If you're facing rejection right now, it's very important to realize, especially in a down market, that it's not personal. Really. Truly. The indifference of the system is also crushing. But perhaps it's better than thinking that someone was out to get you. It's very hard, after such a long and painfully exposing process, to digest the wounds. Give yourself a break and stop ruminating about it.
I've had all kinds of feedback as to why I didn't get a certain job, though seeking feedback is risky. I'd avoid it if I were you. It may only confuse the issue. One guy said “Well you do cultural studies,” to which I replied “No, I don't”—to which he replied, “You say your work draws on it”—to which I replied, “Did you read past page three of my book?” End of conversation.
There are some structural reasons why things suck. I'm looking at you, Ivies. They tend with very few exceptions to hire their own. I remember when I was at Princeton, doing a postdoc, I wasn't allowed in the job applicants' workshop “Because you're not from Princeton.” Coming from the UK where there is a totally different culture, that sucked to say the least. Another place said I was “overqualified”—that was Yale and I nearly did myself in when I heard that one.
Because of this, the Ivies are missing out on some of the most imaginative, creative work that happens in the humanities.
Somewhat selfishly perhaps I like to think that the best people sometimes take a few goes to get a job. Especially if you're fighting self esteem issues or some other urgent emotional issue, as I was.
I used to keep a folder with all my rejection letters in it—a few years into having a job, I burned it. There's always next time...
Find some allies. Assemble your team. Make sure your letters really rock. As placement officer at my school I can tell you that some students make bad choices about whom to ask for letters. If your recommender isn't writing about 3 plus pages for you, you should think about changing them or talking seriously with them. There's an absurd rule: if I praise you highly for one page, I'm saying you shouldn't really be considered. If I praise you highly for two pages, there might be something wrong with you. Three pages does the trick and four pages says “This is the best student ever.” Sorry dudes that's the American way.
HT to Adam Kotsko who inspired me to put this together, somewhat late in the day.