the beauty of kierkegaard’s work for me is that even though he accepts hume’s radical skepticism about the ability of our thoughts to capture an external reality, he does not allow this to throw him into the pit of despair. the question for me now is how can i face each and every one of my experiences — turning away from any a priori “should” and towards the opportunity for emotional growth?
so tell me something right now without thinking: “why,” are you trying to communicate?
metonymy4u 
‘Despair’ is a key aspect of kierkegaard’s work; could you offer some context/an excerpt to support this assertion? He is, and we ought to be, very interested in the ‘should’ — towards becoming, but not something we define for ourself, but by reaching for the infinite: the ‘leap to faith’, or to becoming an individual.
The ‘why’ is very important; I only ever communicate because of some why in hopes of gaining some what which is just that little bit further along towards that.
I totally agree that depair is key to his work. In my experiencing of Kierkegaard he is responding to Kant and Socrates’ notion of the lack of knowledge to guide human affairs. The problem facing modern humans is that we have spent thousands of years figuring out that we don’t know anything for sure, and that we are alone in the universe. So the realization opens us up to despair, and we fall into that despair when we fail the test of modern life and succumb to the forces of modern intellecutalization, sytematization and the meaningless mouthing of the words of others. I think this is what I meant when I referred to the “pit of despair”–from Kierkegaard’s point of view, on my poetic interpretation of him, the pit was all around him in the way in which people just were following the crowd and not expressing anything personally meaningful to them. In fact, they had lost the habit of believing that knowledge was the task of a lifetime (as Kierkegaard mentions in the opening to Fear and Trembling) and instead believed that they had “arrived.” Ironically, this was brought about by just the enlightenment spirit which was originally an attempt to answer the nihilism of empirical philosophies. But by enshrining once again our cognitive capacities (as opposed to our aesthetic, ethical or spiritual capacities) and our ability to know the absolute truth, Kierkgaard sees, and Nietzsche later on agrees, that we have unstrung the bow of striving and ended up back in a mutated form of nihilism that Kant, I truly do believe, was trying to avoid at all costs.