It is very hard to maintain hope and confidence in the face of seemingly unrelenting rejection and disappointment. Whatever one’s theory about the difference between Luke’s ‘poor’ and Matthew’s ‘poor in spirit,’ I think both phrases are rather apropos for those who are job-seeking. It is harder to believe the predicate of both phrases, however (“for yours/theirs is the kingdom of heaven”). There is nothing uplifting about the experience, and it more likely to produce despair and lack of valid self-confidence than it is humility.
I must admit I deeply envy Kierkegaard for having inherited a vast enough wealth that he could study and write without concern for things like food and rent (and Sallie Mae…). His work may have used up his material resources by the time of his death, but that is better than digging a hole from which a recession makes harder to climb out.
Kierkegaard had a lot to say about despair (particularly in his Sickness Unto Death), and in his analysis it is primarily to do with failure to rest in G-d and to be authentically ourselves before Him. In many ways, it is rather prescient. In others, however, it does nothing to make the latest rejection letter seem any more of an easy thing to accept.
I can accept and understand despair as a result of incorrect pride and lack of G-d-centered self-esteem. I have more trouble with understanding and coming to terms with more circumstantial (rather than “existential”) prompts towards fear of utter failure.