Pessimist or Realist?

The nice part about being a pessimist is that you are constantly being either proven right or pleasantly surprised.
~George F. Will, The Leveling Wind

My usual outlook on life in general tends towards cynical pessimism. Though it's the politically correct thing to be an optimist, I just can quite bring myself to jump on the pollyanna bandwagon.

I've always believed in the old Boy Scout maxim, Be Prepared. That is, I don't want life and circumstances to catch me with my pants down -- unless I'm having sex, of course.

I've always seen my outlook as being more of a realist, than a pessimist, per se. To anticipate and prepare for what could go wrong is just the prudent thing to do, in my book. If I fly low to the ground, it doesn't hurt so much when I fall, and it's quicker and easier to recover and start over. If I don't have inflated expectations, they I'm not so disappointed when things don't work out -- and pleasantly surprised when they do.

I'm not sure if a person's outlook on the world is genetic or whether it is learning from experience. Perhaps it's a bit of both, but I'd say that experience probably plays the stronger role. In my own life, I tend to be optimistic about things I generally have success with, and pessimistic about things that end in disappointment more often than not.

I am optimistic about my relationships with women and I approach new women with confidence because a large percentage of my encounters with women over the years have been successful. Even when I bomb out with a particular woman, it doesn't get me down, because previous successful experiences tell me I'll likely do better the next time.

I am pessimistic about my chances of landing a good job and keeping it. This is because I've got a long list of shitty jobs that ended in disaster going back many years, And I've had to compete in a depressed job market more often than I've experienced a job market favoring job seekers.

In both instances, experience had shaped my outlook. In the instance of pessimism, one can endure a bad patch for awhile and still remain optimistic, but after a certain amount of time, optimism becomes denial.

I'll close with a bit of humor that perfectly expresses the idea that shit will happen despite the best of attitudes:

You put a drop of wine into a vat of sewage and you get sewage
You put a drop of sewage into a vat of wine and you get sewage.

Thoughts?