The Optimist and Two Pessimists

A pessimist sees the difficulty in every opportunity; an optimist sees the opportunity in every difficulty.

-- Winston Churchill, as parroted by the stupid "Daily Words of Wisdom" toy on my boss's desk.


I never liked this aphorism. While it probably isn't untrue in and of itself, it and the reality it implies seem mendaciously oversimplified to me.

Why praise the optimist for seeing things one way and scold the pessimist for seeing things differently? A person's perceptions only matter inasmuch as how they inform how he acts.

The person who notices the silver lining isn't necessarily going to be a happy and successful go-getter as Churchill connotes. And the person who sees the cloud might not be a morose layabout.

Churchill presumes the pessimist's tendency to expect an undesirable outcome will paralyze him, inhibit him from running for the door when opportunity comes a-knocking. It very well could -- but the same logic, we can surmise that the optimist will commit himself too quickly, too eagerly. He'll be the guy who invests all his money in a tech start-up that never breaks even; the kid who doesn't do his homework because he's sure of a snow day, but gets a flurry instead of a blizzard.

Success is always sweeter when you were anticipating failure. And defeat is always more bitter when you took victory as an assurance.

The optimistic writer receiving a hundred rejection slips for his screenplay is likely to feel the blow more acutely than the pessimist, who expected as much anyway. When he finds out he didn't get the job after all, the optimist is crushed. The pessimist stopped thinking about it a week ago and has been sending out more resumes.

What irks me is the fat man's suggestion that seeing the difficulty in an opportunity is failing. Since when is foresight undesirable?

More than the optimist, the pessimist can be expected to have a backup plan. When he embarks on a course of action, he's anticipating speed bumps, roadblocks, and detours. That usually means he's planning and preparing for them.

The pessimist is a fellow more likely to be carrying an umbrella during the rainy afternoon following a cloudless morning. The pessimist keeps a spare tire. The pessimist's heart is less apt to be broken because he's more cautious about placing it in someone else's hands. The pessimist isn't baffled when the protest march fails to change the world or make history. The pessimist understands the tendency of plans to go awry, the persistent difficulty of achieving a desirable (let alone ideal) outcome from any endeavor, and that things seeming too good to be true usually aren't true.

In this world, optimists are apt to be disappointed. And when you're expecting to find gold at the end of the rainbow and end up with the contents of a leprechaun's chamber pot, you'll probably think twice about following the next one.

It is true that many pessimists are former optimists. I suspect it would be a universal and inevitable transition were it not for the fact that some people truly are lucky and others have no sense of pattern recognition.

Broadly speaking, there are two kinds of pessimists.

One is the sort who expects that things will go wrong and people will disappoint him, and then takes pleasure when he's proven correct. I kept saying that people suck, everything sucks, and you see I was right. Hah.

This kind of pessimist is called an "asshole." It's probably the kind Mr. Churchill had in mind. And I would think a high percentage of the most insufferable assholes are former optimists who failed one too many times to temper their expectations. Ain't no one more bitter than a burned idealist.

The other kind of pessimist believes that things will go wrong and people will disappoint him. But he commits to them anyway, and rightly doesn't view the outcome he expects as the desirable one.

He deposits a can in the recycling bin and then watches it gets thrown into the same dumpster as the rest of the garbage. He asks out the woman for whom he's harbored a crush for years, and he gets turned down. He quits his job at the cannery in order to follow his dream -- open a restaurant, record a folk album, pursue a career in standup comedy -- and he doesn't make it, he loses all his money, and ends up back at the cannery after three years, older and a few grand deeper in debt.

But at least he was true to himself. At least he answered the call. And whereas the optimist who never doubted he was ordained for the golden one in a million may well be wrecked, the pessimist who hoped for success while anticipating failure will put on the wipers and keep on truckin'.

Because the wise pessimist knows that the right thing to do, the things he ought to do aren't easy and will probably backfire, but he does them anyway.

This sort of pessimist acts like an unburned optimist. He sees the difficulty in opportunity, but says oh what the hell and runs after it anyway -- albeit with some prudent reservation, and with an eye for pitfalls that the callow optimist often lacks. He appreciates what it means to side with the angels in a world run by demons. He understands that survival is necessarily a upstream swim, and the current is a strong one. He is gentle with others because he knows how flawed and fucked up people generally are, and can't hold it against them because he himself is a flawed and fucked up person.

I'm not sure of the term for this stripe of pessimist.

The word "idiot" comes to mind.

The world could probably use a couple more idiots.