Some form of gnosis or immediacy is attached to all thinking as its root-form or primitive origination; every act of thinking has this passive derivation, this coming-into-being of thinking not out of nothing (as it likes to imagine) but out of some unthinkable something. But the most self-abstractivist or self-reductivist kind of thinking cannot tolerate even the notion (much less the traumatic experience or confrontation) of an incurable pathos, a weakness or blind-spot, within consciousness. The very idea is an insult to the autonomy or self-determinability of ego/will/reason.
People who turn to philosophy expecting to harvest a crop of formulas of wisdom or understanding do not understand--philosophy has such things, but they are merely incidental, not the essence of the matter. Philosophy is about subtilizing and tuning up the coherence and acuity of one's seeing, it is about opening new dimensions for insight, learning to think about what one is doing when one thinks instead of just blundering through the processes of putting thoughts together.
All that the posture of skepticism accomplishes is to freeze the ego in an ignorantist poverty that never stretches or diversifies its resources of imagination or understanding. Any uncultured cretin can close his eyes and try to reduce the issues down to linear simplisms and say, "I am doubting, I am proving my magisterial or sovereign control over my own mind." Doubt is a useful and significant test of one's critical powers, but by itself it bears little if any significant cultural charge of enlightenment or satori; indeed it is the very opposite kind of thing.
Because of the very intimate character of philosophical norms and criticisms, a teacher in philosophy has to be like Alexander the Great: never issuing dictates as to what his soldiers ought to do that he was not ready and willing to leap into doing himself. An excellent teacher is one accomplished in serving as an exemplar, every act of every kind of thinking and every form of perspective must be something he is prepared to illustrate by carrying out himself. Students need to see the incandescent arc-welding that joins ideas together into thoughts. If one is saying something that inflicts suffering, one by all rights had better be prepared to suffer along with the student, to sympathize and assure them that the profit for this agony consists in freedom and clarity.
Thinking is the subtlest form of self-polemics, the art of a certain finesse in psychological self-vivisection and self-crucifixion (Hegel of course called the path of self-disillusion the via dolorosa or "highway of despair," in Baillie's fine and florid rendering, like Jesus' route to Golgotha).
In spite of the ancient roots of skepticism--all the way back to the radical Sextus Empiricus and beyond, to Parmenides and Zeno--"doubt" remains a constantly miscomprehended action and posture. Doubt is a state of the suspension of both belief and disbelief: many people assume that thinking has only two positions, positive and negative, and if you doubt something you are disputing its validity or positing the contradictory position. This is disputation, not doubt. Doubt per se questions the form or content of what has been asserted but it itself is a freeform state of wondering what the general parameters of the issue are and how it most rationally ought to be framed. Such particulars as most people are familiar with--position A or not-A, conservative or liberal, Christian or atheist, etc.--are never authoritative or exhaustive alternatives for a truly thinking and creative or radical mind (determined to go for fundamental principles, not their peripheral consequences or specific applications). They are "stock fallacies" or forced choices.
Those who have chosen the path of least resistance in life, who cannot bear to bring themselves to make a stern value-judgment in criticism of their own most intimate feelings, achieve what they deserve: not self-understanding but radical self-superficialization, not a discovered but a self-ascribed identity that explains nothing, reveals nothing, means nothing, and ultimately accomplishes nothing culturally or intellectually.
Sadly the very thing that strikes us as obvious always defeats our thinking about it in more penetrating ways: just as the Romans said that "the good is the enemy of the better," so too "the self-evident is the enemy of the very process of clarification or understanding," not to mention the enemy of the "transcendent or ultimate."