Granted, I only went on the market once, and I'm not in the humanities, but this piece really details what it feels like to go through the job market.
It's exhausting. And while there are certainly things you can do to guarantee you won't get any calls or offers (like having no research in progress or sending out one-paragraph form cover letters), it's very possible to do everything (or most things) "right" and still not land any offers. This happened to me this year, it's true - but I also know a number of colleagues who are more accomplished than me who wound up with nothing to show for it ... or wound up with jobs way, way below what their accomplishments would suggest they would be able to get.
And even if you have a backup plan after you fail to get a tenure track job ... well, as the article says, you've now spent half of an exhausting year just sending out applications. Good luck finding any time to write more papers, prep a new class, or anything else that will make it more likely that you'll get an offer in the next academic cycle between April and August (when the market starts up again).
So maybe I really did fail ... maybe I didn't try hard enough, and maybe I just couldn't hack it in academia. That might be the case.
But I really don't care, at this point. I don't want to do the (full) academic market, ever again. It's a vicious cycle that relies on too much chance and far too much effort for minimal payoff. For someone who's compelled to teach and do research, that's wonderful. For me ... there are other things I'd be happy doing. I'm taking myself out of the cycle.
I want to feel happy when I get a job, not exhausted and guilty.