the uncertainty that follows discovering that they are wrong.  They therefore loathe and fear the pessimist, who seems to be tearing away at the fragile veil that lets them act with confidence.

Those people squander confidence.  Yes, it can inspire a team to do remarkable things.  Terrible risks are sometimes only undertaken because of misguided confidence, and great rewards reaped as a result.  But if you deal in it, and it fails the test of time, you're marked a fool.  Being thought of as a fool is far worse than being marked as a pessimist.

Use confidence at the moment of truth, at the end, rather than the beginning.  When there's one last unimaginable leap to cross and you need the team to come with you.

Now, this isn't to argue that I should be forgiven all my trespasses as a curmudgeon.  I'm a creature of emotion as much as reason, just like the next guy.  Sometimes I argue out of bad habit, rather than any particular insight into a situation.  Sometimes I'm the starry-eyed true believer that can't see the imminent danger just in front of me.  

But, if you're not persistently and actively challenging your own assumptions, then you might try a little pessimism yourself.