Like other Greek Philosophies (Epicureanism, Stoicism, Hedonism), Skepticism was created as a way to increase our quality of life, though like the others, its name took on new meaning over the centuries.
Pyrrho of Elis had supposedly traveled to India with Alexander the Great and his exposure to Vedic philosophy is meant to have profoundly influenced his worldview. Upon his return to Greece he codified his philosophy: To attain freedom from worry (ataraxia), we must realize that our opinions about the world are highly provisional and as such are prone to disappoint us. Therefore the way to true contentment was to withhold final judgment on all things. By not holding to any particular belief or expectation, one could not be disappointed when they turned out to be false. This he called Skepticism.
Since none of his original writings remain, most of what we know about Pyrrho comes from second-hand sources, and the skeptic philosophy which bore his name: Pyrrhonism. Today, the word skepticism has less to do with enhancing quality of life, and more to do with assessing the validity of a rhetorical argument.
Applying skepticism to our daily lives can be difficult in a day when everyone is supposed to have an opinion about everything, even if they know nothing about it. However, this only underscores its importance. Saying “I don’t know, sir” can be one of the most intelligent (and heroic) things we can do. As Taoism suggests, it’s only when our cup is emptied that we have any room for new liquors.