I’m an optimist, but in the long-term sense. Short term pessimism is not always inappropriate. (Things have the potential to get fucked up for a while.) But long term optimism is usually the default condition. (Things got better, lessons were learned.)
All you can do is try to anticipate the possible downers, and have fall-backs in place to mitigate the damage.
For the really serious shit, keep your gas tank full. Have a passport. Hide enough cash in your house to cover everything for a month or two, and at least one Krugerrand (that’s not a gun, but one of those might be useful, too, if you know how to win a firefight.) Make sure you have good walking shoes and calculate how long it will take to walk to Mexico. Sleep on the ground in the backyard a couple of nights, just for drill. These are things that require no serious investment, but your mindset ought to include them.
If none of the above items are required, then you’re sailing on decently calm water and your own resources ought to be enough to get you over humps. Optimism should need little more than a sense that you have the resources to get over the humps. And Yes, you wil take some losses. If you think you cannot get over it, you have just become your own worst enemy.
“Lost a lotta fights, but I learned how to lose OK” – Billy Joel, “Keepin’ the Faith”
I find cynicism more helpful. If you have low expectations of a movie, for example, then when it sucks it’ll just confirm your prediction and give you a smug sense of satisfaction. This attitude probably won’t win you too many friends, so best not to advertise it too much. But if the movie is actually decent then you’ll be pleasantly surprised. If you have high expectations you’ll invariably end up disappointed. Maybe this isn’t true cynicism, which would be thinking the movie will suck anyway and not going to see it. Or seeing the movie, but looking for every little flaw and nitpicking it to death. Not sure what else to call it, though.
I’d call it “having low (or modest) expectations.” And, as you note, if your expectations are too low it’ll keep you away altogether. Plus, if people expect to enjoy something, doesn’t that predispose them to enjoying it and make it more likely that they will?
Definitions of cynicism that I’ve found say that it’s “an attitude or state of mind characterized by a general distrust of others’ motives” and has a connotation of contemptuousness, which I don’t think is what you’re talking about (and I don’t think is helpful as an overall general approach to life).
I look at where we were, at any time in history, and I look at where we are today, and I see that we have improved tremendously the conditions in which nearly everyone lives.
We have obstacles to overcome, and even setbacks in which we need to retrace our steps, but I have always been optimistic that on balance, tomorrow will usually be a better day than today.
I am often a realist or even a pessimist when it comes to specific actions, tasks or candidates, but I always hold out the hope that we will persevere and continue to build upon the successes of those who came before us.