I wrote in my last post that skepticism may be rooted in a desire to avoid tragedy, to the extent that tragedy is the product of stubbornly insisting on the universality and rightness (and righteousness) of what turns out always to be a partial and flawed view of the world.
There is a problem with the desire to avoid tragedy, of course: the easiest way to do it is to just not give a damn about anything. Historically, perhaps stereotypically, skepticism has always seemed to slide into quietism, complete passivity and indifference in the face of whatever happens. How do you know it matters, anyway?
Hume pointed this out, and also noted the tragic flaw in the avoidance of tragedy: quietism can only result in extinction. Failing to choose and act at the right moment can also have tragic consequences. We have to act, in spite of our doubts, in spite of our fear that we may be acting on a partial and flawed view of the world.
Nietzsche would say that we need our illusions (read: our mental models that make meaning for us, however partial and even deceptive they may be) in order to live. To strip away all of our illusions is the cognitive equivalent of stripping the atmosphere from the Earth: both make life impossible. (I can't remember where Nietzsche appeals to this image - perhaps in The Gay Science?)
So, how to be a skeptic and live?
Perhaps it's a matter of having a finely-tuned sense of irony, feeding into an intellectual modesty that feeds in turn into practical caution . . . but not too much caution.
At work, I am surrounded by Pragmatists, in the sense that many of my colleagues do work informed by Peirce, Dewey, James and the rest of that lot. Some of their ideas have started to inform my own work, though I'm still a hold-out for Continental approaches to the same problems. The main idea I take from Pragmatism is the usefulness of an experimental method: by all means, choose and act boldly, but recognize that you are acting on a hypothesis that may be subject to revision.
Being a skeptic, like being a pragmatist, requires intellectual agility and a sort of practical wisdom that Aristotle might recognize right away: do not overcommit to a particular way of viewing the world, but do not undercommit to it either.
Being a skeptic also means recognizing fully that, however hard we try, we cannot really avoid tragedy, even if we can improve our odds a little.